Synthesis of new 2,3-disubstituted pyridines containing a 1,2,3-triazole in the side-chain via one-pot copper-catalyzed azide-Alkyne cycloaddition

Abstract

A series of 1,2,3-triazole-containing pyridines has been synthesized using the Cu(II) catalyzed 'click approach' from sodium azide and corresponding halides. The synthesis involves the amidation of 2-Amino-3-hydroxypyridine with benzoyl chloride or cinnamic acid followed by reaction with propargyl bromide to obtain N-(3-(prop-2-ynyloxy)pyridin-2-yl)benzamide 5 and 3-phenyl-N-(3-(prop-2-ynyloxy)-pyridin-2-yl)acrylamide 10 respectively. These compounds underwent one-pot tandem copper-catalyzed azidation and CuAAC reactions to provide compounds 6a-h and 11a-g in moderate to good yields.