Ionic Liquid-Mediated Facile Synthesis and Antimicrobial Study of Thiazolo [2,3-b]Benzo[h]Quinazolines and Thiazino[2,3-b] Benzo-[h]Quinazolines

Abstract

8-Methoxy-4-phenyl-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione, obtained by the condensation of 2-benzylidene-6-methoxy-3,4-dihydronapthalene-1(2H)-one with thiourea, on reaction with chloroacetic acid and 3-chloropropanoic acid in the presence of the ionic liquid N-methylpyridinium tosylate furnishes 3-methoxy-7-phenyl-7,10-dihydro-5H- benzo[h]thiazolo[2,3-b]quinazoline-9(6H)-one and 3-methoxy-7-phenyl-5,6,10,11-tetrahydro- benzo[h][1,3]thiazino[2,3-b]quinazoline-9(7H)-one. Further, condensation of the thione with 1,2-dibromoethane and 1,3-dibromopropane yields 3-methoxy-7-phenyl-6,7,9,10-tetrahydro-5 H-benzo[h]thiazolo[2,3-b]quinazoline and 3-methoxy-7-phenyl-5,6,7,9,10,11-hexahydrobenzo [h][1,3]thiazino[2,3-b]quinazoline respectively. Arylidene derivatives have been obtained by two routes. The structures of the cyclized compounds have been established on the basis of elemental analysis and spectroscopic data. The synthesized compounds were screened for antimicrobial activity. Some of the compounds showed promising antimicrobial activities.     

Anthra[1,2-b]furan and 1h-naphth[2, 3-g]indole derivatives

A number of previously inaccessible anthra[1,2-b]furan and 1H-naphth[2,3-g]indole derivatives were obtained by condensation of 1,4-anthraquinone with acetoacetic ester and its analogs. Quinones of the anthra[1,2-b]furan series were obtained by oxidation of the methoxy derivatives of anthra[1,2-b]furan.Translated from Khimiya Geterotsiklicheskikh Soedtaenii, No. 8, pp. 1027–1029, August, 1972.     

Condensed pyridine bases. A new approach to the synthesis of 3-phenacylbenzo[b]thiophenes and 3-phenacyl-5-ethylthieno[2,3-b]thiophene. Synthesis of new derivatives of benzothieno[2,3-c]pyrylium and thieno[2′,3′:5,4]thieno-[2,3-c]pyrylium and pyridine bases

A new method is proposed for the production of substituted 3-phenacylbenzo[b]thiophenes by the intramolecular cyclization of 1-phenyl-4-phenylthio-1,3-butanediones in polyphosphoric acid. The analogous cyclization of 1-phenyl-4-(5-ethyl-2-thienylthio)-1,3-butanedione leads to 3-phenacyl-5-ethylthieno[2,3-b]thiophene. The acylation of substituted 3-phenacylbenzo[b]thiophenes and 3-phenacyl-5-ethylthieno[2,3-b]thiophene by the anhydrides of aliphatic acids in the presence of perchloric acid leads to 1-alkyl-3-phenylbenzothieno[2,3-c]pyrylium perchlorates and 2-ethyl-5-phenyl-7-methylthieno[2′,3′:5,4]thieno[2,3-c]pyrylium perchlorate. The action of ammonium acetate on the obtained salts gives the corresponding pyridine bases. L. M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 340114. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1335–1339, October, 1998.     

Polymethine dyes — Benzofuro[2,3-b]pyridine and selenonaphtheno[2,3-b]pyridine derivatives

Polymethine dyes — benzofuro[2,3-b]pyridine and selenonaphtheno[2,3-b]pyridine derivatives — were synthesized, and their spectral properties are discussed. Replacement of a vinylene group by an oxygen or selenium atom in one benzene ring of the 2-benzo[h]quinoline residue in the cyanines causes a large bathochromic shift of the absorption maxima of the dyes as compared with replacement by a sulfur atom. The dyes derived from benzofuro[2,3-b]pyridine derivatives are more deeply colored than the derivatives of both thionaphtheno[2,3-b]-pyridine and selenonaphtheno[2,3-b]pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp.1611–1614, December, 1972.     

