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, cilt.34, sa.6, ss.859-867, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 34 Sayı: 6
  • Basım Tarihi: 2010
  • Doi Numarası: 10.3906/kim-1004-523
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.859-867
  • Anahtar Kelimeler: Pyrazole-3-carboxylic acid, nucleophilic substitution, furan-2,3-dione, carbazate, hydroxylamine, CYCLIC OXALYL COMPOUNDS, FUNCTIONALIZATION REACTIONS, CYCLIZATION REACTIONS, DERIVATIVES, MECHANISM
  • Kayseri Üniversitesi Adresli: Hayır

Özet

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.