Preparation of 5,5-Bis(ethoxycarbonyl)-5,6-dihydro-3,7-diaryl-4<i>H</i>-1,2-diazepines and Their Halogenations

Abstract

Abstract 5,5-Bis(ethoxycarbonyl)-5,6-dihydro-3,7-diaryl-4H-1,2-diazepines (4) were prepared by the condensation of α-bromoacetophenone azines with diethyl malonate in the presence of sodium ethoxide. Halogenation of 4 afforded 7,7-bis(ethoxycarbonyl)-2,5-diaryl-3,4-diazanorcaradiene, 4,6-dihalodihydrodiazepines, 1-halodiazanorcaradienes, and/or 4,4,6,6-tetrachlorodihydrodiazepine, whose relative yields depended upon the reaction conditions. Dehalogenation of the halogenated products was also investigated.