bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis and properties of conformationally locked 1,3‐bisalkyl‐7‐deazaxanthine 2′‐deoxy‐d‐ribofuranosides
Authors: Seela F. , Kretschmer U. 
Published: March 2009

Abstract1,3‐Dimethyl‐7‐deazaxanthine 2′‐deoxyribofuranosides 1a and 6a and their N‐3 isopropyl congeners 1b and 6b have been prepared employing the nucleobase anions 7a or 7b and 2‐deoxy‐3,5‐di‐O‐(p‐toluoyl)‐α‐D‐erythropentofuranosyl chloride (8) upon glycosylation. The reaction was not stereoselective as found in case of other pyrrolo[2,3‐d]pyrimidine nucleosides induced by the bulky N‐3 substituent. Configuration of anomers was established by 1H‐nmr nOe difference spectroscopy. Those data also indicated that the conformation around the N‐glycosylic bond was locked by the bulky N‐3 substituent. Contrary to the purine nucleoside such as wyosine (2a) the hydrolytic stability of the N‐glycosylic bond of the pyrrolo[2,3‐d]pyrimidine nucleosides was increased by N‐3 alkylation. Moreover, it was shown by 15N‐nmr spectroscopy that different to purine nucleosides the aglycon was not protonated in acidic medium. As a result the N‐glycosylic bond hydrolysis did not follow an A‐1 but an A‐2 mechanism.
A convenient synthesis of 3‐aryl‐1,2,4‐triazolo[4,3‐c]quinazolines
Authors: El‐Kerdawy Mohamed M. , Ismaiel Abd El‐Kader M. , Gineinah Magdy M. , Glennon Richard A. 
Published: March 2009

AbstractThe synthesis and characterization of several 3‐aryl‐1,2,4‐triazolo[4,3‐c]quinazolines is described. The first step comprises the condensation of aromatic aldehydes with 2‐(H or Cl)‐4‐hydrazinoquinazolines 2 to afford the corresponding hydrazones 3. The second step involves the cyclization to the title compounds 4 in bromine/acetic acid. Reaction of 4 (X = Cl) with cyclic amines gave the corresponding 5‐cyclicamino 5 or 5‐alkoxy derivatives 6.
The synthesis of hexahydro‐6H‐dibenzo[b,d]pyrans: Derivatives of 9‐Nor‐9β‐hydroxyhexahydrocannabinol
Authors: Melvin Lawrence S. , Bordner Jon , Hada William A. , Johnson M. Ross 
Published: March 2009

AbstractTo assess the importance of the phenol functionality in cannabinoids for analgetic activity a new series of 9‐nor‐9β‐hydroxyhexahydrocannabinoids was prepared. The synthesis of 1‐substituted (H, CH2OH, OH, NH2) 6aβ,7,8,9,10,10aα‐hexahydro‐9β‐hydroxy‐6,6‐dimethyl‐3‐[1‐methyl‐4‐phenylbutoxy]‐6H‐dibenzo[b,d]pyrans from 3,5‐dihydroxystilbene, 3,3′,5,5′‐tetrahydroxystilbene or 1,3,5‐trihydroxybenzene is described. Relative stereochemistry and structure confirmations were obtained by nmr and X‐ray crystal analysis.
Synthesis of 6‐substituted‐4,5‐dihydro‐3(2H)‐pyridazinones
Authors: Baraldi P. G. , Chiarini A. , Leoni A. , Manfredini S. , Simoni D. , Zanirato V. 
Published: March 2009

AbstractA convenient synthetic method for the pharmaceutically important 6‐substituted‐4,5‐dihydro‐3(2H)‐pyridazinones is described. The synthetic strategy is based on Δ‐soxazolines chemistry which were in turn unmasked by NO bond cleavage and cyclized to the target compounds.
Murexide reaction of caffeine with hydrogen peroxide and hydrochloric acid. II
Authors: Koyama Matajiro , Kozuka Hiroshi 
Published: March 2009

