bluuebunny/crossref_metadata_2025_split huggingface dataset:
Unambiguous structure of the compounds in the reaction of L‐tryptophan and 5‐hydroxy‐l‐tryptophan with alkyl isocyanates in acetone
Authors: Garrido Mercedes , López Rodriguez Maria L. , José Morcillo M. , Garcia Virginia Pérez , Monge A. 
Published: March 2009

AbstractOn the basis of X‐ray crystallographic analysis, it is shown that the reaction of L‐tryptophan and 5‐hydroxy‐L‐tryptophan with alkyl isocyanates in acetone affords, in agreement with Claesson's work, 3‐alkylcarbamoyl‐4‐(3‐indolylmethyl)‐1,3‐oxazolidin‐5‐ones 2 and not 2‐[(3‐alkyl‐4,4‐dimethyl‐2‐oxo)‐1,3‐diazetidinyl]‐3‐(3‐indolyl)propionic acids 1 as previously proposed.
Synthesis of new polycyclic systems containing the pyrimido[2,1‐a]phthalazine skeleton
Authors: Santagati Andrea , Santagati Maria , Russo Filippo 
Published: March 2009

AbstractThe synthesis of new polyheterocycles containing the pyrimido[2,1‐a]phthalazine system 5, 6 and 7, obtained by condensation of phthalic anhydride with the appropriate hydrazides 2, 3 and 4, respectively, are reported. It was also synthesized the 14H‐[1]Benzothieno[3′,2′:4,5]pyrimido[2,1‐a][1,2,4]triazolo[4,3‐c]phthalazin‐14‐one (16).
Diels‐alder reactions of cyclohexadienes derived from decarboxylation of photo[4 + 2]cycloadducts between 4,6‐dimethyl‐2‐pyrone and cyclic olefins
Authors: Shimo Tetsuro , Matsuo Kenji , Somekawa Kenichi , Tsuge Otohiko 
Published: March 2009

AbstractLabile photo [4 + 2] adducts between 4,6‐dimethyl‐2‐pyrone and cyclic olefins reacted with second olefins to give cross adducts, and with acetylenes to afford both bis‐adducts and benzene derivatives with the concurrent decarboxylation, respectively. The reaction mechanism of the latter was considered.
Cycloaddition of benzothiete and electron‐deficient nitriles
Authors: Schmidt Michael , Meier Herbert , Saleh Sadiq A. 
Published: March 2009

AbstractThe o‐quinoid 8π electron system 2, generated by thermal ring opening of benzothiete (1), enters regio‐specific [8π + 2π] cycloaddition reactions with electron‐deficient nitriles 3a‐d, yielding the 4H‐1,3‐benzothiazines 4a‐d. A competitive dimerization of 1 leads to 1,5‐dibenzo[b,f]dithiocin (5). Depending on the nitrile further competitive or subsequent reactions (2 + 3b → 7b, 2 + 3d → 4d → 8d) can occur. The cycloadducts 10e and 11e gained from 3e anticipate a primary cleavage of 3e to methylisothiocyanate 9e which reacts at the CN double bond as well as at the CS double bond.
Synthesis and structure of pyrazolo[5,1‐a]isoindol‐8‐ones from Aromatic Ortho Diesters
Authors: Chupp John P. , Leo Gregory C. , Molyneaux John M. 
Published: March 2009

AbstractThe title compounds 2, have now been shown to arise in certain cases from condensation of aromatic ortho‐diesters with ketone, where formerly only indeno[1,2‐c]pyrazol‐4(1H)‐ones 3 have been reported from such reaction. Heretofore 2 was obtained in a less direct fashion from phthalaldehydic acid esters. When hetero‐aromatic diesters were employed, new heterocyclic ring systems as represented by 2a,b,c were prepared for the first time. Structures of 2 have been verified from detailed 1H and 13C nmr studies, while representative intermediates 4–9 in the condensation of diesters to 2 have been isolated and identified.
Synthesis of (±)‐pantolactone and (±)‐dihydro‐4‐ethyl‐3‐hydroxy‐4‐methyl‐2(3H)‐furanone
Authors: Kinoshita Takamasa , Hirano Madoka , Miyake Hiroyuki 
Published: March 2009

