bluuebunny/crossref_metadata_2025 huggingface dataset:
Experimental and Theoretical Study of the Cyclic Relaxation of Die Cast Magnesium Alloy
Authors: Xu Shu Sheng , Zeng Xiang Guo , Gao Zhan Hua , Chen Hua Yan , Fan Jing Hong
Published: March 2009

Magnesium alloys are among the best light-weight structural material with a relatively high strength-to-weight ratio end excellent technological properties. Therefore, magnesium attracts special attention of researchers working in automotive and aircraft industry. This work paid the efforts to the structural components made out of magnesium alloy AM60 such as chassis, transmission case in automotive, where the components are subject to cyclic loading after being pre-loaded. In this study, the cyclic stress-strain behaviors were investigated by strain-controlled fatigue testing. In order to investigate the effects of R-ratio on mean stress relaxation, the R-ratio ranged from 0.1 to 0.7 at the strain amplitude of 0.3%. The experimental results indicate that the mean stress relaxation increases with the increasing R-ratio. A constitutive model was proposed to simulate the mean stress relaxation. The calculation results show that the constitutive model developed in this work is capable of reproducing the stress relaxation behaviors of magnesium alloy AM60 under strain control.
Influence of Nanoparticles Modification on the Properties of Bitumen
Authors: Wu Shao Peng , Liu Gang , Wang Jin Gang , Zhang Yuan
Published: March 2009

In this study, the influence of some inorganic nanoparticles on the properties of bitumen binder was investigated. Three types of particles at nanometer level, calcium carbonate powder, graphite and carbon black, were introduced to modify bitumen respectively. The modified binders were prepared using a laboratory high-shear mixer. A dynamic shear rheometer (DSR) was adopted to characterize the properties of modified binders, including their rheological parameters and dynamic viscosity, over a certain range sweeps of temperatures, frequencies and shear rates. It was found that the addition of the nanoparticles increased the binder’s elasticity at low temperature which might negatively influence its resistance to crack. However the decrease of phase angle at high temperature might improve its deformation resistance. The shear rate dependence of dynamic viscosity for the binders depended on the type of nanoparticle. The research results indicated that the addition of nanoparticles to bitumen binder can change its physical properties to some extent and its potential should be researched further.
Influence of prey size and environmental factors on predation byPodisus maculiventris(Hemiptera: Pentatomidae) on viburnum leaf beetle (Coleoptera: Chrysomelidae)
Authors: Desurmont Gaylord A. , Weston Paul A.
Published: March 2009

Experiments were conducted under laboratory conditions to determine the influence of the relative sizes of predator and prey, temperature, presence of refugia, size of the search area, and host-plant species on the predation performance ofPodisus maculiventris(Say) nymphs against viburnum leaf beetle,Pyrrhalta viburni(Paykull), a new landscape pest in North America that feeds on the foliage of species ofViburnumL. (Caprifoliaceae). Predator handling time was positively correlated with body mass of the prey for all instars ofP. maculiventris,but the rate of increase of handling time relative to prey mass decreased as predator age increased. Temperature was positively correlated with predation rates, but the presence of refugia did not have an impact on predation. The influence of host-plant species and size of the search area was tested on southern arrowwood (Viburnum dentatumL.) and American cranberrybush (Viburnum opulusL. var.americanumAiton). There was a significant interaction between plant species and size of the search area, the species effect becoming significant as leaf surface area increased. In the case of southern arrowwood a negative correlation between size of the search area and predation rate was also detected. The identification of these factors adds valuable knowledge for usingP. maculiventrisas a biological-control agent againstP. viburni.
Toward management guidelines for soybean aphid, Aphis glycines, in Quebec. II. Spatial distribution of aphid populations in commercial soybean fields
Authors: Rhainds Marc , Brodeur Jacques , Borcard Daniel , Legendre Pierre
Published: March 2009

The study was conducted to document the spatial distribution of the soybean aphid, Aphis glycines Matsumura (Hemiptera: Aphididae), in commercial fields of soybean, Glycine max (L.) Merr. The abundance of aphids was assessed weekly at 12 sites in 2005 and 2006 on more than 135 georeferenced plants per site. Variograms and principal coordinates of neighbour matrices (PCNM) were used to detect significant spatial structures. Variograms indicated a spatially random distribution of aphid populations in a majority (84%) of fields-weeks. For the variograms with a defined structure, the variance between pairs of observations generally increased rapidly with the distance between plants up to a distance where it stabilized, a pattern adequately fitted by spherical models. Structured spatial distributions were more prevalent in 2005 than in 2006, especially at the end of the season. In 2006, PCNM analysis was more sensitive in detecting spatial trends than were variograms. PCNM analysis revealed significant patterns across a broad range of scales, with dominant periods averaging 22.6 and 47.1 m for the short and long transects, respectively. Sampling plants along a 100 m long transect at about 7.5 m intervals in soybean fields would allow detection of the spatial structures identified in this study.
Effect of horticultural oil on oviposition behaviour and egg survival in the obliquebanded leafroller (Lepidoptera: Tortricidae)
Authors: Wins-Purdy A.H. , Whitehouse C. , Judd G.J.R. , Evenden M.L.
Published: March 2009

The effects of the horticultural oil Purespray Green on oviposition behaviour and egg development in the obliquebanded leafroller, Choristoneura rosaceana (Harris), were investigated through dual-choice and no-choice bioassays and topical applications of oil to developing eggs. A residual 2% (v/v) oil spray on wax-paper and apple-leaf substrates significantly reduced both the number of eggs laid and egg survival in no-choice assays; however, this effect diminished 3 days after treatment. In dual-choice assays, females laid significantly fewer eggs on oil-treated apple leaves than on control leaves, but laid equal numbers of eggs on the oil-treated wax paper and the untreated wax-paper controls. Topical application of oil caused significant dose-dependent mortality of both newly laid eggs and eggs just before hatch, and these two egg stages were equally susceptible to the oil. Topical application of 2% oil caused >99% egg mortality. Our data indicate that gravid female C. rosaceana can assess and reject oil-sprayed surfaces and that the oil can kill eggs through both contact toxicity and suffocation. These characteristics suggest that highly purified horticultural oils like Purespray Green could play a role in an integrated pest management program for this important pest species.
Copper/Iron‐Cocatalyzed Highly Selective Tandem Reactions: Efficient Approaches to Z‐γ‐Alkylidene Lactones
Authors: Li Si , Jia Wei , Jiao Ning
Published: March 2009

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Inexpensive copper/iron‐cocatalyzed, efficient, highly regioselective and stereoselective one‐pot tandem conjugate addition–cyclization–hydrolysis–decarboxylation reactions have been developed, which provide efficient tandem reactions for CC and CO bond formation, and the novel synthetic methods of γ‐alkylidenebutyrolactones.
Palladium‐Catalyzed Three‐Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis‐Fused Bicyclo[4.3.0]nonenes
Authors: Shu Wei , Jia Guochen , Ma Shengming
Published: March 2009

Aus 3 mach 1: Die Titelreaktion liefert cis‐anellierte Bicyclo[4.3.0]nonene aus leicht verfügbaren 1,5‐Bisallenen sowie strukturell unterschiedlichen Propargylcarbonaten und Arylboronsäuren (siehe Schema; X=NTs, C(E1)2 mit E1=CO2Bn, SO2Ph; dba=trans,trans‐Dibenzylidenaceton). Der postulierte Mechanismus umfasst eine sequenzielle oxidative Addition, drei Carbopalladierungen in zwei unterschiedlichen Varianten sowie eine Suzuki‐Kupplung.

