Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

Abstract

An efficient synthesis of multi-substituted pyridines and pyrroles from aryl methyl ketones with 1-amino-2-methylpropan-2-ol and 1,2-diamino-2-methylpropane, respectively, has been developed. The reactions each involved cleavage of one C–N bond and formation of two new bonds, namely a C–C bond and C–N bond, during an oxidative cyclization process promoted by I₂/PhNO₂. The C–N bond adjacent to the primary carbon of 1,2-diamino-2-methylpropane was the one selectively cleaved.