AbstractThe title compounds were synthesized from 3‐furoic acid via the Birch reduction.
Influence of the heterocyclic side ring on orientation during nitrations of 1,2‐alkylenedioxy‐annelated benzenes and their mononitro derivatives
Authors: Takakis Ioannis M. , Hadjimihalakis Phaedon M. 
Published: March 2009

AbstractNitration of 1,2‐alkylenedioxybenzenes 1 furnished the respective nitro derivatives 3 and 4 in the relative ratios: 4a:3a/100:trace, 4b:3b/98:2.4, 4c:3c/86:14, 4e:3e/91:9 and 4f:3f/99:1.3. Nitration of 4 gave 5a:6a:8a/0:0:100, 5b:6b:8b/7.7:3.2:89, 5c:6c:8c/23:12:65, 5d:6d:8d/14:74:12, 5e:6e:8e/27:18:55 and 5f:6f:8f/23:7.0:70. Nitration of the isomeric 3 afforded the dinitro products 5, 6 and 7 in the following relative ratios: 5a:6a:7a/92:8:0, 5b:6b:7b/80:20:0, 5c:6c:7c/69:20:1 1, 5d:6d:7d/45:19:36, 5e:6e:7e/37:57:5.9 and 5f:6f:7f/64:36:0. Nitration of 3‐nitro‐1,2‐dimethoxybenzene (9) furnished: 10:11/63:37. Orientation as a function of the heterocyclic ring‐size is discussed.
Diheterocyclic compounds from dithiocarbamates and derivatives thereof. VI. unsymmetrical N1,N4‐Bis(2‐benzazolyl)sulphanilamides
Authors: Meléndez Enrique , Merchán Francisco L. , Merino Pedro , Orduna Jesús , Urchegui Raquel 
Published: March 2009

AbstractThe title compounds 9 are readily synthesized from dithiocarbamic acid derivative 5 by stepwise formation of the heterocyclic rings. Differences in reactivity of dithiocarbamates and dithiocarbonimidates make group protection unnecessary.
The synthesis and chemistry of 5‐carboxy‐8‐mercaptoquinoline hydrochloride monohydrate: An intermediate in the synthesis of novel H+,K+‐ATPase inhibitors
Authors: Zawistoski Michael P. 
Published: March 2009

AbstractThe title compound 3 was prepared in six steps from 5‐nitro‐8‐hydroxyquinoline in 14% overall yield, using a substituted pyrimidine as a protecting group for sulfur. This offers a simple entry into the synthesis of 5‐carboxy‐8‐substituted thioquinolines, useful intermediates for the synthesis of H+,K+‐ATPase inhibitors.
Synthèse de 2‐pyrimidinylphénols et de 2‐pyrazolylphénols
Authors: Sacquet Marie‐Claude , Fargeau‐Bellassoued Marie‐Claude , Graffe Bernadette 
Published: March 2009

AbstractDe nouveaux pyrimidinylphénols 9a‐e et pyrazolylphénols 10a‐e substitués par des groupes aminométhyles sont préparés avec de bons rendements par action respective du carbonate de guanidine et de l'hydrate d'hydrazine sur les 3‐aminométhylchromones 8a‐e. Ces 3‐aminométhylchromones 8a‐e sont aisément obtenues par réaction de Mannich sur la chromone 5. Les rendements en chromone 5 et en aminométhylchromones 8a‐e ont été notablement améliorés.
Quinolone antibacterials. 1. 7‐(2‐substituted‐4‐thiazolyl and thiazolidinyl)quinolones
Authors: Zhang M. Q. , Haemers A. , Vanden Berghe D. , Pattyn S. R. , Bollaert W. , Levshin I. 
Published: March 2009

AbstractA series of 7‐(2‐substituted‐4‐thiazolyl and thiazolidinyl)‐1‐ethyl‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acids and their 6‐fluoro analogues were synthesized. The Hantzsch method was used for the preparation of the thiazolylquinolones. The thiazolidinylquinolones were synthesized by quaternization of the corresponding thiazolyl analogues, followed by reduction of the obtained thiazolium salts with sodium borohydride in aqueous solution. Antibacterial activity was tested in vitro. Most of the compounds were inactive against Gram‐negative bacteria but some of them showed however good activity against Gram‐positive bacteria and mycobacteria. This activity pattern is rarely found among the quinolone antibacterials.
Identification, synthesis and conformational study of a CN(R,S) synthon by‐product: (5R, 10R)‐5,10‐diphenyl‐1,6‐diaza‐3,8‐dioxabicyclo[4.4.1]undecane
Authors: Aitken David J. , Guillaume Dominique , Husson Henri‐Philippe , Chiaroni Angèle , Riche Claude 
Published: March 2009

