Microwave enabled umpulong mechanism based rapid and efficient four- and six-component domino formations of 2-(2'-azaaryl)imidazoles and anti-1,2-diarylethylbenzamides

J Org Chem. 2009 Dec 18;74(24):9486-9. doi: 10.1021/jo902204s.

Abstract

Concise and efficient six-component and four-component domino approaches to anti-1,2-diarylethylbenzamides and highly substituted 2-(2'-azaaryl)imidazoles have been developed under solvent-free and microwave-irradiation conditions. The reactions showed a broad scope of substrates in which a wide range of common commercial aromatic aldehydes and heteroaryl nitriles can be used. The syntheses were finished within short periods (15-34 min) with good to excellent chemical yields and stereoselectivity that avoided tedious workup isolations. New mechanisms involving an umpolung have been proposed for these two reaction processes.

Publication types

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

MeSH terms

  • Acetates / chemistry
  • Acetates / radiation effects
  • Aldehydes / chemistry
  • Aldehydes / radiation effects
  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Ethane / analogs & derivatives
  • Ethane / chemical synthesis*
  • Ethane / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Hydrocarbons, Cyclic / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Microwaves*
  • Nitriles / chemistry
  • Nitriles / radiation effects
  • Stereoisomerism
  • Time Factors

Substances

  • Acetates
  • Aldehydes
  • Benzamides
  • Heterocyclic Compounds, 4 or More Rings
  • Hydrocarbons, Cyclic
  • Imidazoles
  • Nitriles
  • Ethane
  • ammonium acetate