AbstractIn continuation of the study on the murexide reaction of caffeine with 3% hydrogen peroxide/hydrochloric acid and then with ammonia giving a purple coloration, we investigated the oxidation reaction of caffeine with 6% hydrogen peroxide/hydrochloric acid to isolate ten reaction products, 3‐hydroxy‐4,6‐dimethyloxazolo[4,5‐d]pyrimidine‐2,5,7(3H,4H,6H)‐trione 1, 1,3‐dimethylalloxan 2, murexoin 3, 1,3,7‐trimethyl‐2,6,8‐trioxo‐9‐hydroxy‐1H,3H,7H‐xanthine 5, 1,3,7‐trimethyl‐2,6,8‐trioxo‐1H,3H,7H‐xanthine 6, 1,3,7‐trimethyl‐2,6‐dioxo‐8‐chloro‐1H,3H,7H‐xanthine 7, 5‐(1,3‐dimethyl‐1,2,3,4,5,6‐hexahydro‐2,4,6‐trioxopyrimidin‐5‐yl)‐aminomethylene‐1,3‐dimethyl‐1,2,3,4,5,6‐hexahydro‐2,4,6‐trioxopyrimidine ammonium salt 9, 1,3‐dimethylpalabanic acid 10, 1‐methyl‐2,4,5‐trioxoimidazole 11, 3‐hydroxy‐5,7‐dimethyloxazolo[5,4‐d]pyrimidine‐2,4,6(3H,5H,7H)‐trione 12 and 4,6,8‐trimethyl‐1,2,4‐dioxazino[6,5‐d]pyrimidine‐3,5,7(4H,6H,8H)‐trione 13.The oxidation reaction using 6% hydrogen peroxide/hydrochloric acid was found to produce a similar purple coloration to that of the murexide reaction despite no subsequent addition of ammonia, indicating the liberation of ammonia by the oxidation of caffeine.Among the above compounds, the purple colored substance murexoin 3 and the yellow colored compound 9 were both ammonium salts, and compound 5 was the red colored substance. In the present investigation, these three compounds were found to contribute to the coloration.
Intramolecular cyclization of 4‐acetyl‐2,2‐diethoxycarbonyl‐2,3‐dihydro‐1‐(2‐nitrobenzoyl)pyrrole by catalytic reduction
Authors: De Caprariis P. , De Martino G. , Abignente E. , Sacchi A. 
Published: March 2009

AbstractCatalytic hydrogenation of 4‐acetyl‐2,2‐dicthoxycarbonyl‐2,3‐dihydro‐1‐(2‐nitrobenzoyl)pyrrole 2 afforded 3‐acetyl‐1,1‐diethoxycarbonyl‐1,2,3,3a,4,9‐hexahydro‐9‐oxopyrrolo[2,1‐b]quinazoline 3 and the 4‐hydroxy derivative 4, together with two tetrahydro analogs 5 and 6 of 3. Compounds 5 and 6 were also obtained by dehydration of 4.
Mesoionic 1,2,4‐triazolo[4,3‐c]quinazolines
Authors: Gineinah Magdy M. , Ismaiel Abd El‐Kader M. , El‐Kerdawy Mohamed M. , Glennon Richard A. 
Published: March 2009

AbstractBecause of the close structural similarity between triazoloquinazolines and certain 5‐membered ring mesoionic heterocycles, all of which possess antiinflammatory activity, we prepared several examples of the novel mesoionic 1,2,4‐triazolo[4,3‐c]quinazoline ring system for their therapeutic potential. These compounds can be prepared by the cyclization of the appropriately substituted 4‐hydrazinoquinazolines with phosgene. When the mesoionic product was unsubstituted at the 5‐position (i.e., quinazoline 2‐position), it could only be isolated as its hydrochloride salt and not as its unstable free base. None of the mesoionic products were sufficiently stable in solution to allow for evaluation of their antiinflammatory activity.
Synthesis of pyrazolo[3,4‐d]pyrimidine derivatives using ketene dithioacetals
Authors: Tominaga Yoshinori , Honkawa Yasumasa , Hara Mayumi , Hosomi Akira 
Published: March 2009

AbstractThe cyclization of 5‐amino‐3‐methylthiopyrazole‐4‐carbonitriles or 4‐carboxamides 3a‐j, which were prepared by the reaction of ketene dithioacetals 1a,b [1a: bis(methylthiomethylenemalononitrile; 1b: bis(methylthio)methylenecyanoacetamide] with hydrazines (hydrazine hydrate, phenylhydrazine, p‐chlorophenylhydrazine, p‐nitrophenylhydrazine), with formamide or carbon disulfide proceeded to give the corresponding 4‐amino‐ or 4‐hydroxy‐3‐methylthiopyrazolo[3,4‐d]pyrimidines 6a‐h in good yields. 3‐Aminopyrazolo[3,4‐d]pyrimidine derivatives 6i‐1 were also obtained by the application of the cyclization reaction of 3,5‐diaminopyrazoles with formamide.
3‐(2‐Pyrrolidinyl)‐2,4‐furandione analogs
Authors: Coppola Gary M. , Damon Robert E. 
Published: March 2009

