Halogenation of Imidazo[4,5-b]pyridin-2-one Derivatives

Autor:	N. N. Smolyar, S. V. Gres'ko, Kh. Ya. Lopatinskaya, Yu. M. Yutilov
Rok vydání:	2005
Předmět:	Iodine atom Acetic acid chemistry.chemical_compound Chemistry Organic Chemistry Chlorine Halogenation Organic chemistry chemistry.chemical_element General Medicine Medicinal chemistry
Zdroj:	ChemInform. 36
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200542166
Popis:	Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.
Databáze:	OpenAIRE
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