On the reaction of fused benzodiazepines with alkynes containing electron-withdrawing groups

Fused benzodiazepines were found to react with activated alkynes to effect either vinylation of unsubstituted nitrogen atom or dealkylation of nitrogen and its further vinylation. For benzodiazepinones bearing lactam fragment, the reactions with alkynes proceed by several pathways: formation of vinyl-substituted benzodiazepines, the Stevens rearangement products, and expansion of the diazepine ring: benzodiazonine and diazecine. © 2012 Springer Science+Business Media New York.