One-step synthesis of 5,6-diaryl pyridine-2(1H)-thiones from isoflavones

Org Biomol Chem. 2013 Mar 28;11(12):2034-8. doi: 10.1039/c3ob27247h. Epub 2013 Feb 8.

Abstract

The one-step cyclocondensation of substituted isoflavones with cyanothioacetamide in the presence of sodium hydroxide gave an array of 3-cyano-5,6-diaryl pyridine-2(1H)-thiones in good yields. The procedure involves base-mediated ring opening of the isoflavones and subsequent Knoevenagel condensation between the 1,3-dicarbonyl intermediate generated from the isoflavones and cyanothioacetamide, followed by ring closure and dehydration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Isoflavones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Thiones / chemical synthesis*
  • Thiones / chemistry

Substances

  • Isoflavones
  • Pyridines
  • Thiones