Vinyl azide strategy for the synthesis of tetrasubstituted pyrimidines

Abstract

In our research group, a new preparative procedure for the synthesis of tetrasubstituted pyrimidine derivatives from α-azidocinnamates was developed. The synthesis consists of the following stages: (i) LED light induced dimerization of α-azidocinnamates to 1,3-diazabicyclo[3.1.0]hex-3-enes via formation of 2H-azirines, (ii) DBU-catalyzed isomerization of 1,3-diazabicyclo[3.1.0]hex-3-enes to 1,6-dihydropyrimidines, (iii) aromatization of 1,6-dihydropyrimidines using DDQ.