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

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

Volume: 6 Issue: 3

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

Affiliation:

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

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.

Cite this article as:

Wu Jingshing, Xing Xuechao and Cuny D. Gregory, Synthesis of Substituted Imidazo[1,5-a]pyrimidines, 1H-pyrrolo[2,3- b]pyridines and 3-methyl-3H-imidazo[4,5-b]pyridines, Letters in Organic Chemistry 2009; 6 (3) . https://dx.doi.org/10.2174/157017809787893000