bluuebunny/crossref_metadata_2025_split huggingface dataset:
Susceptibility of morpholine substituents to photo‐oxidative decomposition‐identification of photo‐oxidative degradants of linezolid (PNU‐100766)
Authors: Martin Gary E. , Robins Russell H. , Bowman Phil B. , Duholke Wayne K. , Farley Kathleen A. , Kaluzny Brian D. , Guido Jane E. , Sims Sandra M. , Thamann Thomas J. , Thompson Brian E. , Nishimura Toshihide , Noro Yukimi , Tahara Tsutoma 
Published: March 2009

AbstractParenteral formulations of linezolid (PNU‐100766), a novel (S)‐3‐(4′‐fluorophenyl)‐5‐N‐acetamidomethyloxazolidin‐2‐one antibiotic, were subjected to photo‐stability testing as required by ICH guidelines. Direct, reversed phase chromatographic evaluation of the photo‐irradiated solutions revealed two chromatographically broad degradants. Following preparative chromatographic isolation, the structures of both degradants were determined by mass spectrometric, nmr, and vibrational spectroscopic methods. The degradant structures formed by decomposition involving photo‐oxidation of the morpholine, followed by a carbon‐carbon bond scission to a formyloxyethylformamide‐containing degradant. Facile hydrolytic cleav age of the formate ester in acidic media gave the second chromatographically broad degradant containing a N‐2‐hydroxyethylformamide group. The formamide substituent underwent further hydrolysis in acidic media to the corresponding secondary amine.
Reactions of N‐aryl‐1H‐benzotriazolyl‐1‐methanamines with allyl trimethylsilanes. A facile route to trialkylsilane tetrahydroquinolines
Authors: Katritzky Alan R. , Cui Xilin , Long Qiuhe 
Published: March 2009

AbstractN‐Aryl‐1H‐benzotriazolyl‐1‐methanamines 1, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo Lewis acid assisted reactions with allyl trimethylsilanes to give 4‐(trimethylsilyl)methyl‐1,2,3,4‐tetrahydroquinolines 2 in good to high yields.
Borane complexes of 2‐(1‐Methyl‐1,2,5,6‐tetra‐hydropyridin‐3‐yl)benzoxazoles
Authors: Jung Myung Hee , Park Jewn‐Giew , Ryu Bok‐Sim , Cho Kui‐Woong 
Published: March 2009

Abstract2‐Pyridin‐3‐ylbenzoxazoles were synthesized by the reaction between 3‐pyridinecarboxaldehyde and substituted o‐aminophenols in the presence of iodobenzene diacetate. The resulting benzoxazoles 3 were treated with methyl iodide to give the corresponding pyridinium salts 4 which underwent the hydride reduction with sodium borohydride or sodium cyanoborohydride to produce 2‐(1‐methyl‐1,2,5,6‐tetrahy‐dropyridin‐3‐yl)benzoxazole borane complex derivatives.
Synthesis and spectral properties of 5‐methylthio‐4H‐1‐(p‐substituted‐phenyl)‐3a‐(p‐substituted‐phenyl)‐9‐[(m‐; and p‐substituted)‐phenoxy]‐3a,4‐dihydro[1,2,4]oxadiazolo[4,5‐a][1,5]benzodiazepines
Authors: Cortés Eduardo CortÉS , Cruz Elide HernÁNdez , Mellado Olivia GarcÍA 
Published: March 2009

AbstractThe preparation of eight novel substituted [1,2,4]oxadiazolo[4,5‐a][1,5]benzodiazepines which have potentially useful pharmacological properties; by 1,3‐cycloaddition of benzonitrile oxides, generated in situ from benzohydroxamoyl chloride and triethylamine, to 1,5‐benzodiazepine derivatives is described. The structure of all products was corroborated by ir, 1H‐nmr, 13C‐nmr and ms.
New compounds in the reaction of aromatic amines and 5‐hydroxy‐4‐pyrone‐2‐carboxylate. The influence of a methoxy group
Authors: Kožul M. , Stiplošek Z. , Orhanović Z. , Jakopčić K. , Nagl A. , Hergold‐Brundić A. 
Published: March 2009