AbstractThe reaction of 4,4‐dimethyl‐3‐oxobutanoic (or pentanoic) acid esters with the lactim ether of 2‐pyrrolidone in the presence of 2‐hydroxypyridine produces condensation products 4 in 57–72% yield. Acidic hydrolysis of 4 affords the furandione system 5 in 75–81% yield.
A Facile synthesis of 3‐alkylthio‐(or arylthio‐)pyridines and 3,5‐bis(alkylthio)pyridines
Authors: Chen Ted K. , Flowers William T. 
Published: March 2009

Abstract3‐Alkylthio‐ (or 3‐arylthio‐)pyridines and 3,5‐bis(alkylthio)pyridine can be conveniently prepared by the reaction of 3‐thiocyanato‐ or 3,5‐bis(thiocyanato)pyridines with tri‐n‐butylphosphine in the presence of alcohol.
Furan derivatives. Part 12 . Synthesis of 2,5‐dioxacyclohepta[jkl]‐as‐indacenes
Authors: Horaguchi Takaaki , Miyazawa Kazuhiro , Hasegawa Eietsu , Shimizu Takahachi , Suzuki Tsuneo , Tanemura Kiyoshi 
Published: March 2009

AbstractA variety of 2,5‐dioxacyclohepta[jkl]‐as‐indacenes 5, 7–14 were synthesized as a new heterocycle by the treatment of diethyl (5,9‐dioxobenzocyclohepten‐1,4‐diyloxy)diacetates 4a‐e with potassium hydroxide or sodium hydride in dioxane. The mechanism of furan‐ring formation from 4a‐e was discussed.
Polycondensed nitrogen heterocycles. Part 23. Pyrrolo[3,2‐c]cinnolines by a japp‐klingemann type reaction
Authors: Cirrincione Girolamo , Almerico Anna Maria , Aiello Enrico , Dattolo Gaetano 
Published: March 2009

AbstractPyrrolo[3,2‐c]cinnoline derivatives were obtained by an unusual Japp‐Klingemann reaction involving an intramolecular azadehalogenation on the pyrrole nucleus. Such an azadehalogenation represents the first example of Japp‐Klingemann reaction in which the extrusion of positive chlorine ion is verified.
Structure and synthesis of the metribuzin blue dye. Synthesis and reactions of 2,5‐dihydrazino‐1,3,4‐thiadiazole and its derivatives
Authors: Jackman Dennis Earl 
Published: March 2009

AbstractA blue pigment which sometimes accompanies the manufacture of the triazine herbicide metribuzin (5) was identified as the novel thiadiazole formazan 10 which arises from the reaction of two impurities 3 and 7. The latter compound is a keto acid derivative of 2,4‐dihydrazinothiadiazole which in turn is an impurity in carbonothioic dihydrazide. Compound 7 has the interesting property of undergoing a facile oxidative decarboxylation in the presence of alcohols to form hydrazonate esters and in the presence of aliphatic amines to form red amidrazone dyes 9. The N‐substituted dyes can be oxidized to ditriazolothiadiazoles 12.
On the synthesis of thieno[3,2‐c]quinoline N‐oxide and thieno‐[3,2‐C]isoquinoline N‐oxide. The nmr spectra of the six isomeric thieno‐fused quinoline and isoquinoline N‐oxides
Authors: Gronowitz Salo , Timari Géza 
Published: March 2009

AbstractThe synthesis of the two remaining isomeric monothieno‐analogues of phenanthridine N‐oxide, thieno‐[3,2‐c]quinoline N‐oxide and thieno[3,2‐c]isoquinoline N‐oxide, is described. The 1H and 13C nmr spectra of all six isomeric thieno‐fused quinoline and isoquinoline N‐oxides are discussed.
Synthesis of 5‐benzyl and 5‐benzyloxybenzyl‐3′‐azido‐2′,3′‐dideoxyuridine and their analogues as potential anti‐AIDS agents
Authors: Pan Bai‐Chuan , Weng Zum‐Yao , Chen Zhi‐Hao , Rowe Elizabeth C. , Chu Shih‐Hsi 
Published: March 2009

