Mechanosynthesis of pharmaceutically relevant sulfonyl-(thio)ureas

Chem Commun (Camb). 2014 May 25;50(40):5248-50. doi: 10.1039/c3cc47905f. Epub 2013 Nov 20.

Abstract

We demonstrate the first application of mechanochemistry to conduct the synthesis of sulfonyl-(thio)ureas, including known anti-diabetic drugs tolbutamide, chlorpropamide and glibenclamide, in good to excellent isolated yields by either stoichiometric base-assisted or copper-catalysed coupling of sulfonamides and iso(thio)cyanates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chlorpropamide / chemical synthesis*
  • Copper / chemistry*
  • Glyburide / chemical synthesis*
  • Hypoglycemic Agents / chemical synthesis*
  • Isothiocyanates / chemistry*
  • Molecular Structure
  • Sulfonamides / chemistry*
  • Tolbutamide / chemical synthesis*

Substances

  • Hypoglycemic Agents
  • Isothiocyanates
  • Sulfonamides
  • Copper
  • Tolbutamide
  • Glyburide
  • Chlorpropamide