AbstractThe title compound, containing a new heterocyclic skeleton, was identified by X‐ray crystallography as the product of condensation of (R)‐phenylglycinol with an excess of formaldehyde. The molecule adopts a rigid double twist‐chair conformation in both solid and solution states.
On triazoles XXIV. Synthesis of cycloalka[1,2,4]triazolo[1,5‐a]pyrimidinones
Authors: Reiter József , Berecz Gábor , Pallagi István 
Published: March 2009

AbstractThe uv and nmr spectral data of some 6,7,8,9,10,11‐hexahydrocyclohepta[d][1,2,4]triazolo[1,5‐a]pyrimidin‐5‐one, 5,6,7,8,9,11‐hexahydrocyclohepta[e][1,2,4]triazolo[1,5‐a]pyrimidin‐10‐one, 6,7,8,9,10,11‐hexahydrocycloocta[d][1,2,4]triazolo[1,5‐a]pyrimidin‐5(12H)‐one, 5,6,7,8,9,10‐hexahydrocycloocta[e][1,2,4]triazolo[1,5‐a]‐pyrimidin‐11(12H)‐one, 6,7,8,9,10,11,12,13,14,15‐decahydrocyclododeca[d][1,2,4]triazolo[1,5‐a]pyrimidin‐5(16H)‐one and 5,6,7,8,9,10,11,12,13,14‐decahydrocyclododeca[e][1,2,4]triazolo[1,5‐a]pyrimidin‐15(16H)‐one as well as their N‐benzylated derivatives representing six novel ring systems were compared to prove their structure. The N‐benzylation of the highly insoluble cyclic amides to yield the isomeric N‐benzyl derivatives 3/1, 3/2 and 3/3 distinguished by INAPT was performed through their readily soluble tetrabutylammonium salts.
The synthesis of novel polycyclic heterocyclic ring systems via photocyclization. 4. Benzo[f]thieno[2′,3′:4,5]thieno[2,3‐c]quinoline and Benzo[h]thieno[2′,3′:4,5]thieno[2,3‐c]quinoline and the total assignment of their 1H‐ and 13C‐NMR spectra
Authors: Luo Jiann‐Kuan , Zektzer Andrew S. , Castle Raymond N. 
Published: March 2009

AbstractThe synthesis of two novel polycyclic heterocyclic ring systems via photocyclization are reported. These are benzo[f]thieno[2′,3′:4,5]thieno[2,3‐c]quinoline and benzo[A]thieno‐[2′,3′:4,5]thieno[2,3‐c]quinoline. The total assignment of their 1H‐ and 13C‐nmr spectra was determined by utilizing two‐dimensional nmr spectroscopic methods.
Preparation of diastereomeric 5,8‐methanobenzoxazino[2,1–6]‐ and [2,3–6]‐1,3‐benzoxazin‐4‐ones by reaction of norbornane/ene‐condensed dihydro‐1,3‐oxazines with salicyl chloride
Authors: Stájer Géza , Frimpong‐Manso Samuel , Bernáth Gábor , Sohár Pál 
Published: March 2009

AbstractNorbornane and norbornene‐condensed dihydro‐1,3‐oxazines 1–6 were converted with salicyl chloride to 5,8‐methanobenzoxazino[2,1–6]‐ and ‐[2,3‐b]‐1,3‐benzoxazin‐4‐ones 7–12. The addition takes place to the C  N bond: after acylation, the intermediate is stabilized through cyclization to the aryl‐substituted carbon by hydrogen chloride elimination. Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases. This is the first example of the isolation of diastereomers in such a salicyl chloride reaction. In contrast with earlier findings with reactions of related systems, no addition to the C  C bond could be observed. The steric structures of the compounds were elucidated by ir, 1H‐ and 13C‐nmr spectroscopy.
Synthesis of new 2‐aryl‐3,3a‐dihydro‐4‐oxo‐5H‐pyrazolo‐[1,5‐d][1,2,4]triazines and some of their derivatives
Authors: Coudert P. , Mavel S. , Couquelet J. , Tronche P. , Rubat C. , Bastide J. 
Published: March 2009