Nitrogen and sulfur heterocycles. 45. Dual reactivity of 1,2-dioxo-3a-alkyl-7-chloroimidazolidino[3,2-f]-pyrido[2,3-b]-1,4-thiazines

1,2-Dioxo-3a-alkyl-7-chloroimidazolidino[3,2-f]pyrido[2,3-b]-1,4-thiazines react with o- and p-nitroanilines, alkyl and acyl halides, and heterocyclic amines to give C₍₂₎- and N₍₃₎-substituted 3a-alkyl-7-chloroimidazolidino[3,2-f]pyridol[2,3-b]-1,4-thiazines.For Communication 44, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1688–1693, December, 1987.     

Facile and convenient synthesis of new thieno[2,3-b]-thiophene derivatives

A facile and convenient synthesis of bis(2-(1H-benzo[d]imidazol-2(3H)-ylidene)-3-oxopropanenitrile), bis((3-amino-5-(methylthio)-1H-pyrazol-4-yl)methanone) and bis(2-thioxo-1,2-dihydropyrimidine-5-carbonitrile) derivatives incorporating a thieno- [2,3-b]thiophene moiety via versatile, readily accessible diethyl 3,4-dimethylthieno-[2,3-b]thiophene-2,5-dicarboxylate is described.     

Efficient synthesis of fused perhydrofuro[2,3-b]pyrans (and furans) by ring opening of 1,2-cyclopropanated sugar derivatives

[structure: see text]. An efficient method has been developed for the construction of fused perhydrofuro[2,3-b]pyrans by diastereoselective ring opening of 1,2-cyclopropanated sugar derivatives. The methodology has been successfully applied to the synthesis of fused perhydrofuro[2,3-b]pyrano-gamma-butyrolactone derivatives.     

One-pot synthesis of imidazo[1,2-b]pyrazole,imidazo[1,2-b]-1,2,4-triazole,imidazo[1,2-a]pyridine,imidazo[1,2-a]pyrimidine,imidazo[1,2-a]benzimidazole,and 1,2,4-triazolo[4,3-a]benzimidazole derivatives

Hydrazonoyl bromides 1a-c react with 5-amino-3-phenyl-1H-pyrazole, 5-amino-1H-1,2,4-triazole, 2-aminopyridine, and 2-aminobenzimidazole to afford the corresponding imidazol[1,2-b]pyrazoles 10, imidazo[1,2-b]-1,2,4-triazoles 11, imidazo[1,2-a]pyridines 16, imidazo[1,2-a]pyrimidines 17, and imidazo[1,2-a]benzimidazoles 20, respectively. Compounds 1a-c reacted also with 2-methylthiobenzimidazole to give 1,2,4-triazolo[4,3-a]benzimidazole derivatives 21. © 1997 John Wiley & Sons, Inc.     

3-炔基咪唑并[1,2-b]哒嗪的简便合成

以咪唑并[1,2-b]哒嗪为原料,与N-碘代丁二酰亚胺在三氟乙酸/二氯甲烷中于室温进行碘代反应制得3-碘咪唑并[1,2-b]哒嗪(3);3与三甲基硅基乙炔在Pd(OAc)_2催化下经Sonogashira偶联反应制得3-三甲基硅基乙炔基咪唑并[1,2-b]哒嗪(4);4在碳酸钾作用下脱除三甲基硅基合成了3-炔基咪唑并[1,2-b]哒嗪,总收率61.2%,其结构经~1H NMR和HR-MS确证。     

Synthesis of fluorantheno[1,2-b]thiophene and fluorantheno[3,2-b]thiophene,isosteres of benzofluoranthenes

The total syntheses of fluorantheno[1,2-b]thiophene and fluorantheno[3,2-b]thiophene are reported. The common cyclobutanone intermediate which was obtained by [2 + 2] addition of fluorenylidene ketene with 2,3-dihydrothiophene underwent regioselectively α or β ring opening to lead to linear or angular PAC skeleton molecules under desired conditions. 2,3-Dichloro-5,6-dicyanobenzoquinone was applied for aromatization to achieve the formation of PAC's. These two isosteres exhibit very similar uv/visible spectra to benzo[a] and [b]fluoranthenes respectively. Spectroscopic data used for their structural assignments is also discussed.     

