1403873-48-2Relevant articles and documents
A modular synthesis of polysubstituted indolizines
Kucukdisli, Murat,Opatz, Till
, p. 4555 - 4564 (2012/11/07)
The N-alkylation of pyridines with cyanohydrin triflates or α-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. Polysubstituted indolizines were synthesized through [3+2] cycloaddition of nitroalkenes with pyridinium ylides. In contrast to previous reports of 1,3-dipolar cycloadditions, in this work no electron-deficient groups remain in the products. Copyright