ChemInform Abstract: Reaction of 3-Acetonyl-5-cyano-1,2,4-thiadiazole with Phenylhydrazine Hydrochlorides: Indolization and Phenylpyrazolation

Autor:	Tsuneo Iwakawa, Akira Murabayashi, Giichi Sugimori, Hiroshi Nakai
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Reaction mechanism chemistry Hydrochloride Phenylhydrazine hydrochloride General Medicine Antimicrobial Medicinal chemistry Pyrrole derivatives Phenylhydrazine
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
Popis:	Treatment of 3-acetonyl-5-cyano-1, 2, 4-thiadiazole (1) with 4-methyl or 4-methoxyphenylhydrazine hydrochloride provided 5-cyano-3-(2, 5-dimethylindol-3-yl)-1, 2, 4-thiadiazole (2) or 5-cyano-3-(5-methoxy-2-methylindol-3-yl)-1, 2, 4-thiadiazole (3) as the sole product, respectively. In contrast, treatment of 1 with phenylhydrazine hydrochloride resulted in the formation of 5-cyano-3-(2-methylindol-3-yl)-1, 2, 4-thiadiazole (4) and the unexpected 5-cyano-3-(3, 5-dimethyl-1-phenylpyrazol-4-yl)-1, 2, 4-thiadiazole (5). In a similar manner, when 1 was treated with 4-chiorophenylhydrazine hydrochloride, indolization was suppressed by phenylpyrazolation giving rise to 5-cyano-3-(5-chloro-2-methylindol-3-yl)-1, 2, 4-thiadiazole (6) and 5-cyano-3-[1-(4-chlorophenyl)-3, 5-dimethylpyrazol-4-yl]-1, 2, 4-thiadiazole (7). The reaction mechanism is discussed. Compounds 4, 5 and 6 exhibited weak antimicrobial activity against Helicobacter pylori.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0d6915979b6f8451262c4e066124a485 https://doi.org/10.1002/chin.200025057 Zobrazit plný text záznamu Plný text