One-pot synthesis of tri- and tetrasubstituted pyridines by sequential ring-opening/cyclization/oxidation of N-arylmethyl 3-aziridinylpropiolate esters

Abstract

A novel strategy for the one-pot synthesis of substituted pyridines from N-arylmethyl 3-aziridinylpropiolate esters is described. The method employs a three-step procedure including the formation of allenyl imines, phosphine-catalyzed cyclization, and subsequent oxidation of the dihydropyridines. Depending on the reaction conditions of the final oxidation step, tri- and tetrasubstituted pyridines can be selectively produced.

Keywords: cyclization; heterocycles; organocatalysis; small ring compounds; synthetic methods.