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Iron‐Mediated Cleavage of CC Bonds in Vicinal Tricarbonyl Compounds in Water
Authors: Mecinović Jasmin , Hamed Refaat B. , Schofield Christopher J.
Published: March 2009

Three of a kind: Vicinal tricarbonyl compounds undergo CC cleavage mediated by ferric ions (see scheme). The observed cleavage of ninhydrin and dehydroascorbic acid has relevance for amino acid detection and the metabolism of vitamin C.

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C(aryl)O Activation of Aryl Carboxylates in Nickel‐Catalyzed Biaryl Syntheses
Authors: Gooßen Lukas J. , Gooßen Käthe , Stanciu Corneliu
Published: March 2009

Crucial breakthroughs in the activation of the C(aryl)O bond of phenol derivatives were achieved almost simultaneously by two research groups (see scheme; Cy=cyclohexyl). Garg et al. coupled a range of aryl pivalates with arylboronic acids to give unsymmetrical biaryls. Shi et al. achieved this through C(aryl)O activation of aryl carboxylates; the best results for the coupling of aryl boroxines were again obtained with aryl pivalates.

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Immunoregulatory effects of HIV‐1 Nef protein
Authors: Quaranta Maria Giovanna , Mattioli Benedetta , Giordani Luciana , Viora Marina
Published: March 2009

During HIV infection, the perturbation of the adaptive and innate immune responses contributes to the progressive immunosuppression leading to an increased susceptibility to opportunistic infections and neoplastic diseases. Several impairments observed in HIV‐infected patients include a gradual loss of CD4+ T cells, CD8+ T cell dysfunction, and a decreased number and function of natural killer (NK) cells. Moreover, a functional impairment and variation in the number of DC and B cells were observed during HIV infection. HIV‐1 codes for proteins, including the accessory Nef proteins, that interacting with immune cells may contribute to AIDS pathogenesis. Here, we review the recent progress on the immunomodulatory effect of the accessory Nef protein and its role in the pathogenesis of HIV‐1 infection. © 2009 International Union of Biochemistry and Molecular Biology, Inc.
Hippocampal, retrosplenial, and prefrontal hypoactivity in a model of diencephalic amnesia: Evidence towards an interdependent subcortical‐cortical memory network
Authors: Vann Seralynne D. , Albasser Mathieu M.
Published: March 2009

The medial diencephalon is vital for memory, but it is not known why. The present study tested between the predictions of current hypotheses as to why this region is critical for memory. Lesions were made in the rat mammillothalamic tract, the only diencephalic structure consistently associated with amnesia in humans after ischemia. Decreased activity, as measured by immediate‐early gene expression (c‐fos), was found in three key sites associated with memory function: the hippocampus, the prefrontal cortex, and the retrosplenial cortex. The specificity of these changes was confirmed by the qualitatively different patterns of immediately‐early gene changes seen after amygdala lesions, e.g., hypoactivity in the hippocampus and retrosplenial cortex following mammillothalamic tract lesions but not following amygdala lesions. The mammillothalamic lesion results unify substrates linked to diencephalic and temporal lobe amnesia, and thereby support a new account of diencephalic amnesia that emphasizes multiple dysfunctions across hippocampal, retrosplenial, and prefrontal areas. This account suggests a role for the mammillary bodies that is independent of their hippocampal inputs. © 2009 Wiley‐Liss, Inc.
The synthesis of N‐[2‐(D‐glucos‐3‐O‐yl)propionyl]‐l‐alanine and N‐[(d‐glucos‐3‐O‐yl)acetyl]‐l‐alanine
Authors: Chikashita Hidenori , Ouchi Tatsuro
Published: March 2009

N‐[2‐(D‐Glucos‐3‐O‐yl)propionyl]‐L‐alanine (7a) was synthesized, which has a glucose residue instead of N‐acetylglucosamine residue in the muramyl peptide. N‐[(D‐Glucos‐3‐O‐yl)acetyl]‐L‐alanine (7b) was also synthesized as a glycolyl analog of 7a in order to determine the relationship between the structure of propionyl moiety in the carbohydrate analog (7a) and the adjuvant activity. These simple analogs are compounds prepared for the purpose of introduction into a synthetic polymer with the view of producing polymeric drugs.
Syntheses with nitriles. 62. 3,5‐Dicyanopyridine derivatives by vilsmeier formylation of malononitrile and tetracyanopropenides
Authors: Mittelbach Martin , Junek Hans
Published: March 2009

Reaction of malononitrile with dimethylformamide and phosphorus oxychloride gave (dimethylamino‐methylene)malononitrile (1), 4‐chloro‐7‐methyl‐5,7‐diaza‐1,3,5‐octatriene‐1,1,3‐tricarbonitrile (3a) and the pyridine 2. Compounds 3a and 3b as well as the triaza‐derivative 3c may also be obtained by treatment of tetracyanopropenides 4a‐c with dimethylformamide and phosphorus oxychloride. Ring closures were achieved by heating 3 under alkaline or acidic conditions. Substitution of chlorine in 3a with aromatic amines provided 1‐aryl‐1,2‐dihydro‐2‐imino‐3,5‐pyridinedicarbonitriles 7. Hydrolysis of 7 gave the 2‐oxo‐derivatives 8.
Ring cleavage reactions of 3‐ and 5‐non‐substituted isoxazoles
Authors: Alberola A. , González A. M. , Guerra D. , Pulido F. J.
Published: March 2009

5‐Methylisoxazoles with electron‐accepting groups at C‐4 (1a‐c) and 2,3‐dimethylisoxazolium iodide (II) undergo ring cleavage when treated with organic bases. The nature of the open chain products which were obtained (stable enolates, β‐diketones, esters) depends on the group at C‐4 and the strength of the base. In some of these processes aromatic aldehydes were used in order to determine the competition between the condensation and the cleavage reaction. The mechanism of the nucleophilic ring cleavage of II is also shown.
The utilization of chemical shift and spin‐lattice (T1) relaxation time data for the discrimination of isomeric indenoisoxazoles
Authors: Womack Charles H. , Gampe Robert T. , Lemke B. Kaye , Sawhney Kailash N. , Lemke Thomas L. , Martin Gary E.
Published: March 2009