AbstractUnlike most of other aromatic amines, 4‐methoxyaniline with methyl comenate (1) in the mixture of acetic acid and methanol (1:1) gave two unexpected products with azomethyne moiety. The structures of new compounds were determined from their characteristic spectroscopic behaviour and were confirmed by X‐ray crystallographic measurements.
Studies on the preparation of 3,4‐disubstituted 2‐methoxypyridines
Authors: Pelisson Marcelo M. M. , Silva Gil Valdo José Da , Clive Derrick L. J. , Coltart Don M. , Hof Fraser A. 
Published: March 2009

AbstractThe synthesis of 2‐methoxy‐4‐methylpyridine‐3‐carbonitrile (3) and its conversion, by way of alkylation of the C(4) methyl group, into the pyrodyl acetic acid ester 6 is described.
Synthesis and spectral data of unknown lilolidine spiro derivatives
Authors: Palma R Alirio , Silva Javier , Stashenko Elena , Martínez Jairo René , Kouznetsov Vladimir 
Published: March 2009

AbstractA new series of halo and methyl substituted spiro annulated tetrahydropyrrolo[3,2,1‐ij]quinolines, analogues of lilolidine alkaloids has been prepared in a two‐step route from easily accessible dihydroquinoline precursors.
2‐Aryl‐7,7‐dimethyl‐5,6,7,8‐tetrahydrothieno[3,2‐c]azepin‐4‐ones from 5,5‐dimethyl‐1,3‐cyclohexanedione
Authors: Martinez Roberto , Durán L Ma. Esther , Cortés L César , Avila Z J. Gustavo 
Published: March 2009

AbstractA novel synthesis of substituted thieno[3,2‐c]azepinones is described. This new approach uses 5,5‐dimethyl‐1,3‐cyclohexanedione (dimedone) as the starting material. Oxime intermediates are obtained in three steps from the aforementioned diketone. Using these intermediates, the title compounds are synthesized in moderate yields.
Synthesis of new pyrazolo[4,3‐c]quinolin‐3‐one derivatives and some oxazolo[4,5‐c]quinoline‐2,4‐diones
Authors: Ismaïli Lhassane , Refouvelet Bernard , Robert Jean François 
Published: March 2009

AbstractThe new pyrazolo[4,3‐c]quinolin‐3‐one derivatives 3a‐c and 6a‐c were prepared by the following three steps: first the preparation of ethyl 4‐hydroxyquinoline‐3‐carboxylate derivatives 1 and 4 by reaction of isatoic anhydrides and ethyl malonate and ethyl acetoacetate respectively, then chloration of 1 and 4 with phosphorus oxychloride to give 2 and 5 and finally the condensation of 2 and 5 with hydrazine and its derivatives. In addition, the successful synthesis of oxazolo[4,5‐c]quinoline‐2,4‐diones 9a‐f are reported.
Synthesis of pyrido[4,3,2‐de]quinazolines via nitro‐substituted tetrahydroquinolines
Authors: Katritzky Alan R. , Strah Sonja , Tymoshenko Dmytro O. , Johnson Graham 
Published: March 2009

AbstractThe simple and efficient synthesis of novel dihydropyrido[4,3,2‐de]quinazolines in four steps from m‐nitroaniline is described.
Polycyclic N‐heterocyclic compounds. 55. A novel reaction of N‐(5,6‐dihydro[1]benzothiepino[5,4‐d]pyrimidin‐4‐yl)amidine or its amide oxime derivatives with hydroxylamine
Authors: Zhang Ying‐Xue , Sasaki Kenji , Hirota Takashi 
Published: March 2009

AbstractThe reactions of N‐(5,6‐dihydro[1]benzothiepino[5,4‐d]pyrimidin‐4‐yl)amidines or its amide oxime derivatives with hydroxylamine hydrochloride under basic condition gave abnormal cyclization products via a ring cleavage of pyrimidine component accompanied with a ring closure of [1,2,4]oxadiazole.
Sulfenylation of heterocyclic 1,3‐dicarbonyl systems: 4‐Hydroxy‐2‐pyrones, 6‐hydroxy‐4‐pyrimidones, 4‐hydroxy‐2‐pyridones, 4‐hydroxy‐6‐pyridazinones, and 5‐hydroxy‐3‐pyrazolones
Authors: Schnell Barbara , Kappe Thomas 
Published: March 2009