Abstract5‐Benzyl and 5‐benzyloxybenzyl‐substituted 3′‐azido‐2′,3′‐dideoxyuridine, (8a and 8b), 3′‐halogeno‐2′,3′‐dideoxyuridine, 9a, 9b, 10a, 10b, 11a and 11b, and 2′,3′‐dideoxyuridine, 12a and 12b, of Scheme I were synthesized as potential anti AIDS agents. Synthesis of epimers of 8a and 8b, 5‐benzyl‐ and 5‐benzyloxybenzyl‐1‐(3′‐azido‐2′,3′‐dideoxy‐β‐D‐threo‐pentafuranosyl)uracil, 15a and 15b, and 5‐benzyl‐ and 5‐benzyloxy‐5′‐azido‐2′,5′‐dideoxyuridine, 16a and 16b, shown in Scheme II, were also reported.
A novel synthetic route to 2‐halo‐3,4‐dicyanopyridines
Authors: Lee Ju‐Yeon , Hall H. K. 
Published: March 2009

Abstract2‐Bromo‐3,4‐dicyanopyridine 2 was obtained in moderate yield by reacting 1,1,2,2‐tetracyano‐3‐trimethylsiloxycyclobutane 1 with phosphorus tribromide. Similarly, reaction of 1 with chlorinating reagents such as thionyl chloride and oxalyl chloride led to the corresponding 2‐chloro‐3,4‐dicyanopyridine 3 in 40% yield. A reaction mechanism is suggested.
Orientational effect of the phenylsulfonyl group in the thermal spiroketalization of dihydroxyketone equivalents
Authors: Alzérreca Arnaldo , Avilés Mayra , Collazo Luis , Prieto Antonio 
Published: March 2009

AbstractThe thermal cyclization of a dihydroxyketone equivalent 4b leads to the predominant formation of crystalline 4‐(benzenesulfonyl)‐1,6‐dioxaspiro[4.5]decane (8). Under similar reaction conditions the tetrahydrofuranylidene derivative 6 is obtained from ketone 4c. It does appear that the phenylsulfonyl group is a factor which influences the course of the reaction leading to the preferential formation of one of the possible stereoisomers.
Synthesis of 9‐(hexane‐1,6‐diol‐3‐yl)purines, a novel series of acyclic nucleoside analogs and antiviral evaluation
Authors: Legraverend Michel , Boumchita Hassane , Bisagni Emile 
Published: March 2009

AbstractNew acyclic purine nucleoside analogs lacking the C(3′)C(4′) bond, have been prepared from 4‐aminocyclohexene and evaluated for antiviral activity. A new synthesis of 4‐aminocyclohexene from cyclohex‐3‐ene‐1‐carbonyl chloride is also reported via a Curtius reaction. None of the two compounds exhibited any antiviral activity in vitro against HSV‐1, HCMV and HIV‐1.
Acetylenic chemistry. Part 17 Acetylenic amides as precursors for the synthesis of 3‐propynylquinazolinones
Authors: Reisch J. , Usifoh C. O. , Oluwadiya J. O. 
Published: March 2009

AbstractCyclocondensation of acetylenic amides with triethylorthoformate and triethylorthoacetate in boiling glacial acetic acid under nitrogen gave 3‐propynylquinazolinones. 2‐Ethoxy‐2‐methyl‐3[1,1‐dimethylpropynyl]quinazolin‐4(1H,3H)‐one (3b) and 2‐ethoxy‐2‐methyl‐3‐[1‐cyclohexylpropynyl]quinazolin‐4(1H,3H)‐one (3c) in refluxing ethanolic sodium hydroxide afforded the corresponding oxazoloquinazolinones.
Synthèse de L'hydroxy‐9 pyrimido[1,6‐a]pyrimidine one‐4 et dérivés
Authors: Dennin F. , Blondeau D. , Sliwa H. 
Published: March 2009

