A new mild base-catalyzed Mannich reaction of hetero-arylamines in water: highly efficient stereoselective synthesis of beta-aminoketones under microwave heating

Org Biomol Chem. 2009 Apr 7;7(7):1410-4. doi: 10.1039/b819763f. Epub 2009 Feb 24.

Abstract

A new mild base-catalyzed Mannich reaction of aromatic aldehydes with 1,2-diphenylethanone and hetero-arylamines including pyridin-2-amine and pyrimidin-2-amine is described. In this reaction, a series of new beta-aminoketones were stereoselectively synthesized in water by controlling the steric hindrance of the substrates under microwave heating. This method has the advantages of a short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environmental impact.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Amines / chemistry*
  • Benzoin / analogs & derivatives
  • Benzoin / chemistry
  • Catalysis
  • Heating*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Mannich Bases / chemistry*
  • Microwaves*
  • Molecular Structure
  • Stereoisomerism
  • Water / chemistry

Substances

  • Aldehydes
  • Amines
  • Ketones
  • Mannich Bases
  • Water
  • deoxybenzoin
  • Benzoin