AbstractThe preparation of new dihydropyrazolo[1,5‐d][1,2,4]triazinones involved the formation of carboxylic acid hydrazides via the appropriate ethyl aroylacrylates, followed by condensation with an orthoester. The synthesis of some derivatives substituted on the nitrogen atom in the 5‐position of the triazine ring was reported and their anticonvulsant activity was evaluated.
Syntheses and spectral properties of β‐iodoureas and 2‐amino‐4,4‐diphenyl‐2‐oxazolines
Authors: Fernández José M. García , Mellet Carmen Ortiz , Adrián M. Angeles Pradera , Mota José Fuentes 
Published: March 2009

AbstractThe syntheses of N‐(trans‐2‐iodocyclohexyl)‐ 1–4, N‐(2‐iodo‐3,3‐dimethylbutyl) 5, and N‐(2‐iodo‐1,1‐diphenylethyl)ureas 6, 7 and the cyclization of 6 and 7 into 2‐amino‐2‐oxazoline derivatives 8, 9 are reported. The structures of prepared compounds are based on analytical and spectroscopic data.
Nitrogen Bridgehead Compounds. Part 81. Synthesis of 9‐(benzylidenehydrazono)‐6‐methyl‐4‐oxo‐6,7,8,9‐tetrahydro‐ and 9‐(benzylidenehydrazine)‐6‐methyl‐4‐oxo‐6,7‐dihydro‐4H‐pyrido[1,2‐a]‐pyrimidine‐3‐carboxylates
Authors: Hermecz István , Breining Tibor , Sessi John , Podányi Benjamin 
Published: March 2009

AbstractReaction of ethyl 9‐hydrazono‐6‐methyl‐4‐oxo‐6,7,8,9‐tetrahydro‐4H‐pyrido[1,2‐a]pyrimidine‐3‐carboxylate and benzaldehyde and its derivatives give a tautomeric mixture of 9‐arylidenehydrazono‐6,7,8,9‐tetrahydro‐ and 9‐arylidenehydrazine‐6,7‐dihydropyrido[1,2‐a]pyrimidine derivatives. In the same case the enhydrazine and hydrazone tautomers were separated. The structure of the products were characterised by uv, ir, 1H and 13C nmr. The equilibrium of the tautomers was affected by the substituent of the phenyl ring. A fair linear correlation exists between the logarithms of the equilibrium constants and Hammett σm and σ− constants of the substituents present on the phenyl ring.
Electrochemical oxidation of substituted pyrroles. III. Anodic oxidation of 2,5‐diphenyl‐3‐acetylpyrrole
Authors: Petruso S. , Caronna S. , Gambino S. , Filardo G. , Silvestri G. 
Published: March 2009

AbstractThe electrochemical oxidation of 2,5‐diphenyl‐3‐acetylpyrrole (I) is described. The cyclic derivative 1,6a‐dihydro‐2,5,6a‐triphenyl‐3,4‐diacetylbenzo[g]pyrrolo[3,2‐e]indole (II) was obtained in very good yield. However, when water was present in the reaction medium, a different derivative, 4‐acetyl‐2‐hydroxy‐2,5‐diphenyl‐3‐(4′‐acetyl‐2′,5′‐diphenyl‐3′‐yl)‐2H‐pyrrole (III), was obtained as the main product. 2,2′,5,5′‐Tetraphenyl‐4,4′‐diacetyl‐3,3′‐dipyrryl (IV), a potentially useful intermediate for the synthesis of condensed pyrroles, was synthesized by zinc reduction of III.
Heterocyclization of Acetamidrazones. I. Synthesis of 1,2,4‐triazolo[4,3‐a]pyridines via ring closure of 6‐(2‐acylhydrazino)pyridine intermediates
Authors: Cocco Maria Teresa , Congiu Cenzo , Onnis Valentina , Maccioni Antonio 
Published: March 2009

AbstractThe reaction of N1‐acyl‐2‐ethoxycarbonylacetamidrazones with ethyl ethoxymethylenecyanoacetate (EMCA) has been examined. The acetamidrazone 1a reacts with EMCA in boiling dimethyl sulphoxide to give the 1,2,4‐triazolo[4,3‐a]pyridin‐3(2H)‐one 2 in excellent yield. Similarly from the amidrazones 1b‐h the 1,2,4‐triazolo[4,3‐a]pyridines 3b‐h were obtained. When the reaction between the amidrazones and EMCA was performed in ethanolic solution, the 6‐(2‐acylhydrazino)‐pyridines 4 were isolated. Ring closure of 4 afforded the 1,2,4‐triazolo[4,3‐a]pyridines.
Design and synthesis of the 3′‐aminocarbonylamino, aminothiocarbonylamino and N‐(Hydroxy)guanidinyl derivatives of thymidine as potential anti‐HIV agents
Authors: Morin Kevin W. , Kumar Rakesh , Knaus Edward E. , Wiebe Leonard I. 
Published: March 2009

