Selectivity in domino reaction of ortho-carbonyl azides with malononitrile dimer leading to [1,2,3]triazolo[1,5-a]pyrimidines

Abstract

The selectivity of the domino reaction of the (het)aryl azides, containing the carbonyl center in the ortho position to the azido group, with malonodinitrile dimer was studied. It has been shown that in the case of aromatic azides bearing a carboxy or nitrile function in the ortho position, the reaction occurred with the formation of exclusively [1,2,3]triazolo[1,5-a]pyrimidine instead of [1,2,3]triazolo[4,5-b]pyridine system. Thus, new [1,2,3]triazolo[1,5-a]quinazolines, thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine, and thieno[3,2-e][1,2,3]triazolo[1,5-a]-pyrimidines, having polyfunctional 1-amino-2,2-dicyanovinyl fragment, were prepared in short time in high yields.