K2CO3-mediated synthesis of functionalised 4-substituted-2-amino-3-cyano-4H-chromenes via Michael-cyclization reactions

Molecules. 2014 Nov 25;19(12):19253-68. doi: 10.3390/molecules191219253.

Abstract

An efficient approach for the synthesis of functionalized 4-substituted-2-amino-3-cyano-4H-chromenes moderate to high yields (up to 98%) has been achieved via a tandem K2CO3 catalyzed conjugate addition-cyclization reaction of malononitrile and a range of Knoevenagel adducts previously formed from oxindole, pyrazolone, nitromethane, N,N-dimethylbarbituric acid or indanedione. This methodology differs from the previous classical methods in its simplicity and ready availability of the catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Carbonates / chemistry*
  • Cyclization
  • Potassium / chemistry*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Benzopyrans
  • Carbonates
  • potassium carbonate
  • Potassium