AbstractAnions of enolized heteroaromatic 1,3‐dicarbonyl systems, such as the title compounds 1, 9,14, and 19, react in dimethylformamide in the presence of potassium carbonate with diaryl disulfides 2 to yield arylsulfenyl derivatives (3, 10, 15, 20). The arylthiolate anions 4 formed in this reaction can be oxidized by air to yield the starting disulfides 2 again. Tetraalkylthiuram disulfides 7 react in the same manner to yield dialkylaminothiocarbonylthio derivatives (8, 13, 18) of the title compounds. Oxidation of the arylsulfenyl derivatives with hydrogen peroxide in sodium hydroxide solution usually leads to sulfoxides (5, 11, 16), whereas oxidation with peracetic acid affords sulfones (6, 12, 17).
Asymmetric borane reduction of ketones catalyzed by N‐hydroxyalkyl‐l‐menthopyrazoles
Authors: Kashima Choji , Tsukamoto Yoshihiro , Higashide Kohei , Nakazono Hiroyuki 
Published: March 2009

AbstractThe equimolar mixture of N‐(hydroxyalkyl)pyrazoles and borane formed boric ester complex, in which the remaining borane was stabilized by the adjacent nitrogen of thr pyrazole ring. The borane complex derived from the chiral pyrazoles such as 3‐phenyl‐l‐menthopyrazole reduced p‐methylacetophenone (21) enantioselectively. When (2′S)‐2‐(2′‐phenyl‐2′‐hydroxyethyl)‐3‐phenyl‐l‐menthopyrazole ((2′S)‐10b) was used, 21 was reduced into (S)‐p‐methylphenyl‐1‐ethanol (22) in moderate chemical and optical yields. Due to the inconvenience of the preparation and the lower optical yield, the use of N‐(α‐hydroxyalkyl)pyrazoles was unpromising for the enantioselective reduction of ketones by borane.
Synthesis of 5,6‐dihydro‐2‐trifluoromethyl‐1,4‐dioxin‐3‐carboxanilides through polymer‐bound activated ester: Construction of dihydro‐1,4‐dioxin
Authors: Mah Heduck , Chang Kee Hyuk , Nam Kee Dal , Hahn Hoh‐Gyu , Bae Su Yeoul 
Published: March 2009

AbstractA new construction of dihydro‐1,4‐dioxin and a synthesis of 5,6‐dihydro‐2‐trifluoromethyl‐1,4‐dioxin‐3‐carboxanilides 22 through polymer‐bound activated ester are described. An intermediate β‐hydroxy ether 18 was prepared from the substitution reaction of α‐thio‐α‐chloro compound 8 with ethylene glycol followed by treatment with Raney Ni. Replacement of hydroxy by chlorine and then dehydrochlorination afforded trifluoromethyl dihydro‐1,4‐dioxin ester 15. The polymer‐bound trifluoromethyl dihydro‐1,4‐dioxin‐3‐carboxylic acid, 4‐hydroxy‐3‐nitrobenzophenone ester (21) was prepared through the reaction of polystyrene‐bound 4‐hydroxy‐3‐nitrobenzophenone (19) with the trifluoromethyl dihydro‐1,4‐dioxin‐3‐carbonyl chloride (20). Refluxing of 21 with substituted aniline in acetonitrile gave the corresponding carboxanilide 22. The reaction rate depended on the nucleophilicity of nitrogen of the aniline.
Syntheses of 2‐alkylthio‐1‐[4‐(N‐α‐ethoxycarbonylbenzyl)‐aminobenzyl]‐5‐hydroxymethylimidazoles
Authors: Shafiee A. , Hadizadeh F. , Noori S. B. 
Published: March 2009

AbstractStarting from the readily available p‐nitrobenzylamine a series of 2‐Alkylthio‐1‐[4‐(N‐α‐ethoxycarbonylbenzyl)aminobenzyl]‐5‐hydroxymethylirnidazoles were prepared.
Synthesis of new methylated thieno[2,3‐a] and [3,2‐b]carbazoles by reductive cyclization of 6‐(2′‐Nitrophenyl)benzo[b]thiophenes obtained by palladium‐catalyzed cross‐coupling isabel
Authors: Ferreira C. F. R. , Queiroz Maria‐João R. P. , Kirsch Gilbert 
Published: March 2009

