Stable hemiaminals containing a triazole ring

Abstract

Reactions between 4-amino-1,2,4-triazole and nitro-substituted benzaldehydes in acetonitrile under neutral conditions afford stable hemiaminals, seven of which have been structurally and spectroscopically characterized. Two Schiff bases have also been obtained after the addition of hydrochloric acid to the reaction mixture. We describe a correlation between the conformation and configuration of the hemiaminals, and conclude that the formation of these species is determined by the substituents on the phenyl ring, as well as by the presence of 4-amino-1,2,4-triazole.