Treatment of 2‐pivaloyl‐1,3‐indandione with hydroxylamine leads to the formation of a pair of isomeric indenoisoxazoles, the product formed dependent upon the cyclization conditions. Under acidic conditions, 8‐t‐butylindeno[1,2‐c]isoxazol‐7‐one (5) is formed while under neutral or basic conditions, an oxime, 2, is generated which may then be cyclized under acidic conditions to give 3‐t‐butylindeno[1,2‐c]isoxazol‐4‐one (4). Although these isomeric indenoisoxazoles may be discriminated by chemical means, we were interested in developing an unequivocal method for distinguishing these and potentially other isomeric pairs by spectroscopic means. A 13C‐nmr based method for the discrimination of these isomers which is based on the utilization of chemical shift arguments and spin‐lattice relaxation data is thus presented.
Synthesis of heterocyclic compounds. XXIV. Synthesis of pyridines from β‐substituted α‐phenylacrylonitriles
Authors: Fuentes L. , Vaquero J. J. , Soto J. L.
Published: March 2009

The reaction of malononitrile with α‐phenylcinnamonitriles in ethanolic sodium ethanethiolate is studied as a convenient route to 2‐amino‐4‐aryl‐5‐cyano‐6‐ethylthio‐3‐phenyl‐3,4‐dihydropyridines (5) and the corresponding pyridines 6. From the study of the structure of 5a (Ar = Ph) we can conclude that this cyclization reaction proceeds via a site‐selective addition of the ethanethiolate to the cyano group i of the 1,3‐tricarbonitrile (2).
Carbon‐13 chemical shifts in some 1‐substituted 5‐imino‐3‐phenyl‐4‐thioxo‐2‐imidazolidinones and related compounds
Authors: Litchman William M.
Published: March 2009

The cmr spectra of the title compounds have been obtained and the resonances assigned by classical means. Coupling of the imino proton to C‐5 is observed to be smaller than that to C‐4. A very large downfield shift due to substitution of a carbonyl sulfur at C‐4 is observed. The nmr assignments are shown to be self‐consistent throughout the series.
Syntheses of 10‐Oxo‐10H‐pyrido[1,2‐a]thieno[3,4‐d]pyrimidines and 10‐Oxo‐10H‐pyrido[1,2‐a]thieno[3,2‐d]pyrimidines from methyl tetrahydro‐4‐oxo‐3‐thiophenecarboxylate and methyl tetrahydro‐3‐oxo‐2‐thiophenecarboxylate, respectively
Authors: Connor David T. , Sorenson Roderick J. , Tinney Francis J. , Cetenko Wiaczeslaw A. , Kerbleski Joseph J.
Published: March 2009

A general synthesis of 10‐Oxo‐10H‐pyrido[1,2‐a]thieno[3,4‐d]pyrimidines and 10‐Oxo‐10H‐pyrido[1,2‐a]‐thieno[3,2‐d]pyrimidines is described. Methyl tetrahydro‐4‐oxo‐3‐thiophenecarboxylate (13) was condensed with 6‐aminonicotinic acid (18) to give 3,10‐dihydro‐10‐oxo‐1H‐pyrido[1,2‐a]thieno[3,4‐d]pyrimidine‐7‐carboxylic acid (19). Treatment of 19 successively with chlorotrimethylsilane, N‐chlorosuccinimide and water gave 10‐oxo‐10H‐pyrido[1,2‐a]thieno[3,4‐d]pyrimidine‐7‐carboxylic acid (17). Methyl tetrahydro‐3‐oxo‐2‐thiophenecarboxylate (21) was converted to 10‐oxo‐10H‐pyrido[1,2‐a]thieno[3,2‐d]pyrimidine‐7‐carboxylic acid (25) by an analogous route.
Photochemical and chemical behaviour of 2,5‐hydroperoxyhydroxy‐2,5‐dihydrofurans
Authors: Graziano M. L. , Carli B.
Published: March 2009

From hydroxyhydroperoxides II and III a new bicyclic system, namely the 5,6‐dioxabicyclo[2.1.1]hexane VII is obtained by photolysis or by protic acids. Epimer epoxides IV and XI are obtained on reaction with triethylamine.
Mass spectral fragmentations of 6‐aryl‐5,6,7,8‐tetrahydro‐4H‐1,3,2,6‐dioxathiazocine 2‐Oxides
Authors: Nishiyama Tomihiro , Nakai Yasushi , Kushiyama Masataka , Ikemoto Etsuo , Yamada Fukiko
Published: March 2009

The mass spectral fragmentation of 4‐, 5‐, and 4,8‐disubstituted derivatives of 6‐aryl‐5,6,7,8‐tetrahydro‐4H‐1,3,2,6‐dioxathiazocine 2‐oxides is reported.
Reaction of sulfene with heterocyclic N,N‐disubstituted α‐aminomethyleneketones. VIII. Synthesis of furo[2,3‐h]‐1,2‐benzoxathiin derivatives
Authors: Mosti Luisa , Schenone Pietro , Menozzi Giulia , Romussi Giovanni , Baccichetti Francarosa
Published: March 2009

Cycloaddition of sulfene to N,N‐disubstituted (E)5‐aminomethylene‐6,7‐dihydrobenzo[b]furan‐4(5H)ones I gave, only in the case of aliphatic N‐substitution and generally in satisfactory yields, N,N‐disubstituted 4‐amino‐3,4,5,6‐tetrahydrofuro[2,3‐h]‐1,2‐benzoxathiin 2,2‐dioxides II, which are derivatives of the new heterocyclic system furo[2,3‐h]‐1,2‐benzoxathiin. The 4‐dimethylamino and 4‐piperidino cycloadducts IIa,e were dehydrogenated with DDQ to the corresponding 4‐dialkylamino‐3,4‐dihydrofuro[2,3‐h]‐1,2‐benzoxathiin 2,2‐dioxides IIIa,e in low yield. Compounds IIIa,e were tested for photobiological activity and found to be inactive.
Synthesis of 2‐amino‐6‐chloro‐ and 2,6‐diammopunne 3‐oxides
Authors: Scheinfeld Israel , Parham James C. , Brown George Bosworth
Published: March 2009

N‐Oxidation of 2‐amino‐6‐chloropurine to the 3‐oxide provided a convenient intermediate for the synthesis of 2‐amino‐6‐substituted purine 3‐oxides, including the previously unavailable 2,6‐diaminopurine 3‐oxide. Thiation of the 6‐halogen was accompanied by reduction of the N‐oxide. The properties of the 1‐ and 3‐oxides of 2,6‐diaminopurine are compared.
Polycondensed nitrogen heterocycles. XXII. A new synthesis of 5,6‐dihydro‐7H‐pyrazolo[1,5‐d][1,4]benzodiazepin‐6‐ones
Authors: Dattolo G. , Cirrincione G. , Almerico A. M. , D'Asdia I. , Aiello E.
Published: March 2009