AbstractThe synthesis of new methylated thieno[2,3‐a] and [3,2‐b]carbazoles (5) (R=H) was achieved by a palladium‐catalyzed cross‐coupling, intramolecular reductive cyclization sequence of reactions. The cyclization precursors 6‐(2′‐nitrophenyl)benzo[b]thiophenes (3) were obtained by Suzuki cross‐coupling of 6‐boronated methylbenzo[b]thiophenes intermediates (2) with 2‐bromo or iodonitrobenzene. The boronated intermediates (2) were prepared via bromine‐lithium exchange followed by boron transmetalation and coupled in situ using Pd(OAc)2 giving thus a “one‐pot” three steps reaction from the 6‐bromobenzo[b]thio‐phenes (1) to the cyclization precursors (3). In the reductive cyclization step, N‐ethylthienocarbazoles (5) (R=Et) were also obtained. Several experiments have been made varying the amount of triethylphosphite and the time of reaction, to avoid their formation.
Kinetic and thermodynamic control in the cyclization via thiiranium ions. Stereoselective synthesis of a 2,3,5‐trisubstituted tetrahydropyran ring
Authors: Gruttadauria Michelangelo , Noto Renato 
Published: March 2009

AbstractThe stereoselective rearrangement of tetrahydrofuran or tetrahydropyran rings having a phenylsulfanyl group in an exo position, via the intermediate thiiranium ions, is reported. The 5‐ or 6‐exo‐tet cyclization of hydroxy sulfides gave the kinetic products while the 6‐endo‐tet or 5‐endo‐tet gave the thermodynamic products. The rearrangement of the 5‐exo product to the 6‐endo‐ one is an interesting way for the stereoselective synthesis of substituted tetrahydropyrans.
A short synthesis of the parp inhibitor 2‐(4‐trifluoro‐methylphenyl)benzimidazole‐4‐carboxamide (NU1077)
Authors: Austen Steven C. , Kane John M. 
Published: March 2009

AbstractA four‐step synthesis of the PARP inhibitor 2‐(4‐trifluoromethylphenyl)benzimidazole‐4‐carboxamide (1, NU1077) is presented. Condensation of 2,3‐diaminotoluene and 4‐trifluoromethylbenzaldehyde afforded 4‐methyl‐2‐(4‐trifluoromethylphenyl)benzimidazole. Oxidation of the methyl group with potassium permanganate in warm t‐butanol afforded the carboxylic acid that was converted to the corresponding carboxamide via,/ the acid chloride.
Sythesis of methylthiomaleimides for the preparation of pyridazines and related comopounds
Authors: Tominaga Yoshionori , Shigemitsu Yasuhiro , Sasaki Kejni 
Published: March 2009

AbstractNew functionalized maleimides (3‐methylthio‐2,5‐dioxo‐1H‐pyrroles) were obtained by the reaction of ketene dithioacetals with nitromethane or the reaction of nitro ketene dithioacetal with active methylene compounds in the presence of the appropriate base in dimethyl sulfoxide followed by treatment with methanol.These nakeunudes reacted with various nucleophilic reagents such as election‐rich aromatic and heteroaromatic compounds like dialkylanilines, aminophenols, indoles, indolizines, and cyalazines to give the corresponding 3‐aryl‐ or heteroaryl‐ 1H‐pyrole‐2,5‐diones. Styryl and merocyanie dyes, and polycyclic pyridazine‐diones as chemiluminophors and succinimides were also obtained from these maleimides with good results.
Thermolytic ring closure reactions of 4‐azido‐3‐phenylsulfanyl‐and 4‐azido‐3‐phenylsulfonyl‐2‐quinolones to 12H‐quinolino‐[3,4‐b][1,4]benzothiazin‐6(5H)‐ones
Authors: Täubl Anna E. , Langhans Klaus , Kappe Thomas , Stadlbauer Wolfgang 
Published: March 2009