AbstractThe 3′‐substituted‐3′‐deoxythymidines 3a (urea), 3b (thiourea) and 3c [N‐(hydroxy)guanidinyl)] were designed based on the known structure‐activity correlations for the active anti‐HIV agent, 3′‐azido‐3′‐deoxythymidine (AZT). Hydrolysis of 3′‐cyanamido‐3′‐deoxythymidine (2) with ammonium hydroxide in the presence of hydrogen peroxide afforded the 3′‐urea analogue 3a, whereas reaction with hydrogen sulfide in methanol gave the 3′‐thiourea derivative 3b. The 3′‐[N‐(hydroxy)guanidinyl] compound 3c was synthesized by reaction of the 3′‐cyanamide 2 with hydroxylamine.
A convenient synthesis of 2‐arylidene‐3,8‐dihydro‐2H‐cyclohepta[b]furan‐3,8‐diones
Authors: Jin Zhong‐Tian , Liu Zhong , Imafuku Kimiaki 
Published: March 2009

Abstract3‐(2‐Bromoacetyl)tropolone (1) reacted with several benzaldehydes 2a‐e to afford 2‐arylidene‐3,8‐dihydro‐2H‐cyclohepta[b]furan‐3,8‐diones 3a‐e in very good yields.
Halogenation and nitration of naphtho[1,2‐c][1,2,5]thiadiazole
Authors: Smith Walter T. , Patterson John M. , Kovelesky Albert C. 
Published: March 2009

AbstractBromination of naphtho[1,2‐c][1,2,5]thiadiazole (I) gives either an addition product, 4,5‐dibromo‐4,5‐dihydronaphtho[1,2‐c][1,2,5]thiadiazole (II), or a substitution product, 5,6‐dibromonaphtho[1,2‐c][1,2,5]thiadiazole (III), depending on the reaction conditions. Dehydrobromination of II gives 5‐bromonaphtho[12‐c][1,2,5]thiadiazole (IV). Chlorination of I gives the corresponding addition product V or 5‐chloronaphtho[1,2‐c][1,2,5]thiadiazole (VI). Compound VI can also be obtained by dehydrochlorination of V. The nitration of I produces a mixture of isomeric substitution products, 9‐nitro VIII and 6‐nitronaphtho[1,2‐c][1,2,5]thiadiazoles (VII).
Trifluoromethyl substituted 4‐pyrones via self‐condensation of trifluoroacetoacetates
Authors: Babu Srinivasan , Pozzo Mark J. 
Published: March 2009

AbstractWhen 3‐(acetoxy)‐4,4,4‐trifluoro‐2‐butenoates 7 and 8 are heated at 100°, in the presence of catalytic amounts of zinc chloride, they undergo self‐condensation to yield 2,6‐bis(trifluoromethyl)‐4‐pyrones 1 and 2 respectively. Compounds 1 and 2 were further converted to the corresponding pyridine derivatives 3 and 4 via ammoniolysis.
Preparation of 3‐(2H‐pyran‐2‐on‐6‐yl)indolizines and the diels‐alder reactions with some olefinic and acetylenic dienophiles
Authors: Shimo Tetsuro , Ohe Masayuki , Somekawa Kenichi , Tsuge Otohiko 
Published: March 2009

Abstract3‐(2H‐Pyran‐2‐on‐6‐yl)indolizines 6a‐d were prepared by 1,3‐dipolar cycloaddition reactions of N‐(2H‐pyran‐2‐on‐6‐yl)methylpyridinium bromides 5a,b with dimethyl acetylenedicarboxylate (DMAD). All of the cycloaddition reactions of 6b with N‐phenylmaleimide, p‐benzoquinone, and DMAD took place at the 2‐pyrone ring to give 3‐substituted indolizines.
Synthesis of (1R,4S,5R)‐endo‐N,N‐dimethyl‐2‐azabicyclo[2.2.1]methanamine
Authors: Jordis Ulrich , Sauter Fritz , Siddiqi Suhaib M. 
Published: March 2009