A new synthesis of 2‐methyl‐9‐R'‐10‐R‐5,6‐dihydro‐7H‐pyrazolo[1,5‐d][1,4]benzodiazepin‐6‐ones (4a‐c) is deserved. Reaction of ethyl hydrazinoacetate hydrochloride with 1,3‐diketones 1a‐c gave both 3‐methyl‐5‐(4R'‐5‐R‐2‐nitrophenyl)pyrazol‐1‐yl‐acetate acids (2a‐c) and the corresponding ethyl esters 3a‐c. Reduction with the appropiate reducing agent of compounds 2a‐c and 3a‐c directly gave the title compounds. Compound 4a showed insecticidal properties against the house fly.
Novel reactions of carbon suboxide. Synthesis of 1,5‐benzodioxepins, 1,5‐benzoxathiepins and 1,5‐benzoxazepins
Authors: Bonsignore Leonardo , Loy Giuseppe , Secci Mario , Cabiddu Salvatore
Published: March 2009

The preparation of 1,5‐benzodioxepins, 1,5‐benzoxathiepins and 1,5‐benzoxazepins derivatives is described here. The structure of the products has been determined by elemental analysis and spectroscopic data.
One‐pot synthesis of furano‐ and thieno[3,4‐d]thiepins via bis‐wittig reactions
Authors: Nicolaides D. N. , Tsakalidou E. C. , Hatziantoniou C. T.
Published: March 2009

Bis‐Wittig reactions of dicarbaldehydes 3a‐c, 6 with ylid 2 gave thiepins 4a‐c and 7, respectively. In contrast to the considerable stability of compounds 4a‐c, thiepin 7 was desulfurized to benzo[6]thiophene before its isolation.
Synthesis of steroidal lactam indoxyl
Authors: Catsoulacos P.
Published: March 2009

17‐Ketosteroids condense with o‐nitrobenzaldehyde to yield steroidal indoxyls (1).
Pyrimidines. 20. Novel reactions of 5‐cyano‐1,3‐dimethyluracil. A simple synthesis of pyrido[2,3‐d]pyrimidines
Authors: Su Tsann‐Long , Watanabe Kyoichi A.
Published: March 2009

A reaction of 5‐cyano‐1,3‐dimethyluracil (1, R = CN) with acetone in base afforded 1,3,7‐trimethylpyrido‐[2,3‐d]pyrimidine‐2,4(1H,3H)dione (9a) in a moderate yield. From a reaction mixture of 1 (R = CN) with butanone, 1,3,6,7‐tetramethyl‐ and 7‐ethyl‐1,3‐dimethylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐dione (9b and 9c, respectively) were isolated in low yields. When ethyl cyanoacetate or malononitrile was used in place of the ketone in the above reaction, 7‐amino‐6‐ethoxycarbonyl‐ and 7‐amino‐6‐cyano‐1,3‐dimethylpyrido[2,3‐d]‐pyrimidine‐2,4(1H,3H)‐dione (14a and 14b, respectively) were obtained in quantitative yields. A plausible mechanism for the formation of bicyclic compounds is discussed.
Aminopyrazoles. III . Novel “one‐flask” preparation of 1‐phenylpyrazol‐3‐amine
Authors: Ege Günter , Franz Hermann
Published: March 2009

2‐Chloroacrylonitrile (1a), 2,3‐dichloropropanenitrile (1b), 2,3‐dibromopropanenitrile (1c) or 3‐chloro‐acrylonitrile (1d) react with phenylhydrazine (2) in the presence of potassium t‐butoxide with the formation of 1‐phenylpyrazol‐3‐amine (3) free of the 5‐amino isomer.
Homolytic alkylation of chromones in micellar solution
Authors: Engbersen J. F. J. , Koudijs A. , Van Plas H. C. Der
Published: March 2009

Treatment of an aqueous solution of chromone, the detergent sodium dodecylbenzenesulfonate, silver nitrate and an alkanoic acid, with ammonium peroxydisulfate gives 2‐R‐chromone [R = i‐C3H7 (47%), R = t‐C4H9 (65%) and R = 1‐adamantyl (78%)]. In addition 2‐R‐4‐chromanone [R = i‐C3H7 (40%), R = t‐C4H9 (5%) and R‐1‐adamantyl (10%)] is formed. It is proposed that the reaction involves as intermediate the relatively stable 2‐R‐4‐chromanon‐3‐yl radical and that the detergent has a micellar catalytic activity on the free radical alkylation process.
Preparation and reactions of 3,4‐dihydro‐2H‐pyran‐2‐ones
Authors: El‐Kholy Ibrahim El‐Sayed , Mishrikey Morcos Michael , Abdoul‐Ela Salah Loutfi
Published: March 2009

The Michael reaction of ethyl cinnamates with deoxybenzoin gave ethyl 3,4,5‐triaryl‐5‐oxopentanoates which were hydrolysed to the corresponding acids. The latter could be cyclized to the respective 3,4‐dihydro‐2H‐pyran‐2‐ones which underwent ring opening with several nucleophiles to the corresponding acid derivatives. However, their reaction with ammonium acetate led to the formation of 3,4‐dihydro‐2‐pyridones. The 3,4‐dihydro‐2‐pyrones and pyridones were dehydrogenated to the corresponding 2‐pyrones and 2‐pyridones by fusion with sulfur.
Action of 1,2‐diamines and o‐aminophenols on 1‐alkyl‐3‐carboxyindole‐2‐acetic acid anhydrides. Preparation of new ring systems
Authors: Abdel‐Fattah A. M. , Hussain S. M. , El‐Reedy A. M.
Published: March 2009

1‐Alkyl‐3‐carboxyindole‐2‐acetic acid anhydrides (I) react with ethylenediamine and with o‐phenylenediamine to give directly 10‐alkylimidazo[3,2:1′,2′]pyrido[4,5‐b]indol‐5(1H)‐ones (II) and 5,6‐dihydro‐5‐alkyl‐13H‐indolo[2′,3′:4,5]pyrido[1,2‐a]benzimidazol‐13‐one (V), respectively. However, anhydrides I react with o‐aminophenol and with o‐aminothiophenol to give carboxyindole‐acetanilide derivatives IX, which can be cyclised to indolo[2′,3′:4,5]pyrido[2,1‐b]benzoxazolone and indolo[2′,3′:4,5]pyrido[2,1‐b]benzthiazolone (XI). Some derivatives of II and V were prepared to help in elucidating the structures.
2,2′‐Diindolylmethane. VI (1). NMR‐spektroskopische untersuchungen an chiralen und achiralen 2,2′‐diindolylmethanen mit tryptophanester‐strukturelement
Authors: Pindur Ulf
Published: March 2009

The symmetric properties of some new 2,2′‐diindolylmethanes with chiral centers in the sidechains were investigated on theNMRtime scale. Shift experiments of the chiral 2,2′‐diindolylmethanediesters1ain the presence of 3,3,3‐trifluor‐2‐methoxy‐2‐phenylpropanoic acid were discussed.
Synthesis and transformations of (±)‐trans‐4aβ(H), saα(H)‐octahydro‐4α,7β‐dimethyl‐2H‐1‐benzopyran‐2‐one
Authors: Sanghvi Y. S. , Rao A. S.
Published: March 2009