Investigation of heterocycles containing nitrogen or sulfur. 47. Reactions of 1,2-dioxo-3a-alkyl-4,7-dichloroxazolidino [3,2-f]pyrido[2,3-b]-1,4-thiazines with saturated cyclic amines. synthesis and structure of derivatives of 1,2-dihydrothiazolo[5,4-b]pyridine

It has been established spectroscopically that 1-N-oxalamides of 2-acyl-5-chloro-1,2-dihydrothiazolo[5,4-b] pyridine are formed in the reaction of 4,7-dichloroxazolidino[3,2-f]pyrido[2,3-b]-1,4-thiazines with morpholine, piperidine and pyrrolidine. The products are a mixture of amide conformers in solution. The reaction intermediate 2-(1-chloro-2-oxobutylthio)-3-pyrrolidinooxamoyl-6-chloropyridine has been isolated and characterized. A proposed reaction scheme is presented.For Communication 46 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1125–1132, August, 1993.     

Synthesis of 6-methylfuro[2,3-b]pyridine

The Claisen condensation of ethyl 2-ethoxy-6-methylpyridine-3-carboxylate with ethyl acetate gave ethyl 2-ethoxy-6-methylnicotinoylacetate, which was converted to 3-bromo-acetyl-6-niethyl-2-pyridone by heating with bromine in 48% hydrobromic acid. The cyclization of the bromoacetylpyridone by the action of silver oxide in methanol gave 3-oxo-6-methyl-2,3-dihydrofuro[2,3-b]pyridine, which was reduced to 3-hydroxy-6-methyl-2,3-dihydrofuro[2,3-b]pyridine with lithium aluminum hydride in dimethoxyethane. Acetylation of the latter gave its acetate, the pyrolysis of which in vacuo gave 6-methylfuro[2,3-b]-pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1544–1546, November, 1972.     

Thermolyzed products of naphth[1,2-d]imidazo[2,1-b]-thiazole-2,3-dione

Themolysis of naphth[1,2-d]imidazo[2,1-b]thiazole-2,3-dione ( 1 ) in dimethylformamide gave an intermediate 2-isocyanatonaphtho[1,2-d]thiazole ( 2 ), which underwent [4 + 4] cyclodimerization to yield dinaphtho-[1″,2″:4,5;1′″,2′″:4′,5′]dithiazolo[3,2-a:3′,2′-e]-1,3,5,7-tetrazocine-9,19-dione ( 3 ). The possible [4 + 2] cycloadduct, 3-(2-naphtho-[1,2-d]-thiazolyl)naphtho[1′,2′:4,5]thiazolo[3,2-a]-1,3,5-triazine-2,4-dione ( 4 ), an usual dimer type of heterocyclic isocyanates was not produced. Discrimination between the two isomers was established on the basis of spectral analyses.     

Crystal or low molecular mass organogel based on sugar-derived chiral pyrano[2,3-b]naphtho[1,2-e]pyrans

[structure: see text] 2-C-Acetoxymethyl glycal derivatives reacted with beta-naphthol in the presence of InCl(3) (30 mol %) to give chiral pyrano[2,3-b]naphtho[1,2-e]pyrans in good to excellent yields via stereoselective Ferrier rearrangement-tandem cyclization. The major glucose-derived product exhibited crystal packing with C-H...O and C-H...pi (arene) interactions and the major galactose-derived product, a low molecular mass organogelator (LMOG), formed a rare type of micro tubular gel assembly in n-hexane.     

Benzo[3,4]cyclobuta[1,2-b]thiophene

Tye synthesis of thieno[3,2-c]cinnoline is described; vapour phase thermolysis of this compound gives benzo[3,4]cyclobuta[1,2-b]thiophene.     

