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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Synthesis of Substituted Imidazo[1,5-a]pyrimidines, 1H-pyrrolo[2,3- b]pyridines and 3-methyl-3H-imidazo[4,5-b]pyridines

Author(s): Jingshing Wu, Xuechao Xing and Gregory D. Cuny

Volume 6, Issue 3, 2009

Page: [203 - 207] Pages: 5

DOI: 10.2174/157017809787893000

Price: $65

Abstract

Cyclization of in situ generated 5-aminoimidazoles with various malondialdehydes or 1,3-diketones gave substituted imidazo[1,5-a]pyrimidines. However, cyclization of 2-aminopyrroles and 5-amino-1-methylimidazoles resulted in condensations on a carbon atom of the heterocyclic ring instead of nitrogen generating 1H-pyrrolo[2,3- b]pyridines (i.e. 7-azaindoles) and 3-methyl-3H-imidazo[4,5-b]pyridines, respectively. In these cases the addition of pyrrolidine to the reaction mixture after the initial condensation between the amino group and one of the carbonyl groups of the malondialdehydes or 1,3-diketones significantly increased the yields of 1H-pyrrolo[2,3-b]pyridines and 3-methyl- 3H-imidazo[4,5-b]pyridines.

Keywords: Imidazo[1,5-a]pyrimidines, 1H-pyrrolo[2,3-b]pyridines, 7-azaindoles, 3-methyl-3H-imidazo[4,5-b]pyridines, cyclization


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