Hydrogenation of 4,7‐dimethylcoumarin (1) in alkaline medium has been shown to furnish a mixture of (±)‐trans‐4aβ(H),8aα(H)‐octahydro‐4α,7β‐dimethyl‐2H‐1‐benzopyran‐2‐one (2), (±)‐trans‐4aβ(H),8aα(H)‐octahydro‐4α,7α‐dimethyl‐2H‐1‐benzopyran‐2‐one (3) and (±)‐cis‐4aα(H),8aα(H)‐octahydro‐4α,7α‐dimethyl‐2H‐1‐benzopyran‐2‐one (4) in 40:25:35:ratio, respectively. The stereochemistry of the major hydrogenation product 2, has been established by transforming it to p‐menthane derivatives e.g. (±)‐2 (R)‐[2′(R)hydroxy‐4′(R) methylcyclohex‐(1′S)‐yl]propan‐1‐ol (20) and (±)‐trans‐3α,6β‐dimethyl‐3aβ(H),7aα(H)‐octahydrobenzofuran (12). Starting from a mixture of lactones 2, 3 and 4, lactone 3 has been obtained in pure state employing a sequence of reactions.
Studies on the synthesis of heterocyclic compounds. Part IX. Action of N,N‐dimethylformamide dimethylacetal on some oximino‐β‐dicarbonyl compounds
Authors: Plescia Salvatore , Daidone Giuseppe , Sprio Vincenzo
Published: March 2009

3‐Oximino‐2,4‐pentanedione (1) and ethyl 2‐oximino‐3‐oxobutanoate (6) reacted with N,N‐dimethylformamide dimethylacetal (DFDA) to give 1,7‐bisdimethylamino‐3,5‐dioxo‐4‐methoximinohepta‐1,6‐diene (4) and ethyl 5‐dimethylamino‐2‐methoximino‐3‐oxo‐4‐pentenoate (8), respectively. When compounds 4 and 8 were treated with hydrazine hydrate, they gave O‐methyldipyrazol‐3(5)‐ylketoxime (5) and ethyl 2‐methoximino‐3(5)‐pyrazolylethanoate (9) together with its corresponding hydrazide 10, respectively. Upon action of DFDA on 3‐oximino‐2,4‐pentanedione (1) at ‐20° an explosive crystalline product was obtained. On the other hand, the reaction of 3‐acetoximino‐2,4‐pentanedione (11) with DFDA at ‐20° afforded a product which in ethanol solution, spontaneously deacetylated to give 1‐dimethylamino‐3,5‐dioxo‐4‐oximinohexa‐1‐ene (13). The structures of all the new compounds were assigned on the basis of satisfactory analytical and spectroscopic data.
Syntheses and transformations of some 1,2,4‐oxadiazolylpyrazines
Authors: Kočevar M. , Stanovnik B. , Tišler M.
Published: March 2009

Cyanopyrazines with an ortho‐ammo, oxo and other groups are transformed into the corresponding amidoximes. From these the corresponding 1,2,4‐oxadiazolyl derivatives can be prepared and interconversions to the corresponding pteridine 3‐oxides are described.
Synthesis and preliminary in vitro metabolic studies on N,N‐dimethyl‐N′‐2‐imidazolyl‐N′‐benzyl‐1,2‐ethanediamine, an analog of the carcinogenic antihistamine methapyrilene
Authors: Compernolle F. , Castagnoli N.
Published: March 2009

This paper describes the synthesis and preliminary metabolic studies on N,N‐dimethyl‐N′‐2‐imidazolyl‐N′‐benzyl‐1,2‐ethanediamine (compound 12), an imidazole analog of the carcinogenic antihistamine methapyrilene. The 2‐aminoimidazole starting material is carried through a five‐step reaction sequence which involves introduction of the benzyl and dimethylaminoethyl side chains via sequential acylation of the 2‐amino group and reduction of each intermediate amide. Metabolic studies on compound 12 and a d2‐analog were performed with rabbit liver microsomes. Chemical ionization mass spectral analysis indicates the presence of metabolites formed by N‐demethylation and imidazole C‐oxidation. In addition, a seven membered ring metabolite has been identified which apparently is formed by intramolecular cyclization of an intermediate methylene iminium ion.
Activated nitriles in heterocyclic synthesis. A novel synthesis of 1,2,4‐tnazol‐3‐oyl nitriles
Authors: Nada Afaf , Elfahham Hassan Attia , Mohamed Nadia Ragab , Elnagdi Mohamed Hilmy
Published: March 2009

Synthesis of 1,2,4‐triazoloyl nitriles via reaction of 4‐phenylhydrazono‐2‐phenyl‐2‐oxazolin‐5‐one and 4‐phenylhydrazono‐2‐ethoxy‐2‐thiazolin‐5‐one with active methylene nitriles was accomplished. Some of the chemical properties of the nitriles obtained are reported.
Synthesis of 1‐benzylideneisoquinoline‐3,4‐diones
Authors: Castedo Luis , Estévez Ramón J. , Saá José M. , Suau Rafael
Published: March 2009

The synthesis of 1‐benzylideneisoquinoline‐3,4‐diones 7 is described for the first time. This has been achieved through two new methods based on the controlled oxidation of the isoquinoline nucleus of the corresponding 1‐benzylisoquinolin‐3‐ones.
Non‐Steroidal antiinflammatory agents. 1. A novel synthesis of 1‐methyl‐5‐p‐tolylpyrrole‐2‐acetic acid (tolmetin)
Authors: Artico Marino , Corelli Federico , Massa Silvio , Stefancich Giorgio
Published: March 2009

A four‐step preparation of 1‐methyl‐5‐p‐totylpyrrole‐2‐acetic acid (Tolmetin) is reported starting from 1‐methyl‐2‐p‐tolylpyrrole. Formylation of this compound followed by condensation with methyl(methylthio)‐methyl sulfoxide furnished 1‐(methylsulfinyl)‐1‐methylthio‐2‐(1‐methyl‐5‐p‐tolyl‐2‐pyrrolyl)ethylene. Pummerer rearrangement of the latter compound gave ethyl 1‐methyl‐5‐p‐tolylpyrrole‐2‐acetate, which was hydrolyzed in alkaline medium to afford Tolmetin.
Mass spectra of some (Z)‐α‐Phenyl‐β‐(2‐thienyl)acrylonitriles
Authors: Carbone D. , Fisichella S. , Occhipinti S. , Scarlata G.
Published: March 2009

The mass spectra of some (Z)α‐(4‐R′‐phenyl)‐β‐(2‐thienyl‐5‐R)acrylonitriles (R = H, CH3, Br; R′ = H, CH3O, CH3, Cl, NO2) at 70 eV are reported. Mass spectra exhibit pronounced molecular ions. The compound's where R = H, and CH3 are characterized by the occurrence of a strong [M ‐ H]+ peak. Moreover, in all the compounds a m/z 177 peak occurs. In the compounds where R = H, [M ‐ HS]* and [M ‐ CHS]* ions are present except the nitroderivatives. Where R = CH3, [M ‐ HS]+ ion occurs.
The synthesis and hydrolysis of N‐benzyl‐S‐methylisothiazolidinium salts
Authors: Swank Darrel W. , Lambeth David O.
Published: March 2009