Abstract4‐Hydroxy‐3‐phenylsulfanyl‐2‐quinolones 2 and 4‐hydroxy‐3‐sulfonyl‐2‐quinolones 7, which are readily accessible from 4‐hydroxy‐2‐quinolones 1 and diphenyldisulfide or thiophenol, can be converted to 4‐azido‐3‐phenylsulfanyl‐2‐quinolones 10 or 4‐azido‐3‐phenylsulfonyl‐2‐quinolones 12 via 4‐chloro‐3‐phenylsul‐fanyl‐2‐quinolones 5 or 4‐chloro‐3‐phenylsulfonyl‐2‐quinolones 9, respectively. Thermolysis of the azides 10 and 12 results in a cyclization reaction to give quinolino[3,4‐b][1,4]benzothiazinone 11 and quino‐lino[3,4‐b][1,4]benzothiazinone dioxides 13, respectively. The conditions for thermolysis have been studied by differential scanning calorimetry (DSC).
A one‐pot synthesis of 2‐aryl‐2,3‐dihydro‐4(lH)‐quinazolinones by use of samarium iodide
Authors: Cai Guoping , Xu Xiaoliang , Li Zhifang , Lu Ping , Weber William P. 
Published: March 2009

Abstract2‐Aryl‐2,3‐dihydro‐4(lH)‐quinazolines have been prepared in a one‐pot synthesis by samarium idoide (SmI2) promoted reaction of o‐nitrobenzamide and aldehydes.
Synthesis and spectral properties of 2‐methylthio‐3H‐7‐[(o‐; m‐ and p‐substituted)phenoxy]‐4‐(p‐substituted‐phenyl)‐[1,5]benzodiazepines
Authors: Cortés Eduardo Cortés , Romero Cristina A. Cortés , Mellado Olivia García 
Published: March 2009

AbstractA series of eleven new 2‐methylthio‐3H‐7‐[(o‐; m‐ and p‐substituted) phenoxy]‐4‐(p‐substituted‐phenyl)‐[1,5]benzodiazepines, which have potentially useful pharmacological activities, has been synthesized by condensing the 4‐[(o‐; m‐ and p‐R1)phenoxy]‐1,2‐phenylendiamines with 3,3‐dimercapto‐1‐(p‐R2‐phenyl)‐2‐propen‐1‐one. Afterward the lH‐[1,5]benzodiazepine‐2‐thiones obtained were treated with sodium hydride and methyl iodide. The structure of all products was corroborated by ir, 1H nmr, 13C nmr and ms.
Synthesis of 3‐aroyl‐4‐(3‐chromonyl)‐2‐pyrazolines
Authors: Lévai Albert , Jekö József 
Published: March 2009

AbstractNew 3‐aroyl‐4‐(3‐chromonyl)‐2‐pyrazolines have been synthesized by the reaction of 3‐(3‐aryl‐3‐oxo‐propenyl)chromen‐4‐ones and diazomethane. Some of these 2‐pyrazolines have also been N‐acylated with a mixture of anhydrous pyridine and acetic anhydride or propionic anhydride. Structures of all new compounds have been elucidated by elemental analyses, mass spectrometry, ir and nmr spectroscopic measurements.
Application of the randomly optimized RDSQC experiment for the elucidation of an unknown compound
Authors: Hadden Chad E. 
Published: March 2009

AbstractThe application of the randomly optimized RDSQC (Randomly optimized Direct correlation Single Quantum Coherence) experiment for the detection of direct correlations facilitated the characterization of an unknown compound. The expected structure consisted of purely aliphatic moieties. The actual, identified compound contained the desired structure plus an adenosine functionality with two protons whose direct proton‐carbon couplings were over 200 Hz. Application of a 130 Hz optimized direct heteronuclear GHSQC experiment afforded no correlations for the adenine responses. The RDSQC experiment allowed for the simultaneous optimization of multiple couplings in a range of 130 to 220 Hz producing a direct correlation spectrum with all the expected responses.
Studies towards the synthesis of the benzodiazepine alkaloid auranthine
Authors: Witt Anette , Gustavsson Annika , Bergan Jan 
Published: March 2009

