Synthesis of tetrahydropyrimidin-2-ones via FeCl3 catalyzed one-pot domino reaction of amines, methyl propiolate, aromatic aldehydes, and urea

Mol Divers. 2014 Feb;18(1):79-89. doi: 10.1007/s11030-013-9487-1. Epub 2013 Oct 25.

Abstract

Polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives could be selectively produced from the one-pot domino reaction of arylamines, methyl propiolate, aromatic aldehydes, and urea in ethanol in the presence of FeCl3 as catalyst. Under similar reactions secondary amines such as morpholine and piperidine predominately afford tetrahydropyrimidin-2-one derivatives in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkynes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Chlorides / chemistry*
  • Ferric Compounds / chemistry*
  • Propionates / chemistry*
  • Pyrimidinones / chemical synthesis*
  • Pyrimidinones / chemistry*
  • Urea / chemistry*

Substances

  • Aldehydes
  • Alkynes
  • Amines
  • Chlorides
  • Ferric Compounds
  • Propionates
  • Pyrimidinones
  • tetrahydropyrimidinone
  • Urea
  • ferric chloride