Oxidation of C–H bonds to CO bonds by O2 only or N-oxides and DMSO: synthesis of Δ1-bipyrrolinones and pyrrolino[3,2-b]pyrrolinones from 2,6-diazasemibullvalenes

Abstract

2,6-Diazasemibullvalenes (NSBVs) readily reacted with oxygen under mild conditions, affording Δ¹-bipyrrolinones via C–N bond cleavage and C–H bond oxidation. Pyrrolino[3,2-b]pyrrolinone derivatives were efficiently generated when NSBVs were treated with N-oxides in the presence of Lewis acids. Δ¹-Bipyrrolinones thus obtained could be readily transformed into other heterocycles.