A series of N‐benzyl‐S‐methylisothiazolidinium salts were obtained by iodinic oxidation of the corresponding N‐benzyl‐3‐methylthiopropylamines at neutral pH followed by their isolation as the chloride salts. The parent N‐benzyl‐3‐methylthiopropylamines were prepared by reacting substituted benzaldehydes with 3‐methylthiopropylamine and sodium cyanoborohydride. Acid hydrolysis of the isothiazolidinium salts resulted in their quantitative conversion to the corresponding N‐benzyl‐3‐methylsulfenylpropylamines. Although methylsulfenylpropylamine formation also predominated in alkaline solution, a significant fraction was converted to the parent benzaldehyde and presumably, 3‐methylthiopropylamine. The latter conversion is believed to involve opening of the isothiazolidine ring via an elimination reaction followed by hydrolysis of the resulting Schiff's base.
Studies on ketene and its derivatives. CXI . Photoreaction of diketene with 2(1H)‐quinolone derivatives
Authors: Chiba Takuo , Okada Minora , Kato Tetsuzo
Published: March 2009

Photoreaction of diketene with 4‐methyl‐2(1H)‐quinolone and 1,4‐dimethyl‐2(1H)‐quinolone gave 2R*,2aR*,SbR*‐ and 2R*,2aS*8bS*‐8b‐methyl‐3‐oxo‐1,2,2a,3,4,8b‐hexahydrocyclobuta[c]quinoline‐2‐spiro‐2′‐(oxetan)‐4′‐one (6a and 6b), and their 4‐methyl derivatives 7a and 7b, respectively. Thermolysis of compounds 6 and 7 afforded 2aR*,8bS*‐8b‐methyl‐2‐methylene‐3‐oxo‐1,2,2a,3,4,8b‐hexahydrocyclobuta[c]quinoline (8) and its 4‐methyl derivatives 9, respectively. Similarly, photolysis of diketene and 4‐acetoxy‐2(1H)‐quinolone gave 1R*,2aS*,8bS*‐ and 1R*,2aR*,8bR*‐8b‐acetoxy‐3‐oxo‐1,2,2a,3,4,8b‐hexahydrocyclobuta[c]‐quinoline (11a and 11b). Alcoholysis of compounds 11a and 11b with hydrogen chloride in methanol gave 1‐hydroxy‐1‐(methoxycarbonyl)methylcyclobuta[c]quinoline derivative 12 and 13 which were transformed to 4‐acetyl‐3‐methyl‐2(1H)‐quinolone (15) by further alcoholysis. Photoreaction of diketene with 2(1H)‐quinolone derivatives gave the corresponding cyclobuta[c]quinoline spirooxetanone derivatives 18 and 23, which, by thermolysis, were transformed to 2‐methylenecyclobuta[c]quinoline 23 and 25, respectively.
Reactions of N‐aminophthalimide with electrophiles. II. Preparation and properties of araldehyde hydrazones
Authors: Hearn Michael J. , Lucero Elena R.
Published: March 2009

N‐Aminophthalimide (I) reacted with a variety of aromatic aldehydes to give the related arylideneaminophthalimides (III‐X), although typical ketones such as acetone and benzophenone did not under the specific conditions employed. Catalytic reduction of benzylideneaminophthalimide (III) led to N‐benzylaminophthalimide (XI), a stable acid‐free precursor of benzylhydrazine.
Opposite CD curves in chromophoric derivatives of 3‐substituted 5‐and 6‐membered cyclic amines
Authors: Bettoni Giancarlo , Cellucci Carla
Published: March 2009

Absolute configuration was assigned to 3‐isopropylpyrrolidine by chemical correlation with R‐3‐isopropylsuccinic acid. The comparison between CD curves of 3‐substituted piperidines, morpholines and pyrrolidine having the same chirality shows that the chiroptical properties of these five and six‐membered cyclic amine derivatives are opposite.
Synthesis of the p‐nitrophenyl ester of acridine‐2‐acetic acid
Authors: Kauffman Joel M. , Taraporewala Irach B.
Published: March 2009

The title compound, 8, which is expected to serve as a fluorescent substrate for α‐chymotrypsin, was prepared by esterification of acridine‐2‐acetic acid, 4, whose synthesis was achieved by two routes. One began with 4‐aminophenylacetic acid and proceeded through the acridanone‐2‐acetic acid, 3, in 49% yield overall. The other began with 4‐aminoacetophenone and proceeded through 2‐acetylacridanone, 6, in 3% yield overall.
Chemistry of the phenoxathiins and isosterically related heterocycles. XXV . Synthesis of 1,6‐diazathianthrene from 3‐mercaptopyridin‐2(1H)‐thione via a novel dehydrothiolation reaction in the presence of triethylamine
Authors: Puig‐Torres Salvador , Womack Charles H. , Martin Gary E. , Smith Keith
Published: March 2009

The generation of the dianion of 3‐mercaptopyridin‐2(1H)‐thione with triethylamine in N,N‐dimethylform‐amide followed by reaction in the presence of 2‐chloronitrobenzene fails to give 1‐azathianthrene which is formed in good yield when sodium hydride was employed as the base. The principle product isolated from the reaction was instead 1,6‐diazathianthrene. Mechanistic considerations are discussed.
Synthesis of 5,8‐dihydro‐5‐oxo‐2‐(3‐ or 4‐pyridinyl)‐pyrido[2,3‐d]pyrimidine‐6‐carboxylic acids and the reinvestigation of the thermal cyclization of diethyl (2‐hydroxy‐4‐pyrimidinyl)amino‐methylenemalonate
Authors: Singh Baldev , Lesher George Y.
Published: March 2009

Diethyl [2‐(3‐ or 4‐pyridinyl)‐4‐pyrimidinyl]aminomethylenemalonates 5 prepared by the reaction between 2‐(3‐ or 4‐pyridinyl)‐4‐pyrimidinamines 3 and diethyl ethoxymethylenemalonate (4) were thermally cyclized to afford ethyl 5,8‐dihydro‐5‐oxo‐2‐(3‐ or 4‐pyridinyl)pyrido[2,3‐d]pyrimidine‐6‐carboxylates 6. The later were alkylated with ethyl iodide and then saponified to give 5,8‐dihydro‐8‐ethyl‐5‐oxo‐2‐(3‐ or 4‐pyridinyl)pyrido‐[2,3‐d]pyrimidine‐6‐carboxylic acids 2. Thermal cyclization of diethyl (2‐hydroxy‐4‐pyrimidinyl)amino‐methylenemalonate (8) gave ethyl 1,6‐dihydro‐4,6‐dioxo‐4H‐pyrimido[1,6‐a]pyrimidine‐3‐carboxylate (10) instead of ethyl 5,8‐dihydro‐2‐hydroxy‐5‐oxopyrido[2,3‐d]pyrimidine‐6‐carboxylate (9) as previously claimed.
1,2,4‐Triazines. 5. Regioselective N2‐amination of 3‐methylthio‐1,2,4‐triazin‐5(2H)‐ones. A new efficient synthesis of [1,2,4]triazolo[2,3‐b][1,2,4]triazin‐7(1H)‐one
Authors: Sanemitsu Yuzuru , Nakayama Yoshinori , Shiroshita Masao
Published: March 2009