AbstractStarting from trans‐4‐hydroxy‐L‐proline, (1R,4S,5R)‐endo‐N,N‐dimethyl‐2‐azabicyclo[2.2.1]methanamine 1 has been synthesized. The target compound is precursor of antibacterial quinolone carboxylic acids.
Preparation of 2‐formyl‐4‐nitropyrroles
Authors: Ono Noboru , Muratani Emiko , Ogawa Takuji 
Published: March 2009

AbstractThe Vilsmeier reaction of 3‐nitropyrroles which are prepared by the reaction of nitroalkenes with the sodium salt of tosylmethylisocyanide gives 2‐formyl‐4‐nitropyrroles in good yields.
Photochemistry of alkenyl‐ and acetal‐substituted pyridines
Authors: Fleming Steven A. , Bachelder Vance D. 
Published: March 2009

AbstractEthyl 3‐(2‐pyridyl)propionate formation results from irradiation of 3‐(2‐pyridyl)propanal diethylacetal in acetonitrile. This photoreaction is unique to the heteroaromatic pyridine and only occurs in acetonitrile. A minor product, 1‐aza‐2‐methyl‐3‐(2‐ethanal diethylacetal)‐4‐ethoxycycloocta‐1,3,5,7‐tetraene, is also obtained. The irradiation of 2‐methyl‐6‐(2‐pyridyl)‐2‐pentene in the presence of various sensitizers results in addition to the alkene side‐chain to produce oxetanes.
On triazoles. XXVIII. Synthesis of isomeric 1,2,4‐triazolylcarbothiohydrazides
Authors: Barkóczy József , Reiter József 
Published: March 2009

AbstractDifferent 3a, 3b, 9, 10 and 12 type 5‐amino‐1,2,4‐triazolylcarbothiohydrazide isomers representing all possible isomeric types derived from 5‐amino‐1,2,4‐triazoles were synthesised from the corresponding 5‐amino‐1,2,4‐triazolyldithiocarbonates and hydrazines. HPLC measurements proved that in case of mono‐substituted hydrazines the steric press in the intermediate 6 caused besides formation of the expected derivative 3a the formation of compounds 4 and 5, too, while the intermediate 7 yielded only 3b. Thermal rearrangement of derivatives 3a in acetic acid led to isomers 9 and 10, respectively.
Studies on pyrazine. 23. Homolytic acylation of 2‐amino‐3‐cyanopyrazine and the related compounds with α‐keto acids: A synthesis of 5‐acyl‐3‐aminopyrazinecarboxylic acid derivatives
Authors: Sato Nobuhiro , Kadota Hisashi 
Published: March 2009

AbstractHomolytic acylation of 2‐amino‐3‐cyanopyrazine (1) with α‐keto acids led to the formation of 6‐acylated compounds in 74‐85% yields. Methyl 3‐aminopyrazinecarboxylate (2) and 3‐aminopyrazinecarboxamide (3) were also acylated under the same conditions although in lower yields. The observed reactivity of acylation is explained by comparison with the homolytic reactions of related pyrazines.
A convenient synthesis for some new pyrido[3′,2′:4,5]thieno‐[3,2‐d]pyrimidine derivatives with potential biological activity
Authors: Peinador Carlos , Ojea Vicente , Quintela José Ma. 
Published: March 2009

AbstractReady, convenient synthesis for 8‐cyano‐7‐ethoxy‐4‐oxo‐9‐phenyl‐2‐substituted‐1,2,3,‐4‐tetrahydropyrido‐[3′,2′:,4,5]thieno[3,2‐d]pyrimidines 5, 8‐cyano‐7‐ethoxy‐4‐oxo‐9‐phenyl‐2‐substituted‐3,4‐dihydropyrido[3′,2‐: 4,5]thieno[3,2‐d]pyrimidines 6, 4‐chloro‐8‐cyano‐7‐ethoxy‐9‐phenyl‐2‐substitutedpyrido[3′,2′:4,5]thieno[3,2‐4 ‐pyrimidines 7 and 8‐cyano‐7‐ethoxy‐2‐(2′‐nitrophenyl)‐9‐phenyl‐4‐substitutedpyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidines 8‐18 from 2‐chloro‐3,5‐dicyano‐6‐ethoxy‐4‐phenylpyridine 1 via 3,5‐dicyano‐6‐ethoxy‐2‐mercapto‐4‐phenylpyridine 2 and aminocarboxamide 4 are reported. In addition, the reaction of hydrazino derivative 12 with reagents such as formic acid and triethyl orthoformate yielded the fused tetraheterocyclic 8‐cyano‐9‐ ethoxy‐5‐(2′‐nitrophenyl)‐ 7‐phenylpyrido[3′,2′:4,5]thieno[2,3‐e]‐1, 2,4‐triazolo[4,3‐c]pyrimidine system 19.
Synthesis of 4,5‐dihydroisoxazole and isoxazolin‐5‐ones
Authors: Barluenga Joseé , Gotor Vicente , Iglesias María José 
Published: March 2009

