Experimental and theoretical studies on the functionalization reactions of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid and acid chloride with 2,3-diaminopyridine

Molecules. 2005 Mar 31;10(3):559-71. doi: 10.3390/10030559.

Abstract

The 1H-pyrazole-3-carboxylic acid 2 was converted in good yield (69%) into the corresponding 1H-pyrazole-3-carboxamide 5 via reaction of the acid chloride 3 with 2,3- diaminopyridine (4). A different product, the 3H-imidazo[4,5-b] pyridine derivative 6, was formed from the reaction of 3 with 4 and base in benzene for 5 hours. The structures of the synthesized compounds were determined spectroscopically. The mechanism of the reaction between 3 and 4 was examined theoretically.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids, Heterocyclic / chemical synthesis
  • Acids, Heterocyclic / chemistry
  • Aminopyridines / chemistry*
  • Benzoates / chemistry
  • Carboxylic Acids / chemistry*
  • Chemistry, Pharmaceutical
  • Chlorides / chemistry*
  • Kinetics
  • Models, Molecular
  • Molecular Conformation
  • Pyrazoles / chemistry*
  • Thermodynamics

Substances

  • Acids, Heterocyclic
  • Aminopyridines
  • Benzoates
  • Carboxylic Acids
  • Chlorides
  • Pyrazoles
  • 2,3-diaminopyridine