A regioselective synthesis of 2‐amino‐1,2,4‐triazinones (3a‐b) is reported, by reaction of 3‐methylthio‐1,2,4‐triazinones (1a‐b) with O‐(2,4‐dinitrophenyl)hydroxylamine (2), as an amino transfer agent. A spectroscopic study and an unequivocal synthesis of 2‐amino‐4‐methyl‐6‐phenyl‐1,2,4‐triazinone (8a) has shown the site of amination to be N2 of the 1,2,4,‐triazinone ring. Subsequent reaction of 2‐amino‐1,2,4‐triazinone (3b) with ammonium hydroxide, followed by ring closure with formic acid provided [1,2,4]triazolo[2,3‐b][1,2,4]triazin‐7 (1H)‐one (10).
Action d'organolithiens sur la méthyl‐2 quinoxaline. Etude de la réactivité des adduits
Authors: Mettey Yvette , Vierfond Jean‐Michel , Thai Claude , Miocque Marcel
Published: March 2009

L'action d'organolithiens comme le butyllithium et le phényllithium sur la méthyl‐2 quinoxaline conduit soit à une métallation du méthyle soit à l'addition de l'organolithien sur une (ou sur les deux) liaisons imini‐ques du noyau pyrazinique suivie ou non de métallation du méthyle.L'addition d'eau (réaction A) au mélange réactionnel permet l'isolement de composés stables dihydro‐ou tétrahydroquinoxalines. L'addition d'électrophiles comme l'o‐chlorobenzonitrile (réactionB) ou le benzoate de méthyle (réactionC) livre des produits C ou N condensés à partir des intermédiates lithtés formes. Seul le benzoate de méthyle donne des produits de condensation à l'azote.
Pyrimidines. 6. 6‐trifluoromethyl chloropyrimidines and related compounds
Authors: Gershon Herman , Grefig Anthony T. , Scala Alfred A.
Published: March 2009

A study of the chlorination of 6‐trifluoromethylpyrimidines was made. On sequential treatment of 6‐tri‐fluoromethyluracil (6) with phosphorus oxychloride and phosphorus pentachloride, 2,4‐dichloro‐6‐trifluoro‐methylpyrimidine (7) (25%) and 4‐chloro‐6‐trifluoromethylpyrimidin‐2‐yldichlorophosphate (8) (53%) were obtained. Compound 8 was converted to 7 by treatment with hydrogen chloride in phosphorus oxychloride in 72% yield. In a one‐pot synthesis, 77% of 7 was obtained from 6. The preparation of 2,4,5‐trichloro‐6‐tri‐fluoromethyluracil (16) proceeded similarly. Although the pyrimidinyldichlorophosphate ester has been proposed as the intermediate in converting a pyrimidinol to a chloropyrimidine, these are the first examples of such compounds to be isolated, characterized, and made to yield the ring‐chlorinated pyrimidines.
Hetarylpyrazoles. IV. Synthesis and reactions of 1,5′‐bipyrazoles
Authors: Khan Misbahul Ain , Freitas Antonio Carlos Carreira
Published: March 2009

A number of 1, 5′‐bipyrazoles were obtained from the condensation of pyrazol‐5‐ylhydrazine and 1, 3‐dicarbonyl compounds. Electrophilic substitution reactions of these 1, 5′‐bipyrazoles occur at the four position of the pyrazole ring.
Reactions of the monoxides of 2,6‐disubstituted pyrazines with phosphoryl chloride and acetic anhydride
Authors: Ohta Akihiro , Imazeki Akiko , Itoigawa Yokho , Yamada Hiroko , Suga Chieko , Takagai Chiseko , Sano Hiroko , Watanabe Tokuhiro
Published: March 2009

The monoxides of 2, 6‐dimethyl‐(1), 2, 6‐diphenyl‐(2), and 2‐methyl‐6‐phenylpyrazines (3) were subjected to the reactions with phosphoryl chloride and acetic anhydride. Some reactions of the chloropyrazines and hydroxypyrazines obtained thus were also investigated.
Synthèse de nouvelles amidines bicycliques . Dérivés de la pyrimidine, de la quinazoline et de la diazépine‐1,3
Authors: Langlois Michel , Guilloneau Claude , Van Tri Vo , Jolly Raymond , Maillard Jacques
Published: March 2009

Les auteurs décrivent la synthèse de pyrrolo [1,2‐α]pyridine et quelques homologues contenant un cycle pyridine ou azépine à la place du pyrrole. Ces composès sont prèparès par cylisation d'imiolactames avec des β‐cétoesters, des esters, aldéhydes ou cétones αβ‐insaturés ou du dicétèsne La possibilité d'obtention d' isomères est discutée.
Reactions of halogenoquinolizinium bromides with aniline, isopropylamine and liquid ammonia
Authors: Sanders G. M. , van Dijk M. , van der Plas H. C. , Konijn M. , Stam C. H.
Published: March 2009

The reactions of quinolizinium bromide (QB) and its four monobromo derivatives with aniline, isopropylamine and liquid ammonia have been investigated. With aniline 2‐ and 4‐bromo QB undergo substitution, whereas 1‐ and 3‐bromoQB do not react at all. With liquid ammonia all bromo derivatives and the parent compound react with ring opening. This diversity in the reaction course is explained in terms of the HSAB principle. 2‐BromoQB reacts with isopropylamine under formation of 2‐isopropylaminoQB. Two molecules of isopropylamine are involved in this substitution, as we isolated an intermediate: 1‐isopropylamino‐4(2‐pyridyl)‐3‐isopropyliminio‐1‐butene bromide (13). The structure of the latter compound was confirmed by X‐ray analysis.
A synthesis of 5‐oxo‐1,2,3,4‐tetrahydro[1,4]azepino‐[6,7,1 ‐kl]phenothiazine
Authors: Pinto Angelo C. , Schirch Paulo , Hollins Richard A.
Published: March 2009

A synthesis of a new heterocyclic system (5) is described starting from 1‐carbomethoxyphenothiazine.
A short regiospecific total synthesis of furoventalene, a marine natural benzofuran
Authors: Bergstrom Donald E. , Reddy P. Anantha
Published: March 2009

Synthesis of a naturally occurring irregular isoprenoid benzofuran, furoventalene (3), has been achieved in high yield via the nickel catalyzed coupling of 4‐methyl‐3‐penten‐1‐ylmagnesium bromide (1) with 3‐methyl‐6‐chlorobenzofuran (2).
The synthesis and characterisation of some 2,7‐diazaphenanthrene derivatives
Authors: Gill E. W. , Bracher A. W.
Published: March 2009