AbstractDifferent approaches towards the synthesis of auranthine have been investigated. A completed synthesis of 3‐[2‐(4‐oxo‐3,4‐dihydro‐quinazolin‐2‐yl)‐3,4‐dihydro‐1H‐benzo[e][1,4]‐diazepine‐2,5‐dione, an auranthine precursor, which after dehydration with 50% propylphophonic acid anhydride solution in ethl acetate and DMA gave a C‐acetyl derivative of aurnathine. Additionally studies towards the synthesis of fused quinazolinones yielded the C‐acetylated pyrido[2,1‐b]quinazolinones or butyric acid derivatives.
Synthesis of dihydrofuran rings using α‐substituted β‐ketoamides
Authors: Stefani Héalio A. , Silva Diogo O. , Costa Iguatemi M. , Petragnani Nicola 
Published: March 2009

AbstractIn this paper is described an unreported method employing α‐alkenyl β‐ketoamides as starting material to give 2,3‐dihydrofurans, precursors of substituted furans.
Cyclization of thiohydrazonate esters and azo‐hydrazone tautomerism of 2‐arylhydrazono‐3‐oxo‐1,4‐benzothiazines
Authors: Shawali Ahmad S. , Elsheikh Said , Párkányi Cyril 
Published: March 2009

AbstractReaction of ethyl arylhydrazonochloroacetates (1) with 2‐aminothiophenol (2) in ethanol in the presence of triethylamine yielded the respective ethyl thiohydrazonate esters (3). Similarly, methyl arylhydrazonochloroacetates (6) gave the corresponding methyl thiohydrazonate esters (7). Treatment of both 3 and 7 with hydrogen chloride in ethanol afforded the respective 1,4‐benzothiazine derivatives 4. Identical products (4) were obtained by refluxing 1 or 6 in ethanol in the presence of triethylamine. The structure of 4 was confirmed by their alternate synthesis starting with diethyl chloromalonate in ethanol in the presence of triethylamine which yielded the intermediate 1,4‐benzothiazine derivatives 8. The subsequent coupling of 8 with diazotized anilines in ethanol in the presence of potassium hydroxide afforded 4.
Decarboxylation in the synthesis of 4‐alkyl‐, 4‐alkenyl‐ and 4‐acylpyrimidines
Authors: Herstad Gunnar , Benneche Tore 
Published: March 2009

AbstractDecarboxylation of allylic esters of 4‐carboxypyrimidines in toluene at 111 °C in the presence of a Pd(0) catalyst, gives a mixture of a 4‐alkenylpyrimidine and a pyrimidine unsubstituted in the 4‐position. If the decarboxylation is carried out in the presence of benzaldehyde, then benzaldehyde is added to the 4‐position. Decarboxylation of 4‐carboxypyrimidines in the presence of different electrophiles, results in incorporation of the electrophile into the 4‐position together with a pyrimidine unsubstituted in the 4‐position. Use of microwave irradiation enhances the rate of the decarboxylations.
Enaminones as building blocks in organic synthesis: A novel route to polyfunctionally substituted benzonitriles, pyridines, eneylbenzotriazoles and diazepines
Authors: Hassanien Abu Zeid A. , Ghozlan Said A. S. , Elnagdi Mohamed H. 
Published: March 2009

AbstractAn efficient synthesis of enaminones 1a‐c is reported. Compounds 1a‐c reacted with diefhyl‐3‐amino‐2‐cyanopenten‐1,5‐dicarboxylate (3) to yield the benzonitriles 6. On the other hand, the reaction of la‐c with 3‐amino‐2‐cyano‐2‐pentene dinitrile (7) afforded a mixture of benzonitriles 10 and pyridines 9. The reaction of la‐c with 3‐aminocrotononitrile 11 has afforded the 4‐substituted‐3‐cyano‐2‐methylpyridines 15a‐c. The reaction of ethylene diamine with la‐c afforded 5‐substituted‐2,3‐dihydro‐lH‐[1,4]diazepines 18a‐c. On the other hand, la‐c reacted with o‐phenylenediamine to yield the 4‐(2‐aminopheynlamino)‐substituted enaminones 21. Compounds 21 could be converted into the benzotriazolylenones 22 on treatment with sodium nitrite in acetic acid solution.
Synthesis and biological effects of new derivatives of azines incorporating coumarin
Authors: Al‐Omran Fatima , Elassar Abdel‐Zaher A. , El‐Khair Adel Abou 
Published: March 2009

