A Modular Synthesis of Polysubstituted Indolizines

作者:Kucukdisli Murat; Opatz Till*
来源:European Journal of Organic Chemistry, 2012, 2012(24): 4555-4564.
DOI:10.1002/ejoc.201200424

摘要

The N-alkylation of pyridines with cyanohydrin triflates or a-halonitriles furnishes 1-(1-cyanoalkyl)pyridinium salts that can react with nitroolefins under basic conditions to furnish polysubstituted indolizines. Overall, the indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products. When bromoacetonitrile was used for the N-alkylation, indolizine-3-carbonitriles were obtained instead. The pyridine component may be replaced by other azines, giving rise to related heterocyclic systems.

  • 出版日期2012-8