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)

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

Published: July 2013

AI Article Synopsis

  • 2,6-Diazasemibullvalenes (NSBVs) react with oxygen under mild conditions, resulting in the formation of Δ(1)-bipyrrolinones through C-N bond cleavage and C-H bond oxidation.
  • NSBVs can also generate pyrrolino[3,2-b]pyrrolinone derivatives when combined with N-oxides and Lewis acids.
  • The Δ(1)-bipyrrolinones produced can be easily converted into various other heterocyclic compounds.

Article 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.

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http://dx.doi.org/10.1039/c3cc43061hDOI Listing

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