Hydrogen bond-assisted 6π-azaelectrocyclization of penta-2,4-dienamides: synthesis of dihydropyridin-2(3H)-ones

J Org Chem. 2013 Apr 5;78(7):3323-8. doi: 10.1021/jo4001959. Epub 2013 Mar 7.

Abstract

A facile and efficient synthesis of substituted dihydropyridin-2(3H)-ones is developed from penta-2,4-dienamides, in which an intramolecular C-N bond was formed through thermal 6π-azaelectrocyclization. The intramolecular hydrogen bonding-assisted cyclization reaction opens access to a variety of dihydropyridin-2(3H)-ones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amides / chemistry*
  • Aza Compounds / chemistry*
  • Cyclization
  • Dihydropyridines / chemistry*
  • Electrons
  • Hydrogen Bonding
  • Molecular Structure

Substances

  • Alkenes
  • Amides
  • Aza Compounds
  • Dihydropyridines