Aza-Michael Mono-addition Using Acidic Alumina under Solventless Conditions

Molecules. 2016 Jun 22;21(6):815. doi: 10.3390/molecules21060815.

Abstract

Aza-Michael reactions between primary aliphatic and aromatic amines and various Michael acceptors have been performed under environmentally-friendly solventless conditions using acidic alumina as a heterogeneous catalyst to selectively obtain the corresponding mono-adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylonitrile, methyl acrylate and acrylamide were also utilized successfully. Bi-functional amines also gave the mono-adducts in good to excellent yields. Such compounds can serve as intermediates for the synthesis of anti-cancer and antibiotic drugs.

Keywords: Aza-Michael reactions; acidic alumina; mono-addition; primary amines; solvent-free.

MeSH terms

  • Acids / chemistry
  • Acrylamide / chemistry
  • Acrylates / chemistry
  • Acrylonitrile / chemistry
  • Aluminum Oxide / chemistry*
  • Aluminum Oxide / therapeutic use
  • Amines / chemistry*
  • Amines / therapeutic use
  • Catalysis*
  • Humans
  • Inflammation / drug therapy
  • Neoplasms / drug therapy
  • Solvents

Substances

  • Acids
  • Acrylates
  • Amines
  • Solvents
  • Acrylamide
  • Aluminum Oxide
  • Acrylonitrile
  • methyl acrylate