2,7‐Diazaphenanthrene was synthesised in moderate yield by the modified Pomeranz‐Fritsch reaction by condensing diethoxyethanal with 1,4‐benzenebismethanamine, followed by ring closure with 20% oleum, and its spectral characteristics recorded. A similar reaction with diethyl 1,4‐benzenebis(3‐aminopropanoate) gave either 2,7‐diaza‐1,8‐dimethylphenanthrene or 2,7‐diaza‐1,8‐phenanthrenebis(methylsulphonic acid), depending on the conditions of the ring closure reaction. The bis methiodides of these compounds were tested for phospholipase A2 inhibitory action but were found to be inactive.
Sur l'orientation de la nitration des nitriles et amides coumariliques Bz‐méthoxylés
Authors: Bachelet Jean‐Pierre , Demerseman Pierre , Royer René
Published: March 2009

Les nitrations directes des carboxamido‐2 ou cyano‐2 Bz‐méthoxy benzofurannes par l'acide nitrique dans l'anhydride acétique donnent toujours deux dérivés nitrés sur l'homocycle, en ortho ou éventuellement en para du méthoxyle, en proportions différentes selon les cas. Les nitro carboxamides et les nitro nitriles méthoxylés obtenus sont déméthylables par le chlorure de pyridinium. Leur hydrolyse en acides correspondants s'effectue sans déméthylation par l'acide sulfurique dilué et, à une exception pre̊s, avec déméthylation simultanée par la soude diluée.
2‐Benzazepines. 7. Synthesis of pyrimido[5,4‐d][2]benzazepines
Authors: Earley James V. , Fryer R. Ian , Gilman Norman W.
Published: March 2009

Two novel syntheses of pyrimido[5,4‐d][2]benzazepines are described. The first synthesis started with 3‐phenylphthalide which in three steps was converted to a functionalized pyrimidine which was cyclized to give the 2‐benzazepine ring system. The second approach used o‐benzoylbenzoic acid methyl ester as the starting material, which in four steps was converted to a functionalized pyrimidine which was cyclized to give a 2‐benzazepine. Pyrimido[5,4‐d][2]benzazepines have been found to have activity in standard central nervous system (CNS) pharmacological tests.
Synthesis of 1‐cyano‐2‐methylisoindole. A new route to isoindoles
Authors: D'Amico John J. , Stults B. Ray , Ruminski Peter G. , Wood Karl V.
Published: March 2009

The reaction of o‐phthaldehyde with potassium cyanide and methylamine hydrochloride afforded 1‐cyano‐2‐methylisoindole (1) in 92% yield. Possible mechanism and supporting nmr, ir, mass spectrum and single X‐ray structure analysis for 1 are discussed. The X‐ray study revealed that the true structure of 1 can best be represented as a resonance hybrid of the canonical forms a, b, c and d.
The reaction of 4‐alkyl‐3‐thiosemicarbazides with β‐haloketones
Authors: Jones Winton D. , Kane John M. , Sill Arthur D.
Published: March 2009

The reactions of 4‐alkyl‐3‐thiosemicarbazides with β‐halophenones and o‐halophenones gave 4,5‐dihydro‐N‐alkyl‐3‐phenyl‐1H‐pyrazole‐1‐carbothioaraides and 3‐phenyl‐1H‐indazoles, respectively.
Pyrimidines from furfural. A convenient synthesis of 5‐bromo‐ and 5‐chloropyrimidine
Authors: Kress Thomas J. , Szymanski Edward
Published: March 2009

A new method for the preparation of 5‐bromo‐ and 5‐chloropyrimidine from furfural has been described.
Effect of metal ions in organic synthesis. Part XXXI. Synthesis of new 3‐carbonyl‐ and 3‐carboxy‐1‐heterocyclaminopyrroles by copper(II) chloride‐catalyzed reaction of heterocyclic azoalkenes
Authors: Attanasi Orazio , Filippone Paolino , Mei Amedeo , Serra‐Zanetti Franco
Published: March 2009

The direct synthesis of a new class of unknown 1‐heterocyclamino‐3‐carbonylpyrroles and 1‐heterocyclamino‐3‐carboxypyrroles by copper(II) chloride‐catalyzed reaction of heterocyclic conjugated azoalkene derivatives with β‐diketones and β‐ketoesters is reported.
Preparation and characterization of 16‐benzoylated tetraaza[14]annulenes
Authors: Sakata Kazunori , Tagami Hidetoshi , Hashimoto Mamoru
Published: March 2009

The condensation reaction between tetraaza[14]annulene (1) and a series of para‐substituted benzoyl chlorides led to the 16‐benzoylated corresponding products in 13–21% yields, but 1 was unreactive with alkyl acid chlorides and easily cleaved in macrocyclic framework. The mass spectra show the presence of molecular ion peaks which support the 16‐benzoylated products. A strong ir band due to the C = N stretching mode of the macrocyclic moiety was observed at 1610 cm−1 and shifted slightly toward higher energy upon benzoylation. An intense ir band which was associated with a C = 0 stretching mode was newly observed at 1640 cm1. The very strong absorption band about 29000 cm−1 was attributed to the π − π* transition and gave a slight shift to higher frequency on benzoylation. All proton signals except for methyl protons exhibit downfield shifts due to the deshielding effect of the substituted benzene ring, but the methyl proton peaks show upfield shifts due to the shielding effect caused by the magnetic anisotropy of the substituted benzene ring. The 13C nmr result is also in accord with that of 1H nmr.
2‐Chloro‐3H‐indol‐3‐one and its reactions with nucleophiles
Authors: Katritzky Alan R. , Fan Wei‐Qiang , Koziol Anna E. , Palenik Gus J.
Published: March 2009

The title compound reacts with N‐ and S‐nucleophiles to form 3‐substituted indol‐2‐ones, but with C‐nucleo‐philes to afford either these or the corresponding 2‐substituted indol‐3‐ones. This dichotomy of behavior is documented and rationalized.
A short and efficient synthesis of grisan
Authors: Kaufman Teodoro S. , Sindelar Robert D.
Published: March 2009

A three‐step synthesis of grisan (spiro[benzofuran‐2(3H)‐1′‐cyclohexane]), using methoxymethoxybenzene and 1‐chloromethylcyclohexene as starting materials, is described.
Bis heterocycles as potential chemotherapeutic agents. X. Synthesis of bis(4‐arylthiosemicarbazido)‐, bis(2‐arylamino‐1,3,4‐thiadiazol‐5‐yl) and bis(4‐aryl‐1,2,4‐triazolin‐3‐thione‐5‐yl)pentanes and related compounds
Authors: Ram Vishnu J. , Mishra Lallan , Pandey N. H. , Kushwaha D. S. , Pieters Luc A. C. , Vlietinck Arnold J.
Published: March 2009

Synthesis of several bis(4‐arylthiosemicarbazido‐ 1, bis(2‐arylamino‐1,3,4‐thiadiazol‐5‐yl)‐ 5 and bis(4‐aryl‐1,2,4‐triazolin‐3‐thione‐5‐yl)‐ 2 pentanes is described. Sulphides 3 and sulphones 4 are also prepared from 2 by alkylation and subsequent oxidation with hydrogen peroxide respectively.