Aza-Nazarov reaction and the role of superelectrophiles

Org Lett. 2007 Aug 2;9(16):3085-8. doi: 10.1021/ol0711570. Epub 2007 Jul 14.

Abstract

The superacid-catalyzed reactions of N-acyliminium ion salts have been studied. The new conversions are remarkably similar to the Nazarov reaction and dicationic superelectrophilic species are thought to be involved. Experimental studies show that the cyclizations may be used to prepare varied heterocyclic products, while theoretical studies show that formation of the superelectrophiles can lead to very favorable reaction energetics.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Electrochemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Imines / chemistry
  • Molecular Structure

Substances

  • Aza Compounds
  • Heterocyclic Compounds
  • Imines