ANRORC-type reactions of azolo[1,5-a]pyrimidine-6-carbonitriles with O- and N-nucleophiles†

Abstract

Azolo[1,5-a]pyrimidines represent an important class of nitrogen-containing heterocycles due to a wide range of useful properties. In this work, we have investigated in detail the ANRORC-type reactions for aryl-azolo[1,5-a]pyrimidine-6-carbonitriles and their benzannelated analogs initiated by treatment with O- and N-nucleophiles. The reactivity of the starting azolopyrimidines was studied, and the proposed mechanisms were confirmed by DFT-calculations.