One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions

A new synthetic method for diastereoselective synthesis of tetrahydro-pyrrolo[1,2-d][1,4]benzodiazepines and tetrahydro-pyrrolo[1,2-d][1,4]diazepinones is developed which involves 1,3-dipolar cycloaddition, N-alkylation or N-acylation and Staudinger/aza-Wittig reactions. This one-pot and three-step synthesis of four components gave two different heterocyclic scaffolds. Green chemistry metrics analysis of the reaction process provided favorable results.