Additive-free nucleophilic addition of imidazolines and imidazoles to haloacetylenes

Org Lett. 2012 Jan 6;14(1):34-7. doi: 10.1021/ol2027448. Epub 2011 Nov 29.

Abstract

Nucleophilic addition of imidazolines to 1-halo-1-alkynes takes place by simple heating in DMF without any additives to give (Z)-N-(1-halo-1-alken-2-yl)imidazolines in good yield and in a highly regio- and stereoselective manner. These reaction conditions are also valid for the similar addition of imidazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / chemistry*
  • Bromine / chemistry*
  • Chlorine / chemistry*
  • Imidazoles / chemistry*
  • Imidazolines / chemistry*
  • Iodine / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Imidazoles
  • Imidazolines
  • Chlorine
  • Iodine
  • Acetylene
  • Bromine