AbstractNew synthetic routes for triazolopyridine, pyridopyrimidine, pyridotriazine, imidazopyridine and pyri‐dazine derivatives incorporating a coumarin moiety with interesting biological activities are reported. Reactions of the 2‐oxo‐4‐(2‐dimethylaminoethenyl)‐2H‐chromene‐3‐carbonitrile (4) and 2‐amino‐4‐(2‐dimethylaminoethenyl)quinoline‐3‐carbonitrile (5) with benzotriazol‐1‐yl‐acetic acid hydrazide (6) affords the substituted [1,2,4]triazolo[1,5‐a]pyrido[3,4‐c]coumarines 9 and quinoline 12, respectively. Treatment of 4 with 2‐amino‐pyridine, glycine, urea, 3‐aminocrotononitrile or cyanothioacetamide affords 14–18, respectively. Treatment of 3‐amino‐3,4‐dihydro‐4‐imino‐chromeno[3,4‐c]pyridin‐5‐one (10) with α‐chloro‐acetylacetone affords pyridotriazine derivative 21. Compound 4 was also coupled with benzenediazonium chloride to afford 2‐oxo‐4‐[2‐oxo‐1‐(phenyl‐hydrazono)‐ethyl]‐2H‐chromene‐3‐carbonitrile 25. Treatment of the latter product with malononitrile afforded the 1‐phenyl‐3‐(3′‐Cyano‐2′‐oxo‐coumarin‐4′‐yl)‐6‐oxo‐pyridazine‐5‐carbonitrile (27). The structures of the newly synthesized compounds have been established on the basis of analytical and spectral data.
Synthesis of novel benzo[h] [1,6]naphthyridines via a rearrangement of hexahydro‐5H‐pyrrolo [2,1 ‐c] [1,4]benzodiazepines
Authors: Hinschberger Antoine , Fabis Frédéric , Santos Jana Sopkova‐De Oliveira , Rault Sylvain 
Published: March 2009

AbstractHeating of hexahydro‐5H‐pyrrolo[2,1‐c][1,4]benzodiazepine‐2,5,11‐trione in boiling phosphoryl chloride led to a rearranged product like 3,5‐dichlorobenzo[h][1,6]naphthyridine. This structure was established from X‐ray diffraction analysis.
Efficient synthesis of bromocyclopenta[b] indoles via a bromination ‐ reduction sequence
Authors: Lachance Nicolas , Chan Wing Yan 
Published: March 2009

AbstractSubstituted cyclopenta[b]indoles are selectively brominated in good yields with excess pyridine ‐ Br2 charge‐transfer complex (PyBr2) in a one‐pot reaction to provide 5 and/or 7‐bromoindoles. The mechanism involves the formation of an adduct (addition of bromine on the central double bond) which is subsequently reduced in situ with Zn and AcOH. A variety of functional groups in the cyclopentyl and the benzenoid rings are tolerated.
Synthesis anti‐fungal and anti‐bacterial screening of 3‐phenyl‐1,4,5‐trihydro‐pyrazol and 2, 4‐dihydro[ 1,2,4]‐triazol‐3‐one derivatives of 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran
Authors: Mulwad V. V. , Shirodkar Jyoti M. 
Published: March 2009

Abstract4‐Hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐carboxaldehydes 2a‐d are prepared from 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyrans 1a‐d via the Vielsmeyer Haack reaction. The 4‐hydroxy‐2‐oxo‐3‐(3′oxo‐3′‐phenylprop‐1′‐enyl)‐2H‐1‐benzopyrans 3a‐d are obtained from 2a‐d via the Claisen reaction. Refluxing compounds 3a‐d with hydrazine hydrate gave the 3‐phenyl‐5‐(4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)‐1,4,5‐trihydropyra‐zols 4a‐d. Stirring compounds 2a‐d with semicarbazide hydrochloride in acidic medium gave the 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐aldehyde‐semicarbazone 5a‐d, which on cyclisation with ferric chloride hexahydrate gave the 5‐(4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)‐2,4‐dihydro[1,2,4]triazol‐3‐ones 6a‐d. All these compounds show significant antibacterial activities.