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, Gregory D. Cuny.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 3 , 2009

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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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Article Details

Year: 2009
Page: [203 - 207]
Pages: 5
DOI: 10.2174/157017809787893000
Price: $65

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