AbstractThe synthesis of 5‐hydrazono‐4,5‐dihydroisoxazoles 3, from N'‐(3‐imino‐3‐aryl‐1‐methyl‐1‐alquenyl) hydrazones 1 and hydroxylamine hydrochloride, is described. These 4,5‐dihydroisoxazoles can be transformed into oximes 5 and isoxazolones 6 by treatment with reducing agents and ethyl chloroformate, respectively.
1,2,3‐Thiadiazole derivatives with a nearly linear N‐S…O grouping. X‐ray crystal structure analysis of four methylated products of 4‐phenyl‐1,2,3‐thiadiazole‐5‐carbaldoxime
Authors: L'Abbé Gerrit , Bastin Lieve , Dehaen Wim , Van Meervelt Luc , Feneau‐Dupont J. , Declercq J. P. 
Published: March 2009

AbstractThe title oxime 6 was methylated under different conditions and yielded four monomethylated products 7‐10 and two bismethylated products 11 and 12 which were easily distinguished by their 13C nmr spectra. In view of the potential thiapentalene character of 8, 9, 10 and 11, their X‐ray crystal structures were determined. The structural properties of the nitroso compound 9 are in accordance with a thiapentalene structure, whereas those of the other compounds deviate in the order 10 < 11 < < 8.
Influence of the coordination number of nitrogen on the structure of 6aλ4‐thia‐1,3,4,6‐tetraazapentalenic systems. Crystal structure analyses of 3‐(2‐pyridylimino)‐3H‐[1,2,4]thiadiazolo[4,3‐a]pyridine and its 1‐methylated salt
Authors: L'Abbé Gerrit , Van Meervelt Luc , Emmers Sabine , Dehaen Wim , Toppet Suzanne 
Published: March 2009

AbstractStructural data were obtained by X‐ray crystallography for the title compounds which show that they are essentially planar and exhibit an approximately linear N2‐S1‐N8 arrangement. In compound 3 the separation between the sulfur atom and the pyridine nitrogen atom (2.61 Å) is larger than the Huggins constant energy distance (2.58 Å), suggesting that there is little or no bonding between them. The methylated salt 4, on the contrary, has a closer S…N(pyridine) distance (2.19 Å) with an estimated bond dissociation energy of 6 kcal/mole.
Synthesis and spectral analysis of (±)‐cis‐N‐[1‐(2‐hydroxy‐2‐phenyl‐ethyl)‐3‐methyl‐4‐piperidyl]‐N‐phenylpropanamide and (±)‐cis‐N‐[1‐(2‐hydroxy‐1‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐N‐phenylpropanamide
Authors: Brine G. A. , Sawyer D. K. , Huang P.‐T. , Stark P. A. , Gaetano K. D. , Carroll F. I. 
Published: March 2009

AbstractTreatment of (±)‐cis‐N‐(3‐methyl‐4‐piperidyl)‐N‐phenylpropanamide(2)with styrene oxide(1)yielded a mixture of (±)‐cis‐N‐[1‐(2‐hydroxy‐2‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐N‐phenylpropanamide(3)and (±)‐cis‐N‐[1‐(2‐hydroxy‐1‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐N‐phenylpropanamide(4). The structure of compound3was confirmed by an unambiguous synthesisvia(±)‐cis‐N‐[1‐(2‐oxo‐2‐phenylethyl)‐3‐methyl‐4‐piperidyl]‐N‐phenylpropanamide(6). The proton and carbon‐13 resonances of compounds3and4were assigned with the aid of two‐dimensional heteronuclear correlation experiments.