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


Yildirim I., Kandemirli F., Demir E.

MOLECULES, vol.10, no.3-5, pp.559-571, 2005 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 10 Issue: 3-5
  • Publication Date: 2005
  • Doi Number: 10.3390/10030559
  • Title of Journal : MOLECULES
  • Page Numbers: pp.559-571
  • Keywords: furan-2,3-dione, pyrazole-3-carboxylic acid, pyrazole-3-carboxylic acid chloride, imidazo [4,5-b]pyridine, IR and NMR spectra, MO calculations, CYCLIC OXALYL COMPOUNDS, HETEROCYCLIC-COMPOUNDS, CYCLIZATION REACTIONS, BIOLOGICAL-ACTIVITY, 4-BENZOYL-2,3-DIOXO-5-PHENYL-2,3-DIHYDROFURAN, 4-BENZOYL-5-PHENYL-2,3-FURANDIONE, 1H-PYRIMIDINES, DERIVATIVES

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.