Investigations of Imidazoles. 101. Synthesis of 2,3-Dihydroimidazo[1,2-a]pyrimidine from 2-Aminopyrimidine

Two novel preparative methods have been developed for the synthesis of 2,3-dihydroimidazo[1,2-a]pyrimidine from 2-aminopyrimidine. These are the reaction with 1,2-dibromoethane and also the reaction with ethylene chloro(bromo)hydrin, subsequent treatment of 1--hydroxyethyl-2-imino-1,2-dihydropyrimidine with thionyl chloride, and cyclization of the intermediate 1--chloroethyl-2-imino-1,2-dihydropyrimidine in the presence of sodium hydroxide.     

Research in the imidazole series. 93. Synthesis of derivatives of benzimidazolyl-1-acetic acid

A simple method has been developed for obtaining esters of benzimidazolyl-1-acetic acid and its 2-alkyl (or aralkyl) derivatives, by reaction of benzimidazoles with esters of chloroacetic or bromoacetic acid in DMF in the presence of anhydrous potassium carbonate. The method of synthesis of amides of these acids has been simplified.For Communication 92, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 29, No. 5, pp. 656–658, May, 1993.     

Research in the imidazole series. 96. Reaction of 1-methyl-4-nitro-5-chlorimidazole with phenols, naphthols, and 8-hydroxyquinoline

By reactions of 1-methyl-4-nitro-5-chlorimidazole with 4-nitrophenol, - and -naphthols, and 8-hydroxyquinoline, a number of 1-methyl-4-nitro-5-aryl(heteryl)oxyimidazoles have been obtained. With aminophenols, under analogous conditions, 1-methyl-4-nitro-5-hydroxyphenylaminoimidazoles have been obtained.For Communication 95, see [1].Novokuznetsk Scientific-Research Chemical-Pharmaceutical Institute, Novokuznetsk 654034, Russia. Center for Medicinal Chemistry, All-Russian Scientific-Research Chemical-Pharmaceutical Institute, Moscow 119815. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 327–329, March, 1998.     

Investigations in the imidazole series

Imidazo[1,2-a]imidazole derivatives were synthesized by the reaction of 1-acylmethyl-2-bromo-4,5-diphenylimidazoles with ammonia and primary amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1243–1247, September, 1971.     

Studies in the imidazole series

The reaction of 2-mercaptobenzimidazole and 5, 6-dimethyl-2-mercaptobenzimidazole with -halogenoketones has given a series of 2--oxoalkylthio- and 2--oxoaralkylthiobenzimidazoles—intermediate products for the synthesis of thiazolo[3,2-a]benzimidazoles. The compounds obtained exhibit the phenomenon of ring-chain tautomerism.For part XXXV, see [6].     

Studies in the imidazole series

6,7-Dimethylbenzimidazo[2,1-b]thiazolid-3-one was synthesized, and its reactions with aldehydes, isatin, nitroso compounds, and arene diazonium salts were studied. As a result, ylidene and imino derivatives and azo coupling products were obtained. According to the IR spectra, the azo coupling products have 6,7-dimethylbenzimidazo[2,1-b]thiazolidine-2,3-dione 2-arylhydrazone structures.See [1] for communication LVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 822–825, June, 1971.     

Synthesis and some properties of 6-β-oxoalkyl(aralkyl,hetaralkyl, cycloalkyl)thiopurines

The reaction of 6-purinethione with -haloketones has given a series of new 6--oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines. Their alkylation in position 9 and acid hydrolysis to hypoxanthine and its 9-alkyl derivatives has been studied. The hydrolysis of the acetals of 6-formylmethylthiopurine and the oxidation of 6-(2,3-dihydroxypropyl)thiopurine leads to 6-formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-hydroxy-7,8-dihydrothiazolo[2,3-i]purine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1548–1553, November, 1993.     

Investigations in the imidazole series 97. Synthesis and some transformations of 5-nitro-5-hydroxyalkylamino- and 4-hydroxy-alkylamino-5-nitroimidazoles

A series of 1-alkyl(1,2-dialkyl)-substituted 4-nitro-5-hydroxyalkylamino- and 4-hydroxyalkylamino-5-nitro-imidazoles were obtained by the reaction of 1-alkyl(1,2-dialkyl)-substituted 4-nitro-5-chloro(bromo)imidazoles with amino alcohols. Their reactions with thionyl chloride and carboxylic acid halides and their catalytic hydrogenation were studied. For Communication 96, see [1]. Center of the Chemistry of Medicinal Agents, All-Russia Scientific-Research Chemical-Pharmaceutical Institute, Moscow 119815. Novokuznetsk Scientific-Research Chemical-Pharmaceutical Institute, Novokuznets 654034, Russia. Zaporozh'e State Medical University, Zaporozh'e 33074. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10. pp. 1346–1351, October, 1998.     

Investigations in the imidazole series

The reactions of 2-mercaptonaphth[1,2-d]imidazole with 1,2-dichloro- and 1,2-dibromoethanes and the cyclization of 3-(-hydroxyethyl)- and 2-(-hydroxyethyl)mercaptonaphth[1,2-d]imidazoles were studied. 2,3-Dihydro derivatives of naphth[1,2-d]imidazo[1,2-b]thiazole and naphth[1,2-d]imidazo[3,2-b]thiazole were obtained.See [1] for communication LXX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 257–259, February, 1972.