Synthesis of aminoquinolones from triazoles via carboxamidoketenimine and amidinoketene intermediates

Abstract

1-Aryl-1H-1,2,3-triazole-4-carboxamides 7d–f have been synthesized and converted to 2-dimethylamino-4-quinolones 12d–f by flash vacuum thermolysis (FVT). The reaction takes place via carboxamidoketenimine 9 and amidinoketene intermediates 10. The former are observed by FTIR spectroscopy at 77 K or in Ar matrices at 12 K.