Reactions of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid chloride with various hydroxylamines and carbazates

Korkusuz E., YILDIRIM İ.

TURKISH JOURNAL OF CHEMISTRY, vol.34, no.6, pp.859-867, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 6
  • Publication Date: 2010
  • Doi Number: 10.3906/kim-1004-523
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.859-867
  • Keywords: Pyrazole-3-carboxylic acid, nucleophilic substitution, furan-2,3-dione, carbazate, hydroxylamine, CYCLIC OXALYL COMPOUNDS, FUNCTIONALIZATION REACTIONS, CYCLIZATION REACTIONS, DERIVATIVES, MECHANISM
  • Kayseri University Affiliated: No

Abstract

The 1H-pyrazole-3-carboxylic acid 2 was converted via reactions of its acid chloride 3 with various hydroxylamine 4a-f and carbazate derivatives 8a-c into the corresponding novel N-substituted-4-benzoyl-1,5-dipenyl-1H-pyrazole-3-carboxamides 5a-c, N,N-disubstituted-4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylates 6d, e,4-benzoyl-N-{[(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-yl)carbonyl]oxy}-N-methyl-1,5diphenyl-1H-pyrazole-3-carboxamide (7), and 4-benzoyl-N'-(alkoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carbohydrazides 9a,b and 10, respectively, in good yields (65%-90%). The reactions of 3 with 4 and 8 in xylene for 8-15 h with catalytic amounts of base led to the formation of the products 5-7, 9, and 10. The structures of all new synthesized compounds were established by the C-13-NMR, H-1-NMR, IR spectroscopic data, and elemental analyses.