Dehydrogenative N-incorporation: a direct approach to quinoxaline N-oxides under mild conditions

Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10495-9. doi: 10.1002/anie.201406479. Epub 2014 Aug 5.

Abstract

An efficient method for the synthesis of quinoxaline N-oxides proceeds by the dehydrogenative N-incorporation of simple imines by C(sp(2))-H and C(sp(3))-H bond functionalization. The overall transformation involves the cleavage of three C-H bonds. The reaction is easily handled and proceeds under mild conditions. Simple and readily available tert-butyl nitrite (TBN) was employed as the NO source.

Keywords: CN bond formation; cyclization; dehydrogenative coupling; imines; nitrogen oxides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Cyclization
  • Hydrogen / chemistry
  • Imines / chemistry
  • Nitrogen / chemistry*
  • Oxides / chemistry
  • Quantum Theory
  • Quinoxalines / chemistry*

Substances

  • Imines
  • Oxides
  • Quinoxalines
  • Carbon
  • Hydrogen
  • Nitrogen