Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions

Abstract

Reaction of benzimidazolone derivatives, or their thio- or aza-counterparts, with an isocyanide in the presence of acetone unexpectedly gave rise to novel tricyclic benzodiazepine derivatives in good yield by means of a four-component reaction incorporating two moles of acetone. Benzimidazole starting substrates bearing an electron-withdrawing group gave rise instead to dihydroquinoxaline derivatives by means of a three-component reaction. Use of deuterated acetone instead of acetone in the reactions significantly affected yield and reactivity in the four-component reaction but not in the three-component reaction.