AbstractLa condensation d'alcoxy‐5 amino‐4 pyrimidines avec l'éthoxyméthylènemalonate de diéthyle et avec le méthoxyméthylènemalonate d'isopropylidène conduit après cyclisation thermique des intermédiaires énaminoesters résultants aux alcoxy‐9 pyrimido[1,6‐a]pyrimidines one‐4 substituées par un groupe éthoxycarbonyle en 3 dans le premier cas. L'hydrogénolyse des éthers benzyliques correspondants permet d'obtenir de nouveaux phénols hétérocycliques: l'hydroxy‐9 pyrimido[1,2‐a]pyrimidine one‐4 et son dérivé éthoxycarbonylé en 3.
Synthesis of α‐(aminomethylene)‐9‐(methoxymethyl)‐9H‐purine‐6‐acetic acid derivatives
Authors: Hamamichi Norimitsu , Miyasaka Tadashi 
Published: March 2009

Abstractα‐(Aminomethylene)‐9‐(methoxymethyl)‐9H‐purine‐6‐acetamide and the ethyl acetate, 3 and 8, have been synthesized by catalytic hydrogenation of 6‐cyanomethylene‐9‐methoxymethylpurine derivatives 2 and 7 which were obtained by the substitution of 6‐chloro‐9‐(methoxymethyl)purine (1) with α‐cyanoacetamide and ethyl cyanoacetate, respectively. Substitution of 3 and 8 with amines gave the corresponding N‐substituted α‐(aminomethylene)‐9‐(methoxymethyl)‐9H‐purine‐6‐acetamide and the ethyl acetate 4 and 10. Reaction of 3 with piperidine gave 9‐(methoxymethyl)‐9H‐purine‐6‐acetamide (5).
Molecular rearrangements of 4‐iminomethyl‐1,2,3‐triazoles. Replacement of 1‐aryl substituents in 1H‐1,2,3‐triazole‐4‐carbaldehydes
Authors: L'abbé Gerrit , Bruynseels Maria , Delbeke Pieter , Toppet Suzanne 
Published: March 2009

AbstractThe two structural isomers, 4 and 5, of 1‐substituted‐4‐iminomethyl‐1,2,3‐triazoles are interconvertible when heated in dimethyl sulfoxide at 80°. The equilibrium position depends on the electronic properties of the R‐substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p‐chlorophenyl and p‐nitrophenyl. An interesting application is the synthesis of 1‐alkyl‐1,2,3‐triazole‐4‐carbaldehydes from 1‐phenyl‐1,2,3‐triazole‐4‐carbaldehyde by Scheme I. The hydrazones 4ij and the oxime 4k do not rearrange due to an unfavorable Z‐configuration around the C  N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11. The structures of the products have been fully characterized by 13C nmr spectroscopy and the mechanistic details of the rearrangement are discussed.
Preparation of β‐hydroxysulfides from 1,2,3‐thiadiazoles. Comparison of the effect of phenylmagnesium bromide on α‐Thio‐ and α‐selenoketones
Authors: Ganjian Iraj 
Published: March 2009

AbstractBase decomposition of 4‐substituted‐phenyl‐1,2,3‐thiadiazoles at 78° resulted in 2‐(4‐substituted‐phenyl)‐ethynylthiolate anions which were immediately reacted with α‐bromoketones to give a series of α‐(2‐[4‐substituted‐phenyf]ethynyl) thioketones. Unlike the selenophilic reaction of the Grignard reagents with α‐selenoketones, the carbonyl group was the site of nucleophilic attack and the reaction of the α‐thioketones with phenylmagnesium bromide gave the corresponding β‐hydroxysulfides. The difference in mode of action toward the Grignard reagents was attributed to the difference in the bond strengths between carbon and the heteroatoms.
Synthesis of diastereomeric ketoconazole analogs
Authors: Chapman David R. , Bauer Ludwig , Waller Donald P. , Zaneveld Lourens J. D. 
Published: March 2009

AbstractSyntheses of trans‐isomers of ketoconazole, and the corresponding des‐acetyl, 1‐methyl‐, 1‐formyl and 1‐methanesulfonyl analogs were investigated. These isomers, along with the corresponding cis‐diastereomers were characterized by their carbon‐13 nmr spectra.
Synthesis and preliminary biological evaluation of 5‐fluoro‐5,8‐dideazaisoaminopterin
Authors: Tomažič Alenka , Hynes John B. , Gale Glen R. , Freisheim James H. 
Published: March 2009

