Deoxypegan-1-one derivatives. synthesis and borohydride reduction of 3-[(E)-arylmethylidene]-3,9-dihydropyrrolo[2,1-b]quinazolin-1(2H)-ones

3-[(E)-Arylmethylidene]-3,9-dihydropyrrolo[2,1-b]quinazolin-1(2H)-ones were prepared by reaction of quinazolyl-2-propionic acid hydrochloride with aromatic aldehydes in acetic anhydride in the presence of Et₃N. 3-[(E)-Arylmethylidene]-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-1-ols were formed by reduction of the 3-arylidene derivatives with sodium borohydride in methanol, readily lost water when heated with acids, and were converted into 3-[(E)-arylmethylidene]-3,9-dihydropyrrolo[2,1-b]quinazolines. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 463–467, September–October, 2006.     

Condensed isoquinolines 23. Reaction of <Emphasis Type="Italic">o</Emphasis>-bromomethylphenyl-acetonitrile with anthranilic acids: Synthesis of 6H, 12H,17H-dibenzo[3,4:6,7][1,8]-naphthyridino[1,8-<Emphasis Type="Italic">ab</Emphasis>]quinazoline-6,17-diones

The direction of the reaction of anthranilic acids with o-bromomethylphenylacetonitrile upon fusion depends on the temperature and nature of the substituent in the anthranilic acid. The reaction may lead to three types of products: Derivatives of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones below 150°C and to 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one or derivatives of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones above 150°C depending on the nature of the substituent in the anthranilic acid. A study was carried out on the mechanism for the formation of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones, which permitted the preparation of 6-(4-methylphenyl)-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1059–1067, July, 2007.     

Synthesis and Antitumor Activity of 5-Phenyl-1,3-thiazole-4-sulfonamide Derivatives

Russian Journal of General Chemistry - A method for the synthesis of 5-phenyl-1,3-thiazole-4-sulfonyl chloride was developed based on the cyclization of ethyl...     

Synthesis of diarylazolo[<Emphasis Type="Italic">a</Emphasis>]pyridines from [(<Emphasis Type="Italic">Z</Emphasis>)-2,4-diaryl-4-oxo-2-butenyl]azolium salts

A method for the synthesis of derivatives of [1, 3]thiazolo[3,2-a]pyridines, pyrido[2,1-b][1, 3]benzo-thiazole, [1, 3, 4]thiadiazolo[3,2-a]pyridine, and [1, 2, 4]triazolo[4,3-a]pyridine, which includes base initiated cyclization of quaternary azolium salts, formed by the interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-alkyl-1H-1,2,4-triazoles, 4-methyl-1,3-thiazole, 1,3-benzothiazole, and N-phenyl-1,3,4-thiadiazole-2-amine. Derivatives of 2-chloroimidazo[1,2-a]pyridine were obtained when 5-chloro-1-methyl-1H-imidazole was used.     

Dealkylation of quaternary 1-alkylazolo[a]pyridinium salts

A convenient method is proposed for the preparation of new derivatives of free heterocyclic bases of imidazo[1,2-a]pyridine, pyrido[1,2-a]benzimidazole, and [1,2,4]triazolo[4,3-a]pyridine series. This method entails the dealkylation of N-(2-cyanoethyl)- or N-benzylazolopyridinium quaternary salts in the presence of bases and reaction with ammonium formate in the presence of Pd/C, respectively.     

Condensed isoquinolines. Part 6. Synthesis of 5-aryl-7,12-dihydroisoquino[2,3-a]quinazolinium salts

2-(o-Aroyl)phenyl-1, 4-dihydroisoquinolin-3(2H)-imine hydrobromides have been synthesized by the reaction of o-bromomethylphenylacetonitrile with o-aminobenzophenones. The products were cyclized into 5-aryl-7,12-dihydroisoquino[2,3-a]quinazolinium perhclorates.T. G. Shevchenko University, Kiev 252017. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 664–666, May, 1995. Original article submitted April 15, 1995.     

3-(Hetarylamino)- and 3-[(hetarylmethyl)amino]-isoquinolin-1(2H)-ones

The reaction of 2-(cyanomethyl)benzoic acid with amines RNH₂ (R = Ar, Het, CH₂Ar, CH₂Het) leads to the formation of the corresponding 3-NHR-isoquinolin-1(2H)-ones. When R = CH₂Ar and CH₂Het, there is a side reaction involving hydrolysis of the hydrolytically-unstable intermediates, derivatives of 2-(2-amino-2-iminoethyl)benzoic acid, leading to 2-R-isoquinoline-1,3(2H,4H)-diones.     

Interaction of (z)-4-bromo-1,3-di(2-thienyl)- 2-buten-1-one with amines,synthesis of di(2-thienyl)azolo[<Emphasis Type="Italic">a</Emphasis>]pyridines

(Z)-4-Bromo-1,3-di(2-thienyl)-2-buten-1-one was obtained by the bromination of 1,3-di(2-thienyl)-2-buten-1-one by NBS in anhydrous CCl₄. The starting butanone was obtained by the condensation of 1-(2-thienyl)-1-ethanone by the action of SOCl₂. The reaction of (Z)-4-bromo-1,3-di(2-thienyl)-2-buten-1-one with tertiary amines such as Et₃N, pyridine, 1-alkyl-1,3-diazole, 1-alkylbenzimidazole, and 1-alkyl-1,2,4-triazole leads to quaternary salts. The azolium salts cyclize by the action of base to give di(2-thienyl)azolo[a]pyridinium derivatives. 3-Methyl-6,8-di(2-thienyl)[1,3]thiazolo[3,2-a]pyridin-4-ium and 2,4-di(2-thienyl)pyrido[2,1-b]benzothiazol-10-ium bromides were obtained by the same procedure but without separating the intermediate quaternary salts.