Solid-phase synthesis of 5-substituted amino pyrazoles

J Comb Chem. 2005 Jul-Aug;7(4):584-8. doi: 10.1021/cc049814s.

Abstract

An efficient method for the solid-supported synthesis of 5-N-alkylamino and 5-N-arylamino pyrazoles is described. This method is general and mild and utilizes readily accessible resin-immobilized beta-ketoamides 2 as starting materials for the preparation of 1. Resin-immobilized beta-ketoamide, aryl-, or alkylhydazine and Lawesson's reagent are suspended in a mixture of THF/Py and heated at 50-55 degrees C to give a resin-bound 5-aminopyrazole, that is liberated from the solid support by treatment with TFA.

MeSH terms

  • Amines / chemistry*
  • Combinatorial Chemistry Techniques*
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry*

Substances

  • Amines
  • Pyrazoles