Solid-phase synthesis of pyrazolopyridines from polymer-bound alkyne and azomethine imines

J Comb Chem. May-Jun 2006;8(3):344-9. doi: 10.1021/cc050138j.

Abstract

Study was made of the 1,3-dipolar cycloaddition of polymer-bound alkynes to azomethine imines generated in situ from N-aminopyridine iodides. Aromatization of the cycloadducts gives polymer-bound pyrazolopyridines that can be released from the resin as carboxylic acids with trifluoroacetic acid or as methyl esters with sodium methoxide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azo Compounds / chemistry*
  • Imines / chemistry*
  • Methanol / chemistry
  • Models, Chemical
  • Polymers / chemistry
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Technology, Pharmaceutical

Substances

  • Alkynes
  • Azo Compounds
  • Imines
  • Polymers
  • Pyrazoles
  • Pyridines
  • azomethane
  • Methanol