AbstractThe new folate antagonist, 5‐fluoro‐5,8‐dideazaisoaminopterin was synthesized in four steps beginning with 2,4‐diamino‐5‐fluoroquinazoline. It was found to be a potent inhibitor of human dihydrofolate reductase. Against L1210 leukemia in mice, 5‐fluoro‐5,8‐dideazaisoaminopterin was equiactive with methotrexate at approximately one half of the total dose employed.
A facile synthesis of 5,14‐methano‐16‐oxo‐1,5,6‐benzoxadiazonino[3,4‐b]quinoxalines by a 1,3‐dipolar cycloaddition reaction and an intramolecular alcoholysis
Authors: Kurasawa Yoshihisa , Kim Ho Sik , Katoh Ritsuko , Kawano Tae , Takada Atsushi , Okamoto Yoshihisa 
Published: March 2009

AbstractThe reaction of the hydrazones 5a‐c with 2‐chloroacrylonitrile gave the 1,2‐diazepino[3,4‐b]quinoxaline hydrochlorides 6a‐c, which were converted into the 5,14‐methano‐16‐oxo‐1,5,6‐benzoxadiazonino[3,4‐b]‐quinoxalines 7a‐c, respectively.
Ring‐opening reaction in acidic conditions of tetraazapentalene derivatives containing a hypervalent sulfur
Authors: Tomura Masaaki , Matsumura Noboru , Mori Osamu , Chikusa Hisashi , Kamitani Shigeki , Inoue Hiroo 
Published: March 2009

AbstractThe 10‐S‐3 type tetraazapentalene derivatives in acidic conditions were converted to the ring‐opeining products, 1,3‐disubstituted perhydropyrimidin‐2‐ones, in high yields with the release of a hypervalent sulfur.
Synthesis of 2,3,11,12,20,21,29,30‐octadodecylthio‐2,3‐naphthalocyanines
Authors: Kitahara Kiyoshi , Asano Toyofumi , Hamano Ken‐ichi , Tokita Sumio , Nishi Hisao 
Published: March 2009

AbstractThe title compounds were synthesized. They were soluble in organic solvents and their Q bands showed bathochromic shifts compared with unsubstituted 2,3‐naphthalocyanines.
Reduction of the 1,2,5‐thiadiazole ring of 3,6:12,15‐di‐1,4‐benzo[6.6](3,4)‐1,2,5‐thiadiazolo‐ and 3,5:11,13‐di‐1,3‐benzo‐[6.6](3,4)‐1,2,5‐thiadiazolocyclophanes. Selective preparation of cis‐ and trans‐[23]cyclophane‐1,2‐diacetoamide
Authors: Hatta Taizo , Mataka Shuntaro , Tashiro Masashi , Numano Katsutoshi , Suzuki Hiroshi , Tori‐I Akiyoshi 
Published: March 2009

AbstractThe effect of the [2.2.2]cyclophane ring structure on the reduction of 1,2,5‐thiadiazole ring incorporated in cyclophanes 1a‐c and 2a‐c was investigated. When reduced by sodium metal in ethanol followed by acetylation, para[23]cyclophane 1 gave a mixture of the expected cis‐ and trans‐diamides, 3 and 4, in which 4 was the major product. On the other hand, reduction of 1 with lithium aluminum hydride proceeded in a cis‐selective manner and gave 3 as a major product after a treatment of the reduced products with acetic anhydride. The reduction of metacyclophane 2, which is less strained than 1, proceeded exclusively in cis‐fashion and a subsequent treatment of the reduction product with acetic anhydride gave only cis‐diamide 6.
Synthese de pyrrolo[1,2‐a]quinoleines
Authors: Bouyazza Lahboub , Lancelot Jean‐Charles , Rault Sylvain , Robba Max 
Published: March 2009

AbstractLes 4‐acétoxy pyrrolo[1,2‐a]quinoléines 26‐30 sont accessibles par cyclisation des acides 2‐(1‐pyrrole)phénylacétiques 21‐25 par chauffage dans l'anhydride acétique. Les chlorures d'acides 11‐15 constituent les intermédiaires permettant l'accès aux 2‐(1‐pyrrolyl) diazoacétophénones 16‐20 et aux acides phénylacétiques. Les spectres de rmn confirment la structure des dérivés obtenus.
4,5,6,7‐Tetrahydro‐1H‐imidazo[4,5‐c]pyridine‐6‐carboxylic acids (spinacines)
Authors: Klutchko Sylvester , Hodges John C. , John Blankley C. , Colbry Norman L. 
Published: March 2009