Endo-selective quenching of hexahydropyrrolo[2,3-b]indole-based N-acyliminium ions

Radical decarboxylation of L-tryptophan-derived (2S,3aR,8aS)-8-arylsulfonyl-1,2-di(methoxycarbonyl)-1,2,3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indoles 8 and 9 in the presence of diphenyl diselenide results in the endo-selective formation of (2R,3aR,8aS)-8-arylsulfonyl-1-methoxycarbonyl-2-phenylselenyl-1,2,3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indoles 10 and 11. These selenides, in conjunction with Lewis acids, serves as precursors to the corresponding N-acyl iminium ions, which undergo selective endo-face quenching by allyltributylstannane, allyltrimethylsilane, propargyltrimethylsilane, and trimethylsilylcyanide. Stereochemical assignments rest on NMR data and crystallographic studies. The endo-selective nature of these reactions is interpreted in terms of minimization of allylic strain at the transition state for nucleophilic attack on the N-acyl iminum ion.     

Reduction and alkaline hydrolysis of 5-oxoindeno[1,2-b]pyridinium salts

5,9b-Dihydro derivatives of indeno[1,2-b]pyridine were obtained by the reduction of the corresponding 1,2-dimethyl-4-aryl-5-oxoindeno[1,2-b]pyridinium perchlorates. 1,2-Dimethyl-3-ethoxycarbonyl-4-phenyl-5-oxoindeno[1,2-b]pyridinium perchlorate forms in alkaline medium with splitting, recyclization and deamination products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp 86–89, January, 1987.     

Synthesis of thieno[2,3-d]thia[1]pyrano[4,3-b]pyrrole derivatives

It is shown that 2-methyl-3-carbethoxy-4H,8H,5,6-dihydrothieno[2,3-d]thia[1]pyrano [4,3-b]pyrrole and 8-methyl-9-carbethoxy-10H,5,6-dihydrothieno[2,3-d]thia[1]chromeno[4,3-b]pyrrole and their S,S-dioxides, respectively, are obtained in the reaction of 2-methyl-3-carbethoxy-4-thienylhydrazine with tetrahydro-4-thiopyrone, tetrahydro-4-thiopyrone S, S-dioxide, 4-thiochromanone, and 4-thiochromanone S,S-dioxide in the presence of an acid catalyst.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 195–196, February, 1979.     

Synthesis of 3-methyl-7-phenylimidazo-[1,2-b]-1,2,4-triazine

The bromocyclization of 3-allylamino-5-phenyl-1,2,4-triazine gives 3-bromomethyl-7-phenyl-2,3-dibromo-1H-imidazo[1,2-b]-1,2,4-triazinium bromide, which is transformed into 3-methyl-7-phenylimidazo-[1,2-b]-1,2,4-triazine.Yekaterinburg Fire-Fighting Technical Institute, Ministry of Internal Affairs, Russian Federation, 620002 Yekaterinburg. Chelyabinsk State University, 454136 Chelyabinsk. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 110–111, January, 1998.     

Synthesis of 2,3-dioxo-2,3-dihydro-4-methyl-6-chloro-1H-pyrrolo[2,3-b]pyridine and its 1-α-L-arabinopyranoside

A new type of isatin analog-2,3-dioxo-2,3-dihydro-4-methyl-6-chloro-1H-pyrrolo[2,3-b]pyridine — was obtained by oxidation of 4-methyl-6-chloro-1H-pyrrolo(2,3-b]pyridine. Condensation of L-arabinose with 4-methyl-6-chloro-2,3-dihydropyrrolo[2,3-b]pyridine and subsequent acetylation and dehydrogenation gave 1-(2,3,4-tri-O-acetyl--L-arabinopyranosyl)-4-methyl-6-chloropyrrolo[2,3-b]pyridine, which served as the starting compound for the synthesis of 1--L-arabinopyranosyl-4-methyl-6-chloropyrrolo[2,3-b]pyridine. Oxidation of 1-(2,3,4-tri-O-acetyl-L-arabinopyranosyl)-4-methyl-6-chloropyrrolo[2,3-b]pyridine gave 1-(2,3.4-tri-O-acetyl--L-arabinopyranosyl)-2,3-dioxo-2,3-dihydro-4-methyl-6-chloropyrrolo [2,3-b]pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1083–1086, August, 1977.