Oxidation of C-H bonds to C=O bonds by O2 only or N-oxides and DMSO: synthesis of Δ(1)-bipyrrolinones and pyrrolino[3,2-b]pyrrolinones from 2,6-diazasemibullvalenes

Shaoguang Zhang; Ming Zhan; Qian Luo; Wen-Xiong Zhang; Zhenfeng Xi

doi:10.1039/c3cc43061h

Oxidation of C-H bonds to C=O bonds by O2 only or N-oxides and DMSO: synthesis of Δ(1)-bipyrrolinones and pyrrolino[3,2-b]pyrrolinones from 2,6-diazasemibullvalenes

Chem Commun (Camb). 2013 Jul 14;49(55):6146-8. doi: 10.1039/c3cc43061h.

Authors

Shaoguang Zhang¹, Ming Zhan, Qian Luo, Wen-Xiong Zhang, Zhenfeng Xi

Affiliation

¹ Beijing National Laboratory for Molecular Sciences, MOE Key Laboratory of Bioorganic Chemistry and Molecular Engineering, College of Chemistry, Peking University, Beijing 100871, China.

PMID: 23728439
DOI: 10.1039/c3cc43061h

Abstract

2,6-Diazasemibullvalenes (NSBVs) readily reacted with oxygen under mild conditions, affording Δ(1)-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. Δ(1)-Bipyrrolinones thus obtained could be readily transformed into other heterocycles.