AbstractNew derivatives of the naturally occurring amino acid 4,5,6,7‐tetrahydro‐1H‐imidazo[4,5‐c]pyridine‐6‐carboxylic acid (spinacine) are reported. These include amide, ester, 5‐alkyl and acyl, and regiospecificNim‐alkyl and aralkyl derivatives. Synthesisviathe Pictet‐Spengler reaction onNim‐substituted histidines is described. Cyclic hydantoin derivatives of spinacines are included.
Nouvelle méthode d'accès aux benzo[h]furo[3,2‐c]quinoléines, analogues isostériques des benzo[c]phénanthridines
Authors: Duval O. , Mavoungou Gomès L. 
Published: March 2009

AbstractUne synthèse originale des benzo[h]furo[3,2‐c]quinoléines est décrite. L'hydrogénation des dérivés d'addition diénique 5 conduit aux composés 6. Leur pyrolyse suivie d'une saponification permet d'isoler les diacides 9. Les lactames 12 sont alors obtenus par chauffage en présence d'acétate d'ammonium et d'acide acétique anhydres et les lactones 10 par ébullition dans l'anhydride acétique. Des dérivés du noyau benzo[h]‐furo[3,2‐c]quinolone sont alors obtenus par modulation de la fonction acide carboxylique introduite en position 7 ou par fonctionnalisation de la position 6.
Novel 7‐substituted quinolone antibacterial agents. Synthesis of 7‐alkenyl, cycloalkenyl, and 1,2,3,6‐tetrahydro‐4‐pyridinyl‐1,8‐naphthyridines
Authors: Laborde Edgardo , Kiely John S. , Lesheski Lawrence E. , Schroeder Mel C. 
Published: March 2009

AbstractA convergent synthesis of 1,8‐naphthyridine antibacterials bearing a carbon‐carbon bonded, acyclic or cyclic vinyl substituent at the C‐7 position has been achieved. The synthetic methodology is based upon the palladium‐catalyzed cross coupling of a 7‐chloro‐1,8‐naphthyridine with an appropriately substituted organotin reagent.
Reactions of 2,3‐disubstituted 6,7‐dihydro‐5H‐2a‐thia(2a‐SIV)‐2,3,4a,7a‐tetraazacyclopent[cd]indene‐1,4(2H,3H)‐dithiones with isothiocyanates and isocyanates
Authors: Tomura Masaaki , Mori Osamu , Matsumura Noboru , Inoue Hiroo 
Published: March 2009

Abstract12π‐Tetraazapentalenes, 2,3‐disubstituted 6,7‐dihydro‐5H‐2a‐thia(2a‐SIV)‐2,3,4a,7a‐tetraazacyclopent‐[cd]indene‐1,4(2H,3H)‐dithiones, 1 and 7, reacted with excess alkyl or aryl isothiocyanates and isocyanates to afford mono‐ and di‐alkyl or aryl substituted tetraazapentalene derivatives which have the thiocarbonyl and carbonyl groups.
Polycyclic N‐hetero compounds. XXXVI. Syntheses and antidepressive evaluation of 11,13,15,17‐tetraazasteroids and their 17‐oxides
Authors: Hirota Takashi , Sasaki Kenji , Yamamoto Hiroshi , Nakayama Taiji 
Published: March 2009

AbstractSyntheses of 11,13,15,17‐tetraazasteroids, their B‐homologues, and 17‐oxide derivatives are described. Antidepressive evaluation of these compounds and their precursors were screened by inhibitory action of reserpine‐induced hypothermia.
Synthesis of unsymmetrical diheteroarylbenzenes: Benzoazole and quinazoline derivatives
Authors: Garín Javier , Meléndez Enrique , Merchán Francisco L. , Merino Pedro , Orduna Jesús , Tejero Tomás 
Published: March 2009

AbstractFour different types of structures, namely 8, 14, 17 and 18 have been prepared for the first time. No more than five steps are needed to synthesize them using 4‐nitroaniline as starting material. In order to confirm the proposed structures, some independent syntheses have been carried out.