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

Yildirim I., Kandemirli F.

STRUCTURAL CHEMISTRY, vol.17, no.2, pp.241-247, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 2
  • Publication Date: 2006
  • Doi Number: 10.1007/s11224-006-9052-y
  • Journal Name: STRUCTURAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.241-247
  • Kocaeli University Affiliated: No

Abstract

The 1H-pyrazole-3-carboxylic acid 1 was converted via reactions of its acid chloride 2 with various aminophenol derivatives 3a-d into the corresponding N-(hydroxyphenyl)-1H-pyrazole-3-carboxamides 4a-d, respectively, in good yields (34-53%). The reactions of 1 or 2 with 3 in benzene or toluene for 5-7 h with no catalytic amounts of base lead to the formation of the products 4. The structures of all new synthesized compounds were established by the C-13 NMR, H-1 NMR, IR, masss spectroscopic data and elemental analyses. The reaction mechanism of 2 with 3 was studied by means of the RHF/3-21G and RHF/6-31G method.