Open AccessSynthesis of 1-(2,4-Dinitrophenyl)-3,5-diphenyl-1H-pyrazol-4-ol via trans-1,3-Diphenyl-2,3-epoxy-1-propanone
Author(s) -
Oluwaseyi Bukky Ovonramwen
Publication year - 2021
Publication title -
tanzania journal of science/tanzania journal of science
Language(s) - English
Resource type - Journals
eISSN - 2507-7961
pISSN - 0856-1761
DOI - 10.4314/tjs.v47i3.32
Subject(s) - dinitrophenyl , chemistry , phenylhydrazine , epoxy , dihedral angle , ring (chemistry) , medicinal chemistry , organic chemistry , hydrogen bond , molecule , antibody , immunology , biology
The trans-1,3-diphenyl-2,3-epoxy-1-propanone was synthesized from benzaldehyde and 2-bromoacetophenone in 20 min which is more economical. The presence of ethanol and Br in 2-bromoacetophenone facilitated the reaction. The vicinal diaxial coupling constant of trans-1,3-diphenyl-2,3-epoxy-1-propanone was zero, an indication of trans configuration for a rigid 3-membered ring at ~90o dihedral angle. 1-(2,4-Dinitrophenyl)-3,5-diphenyl-1H-pyrazol-4-ol was synthesized from trans-1,3-diphenyl-2,3-epoxy-1-propanone and 2,4-dinitro phenylhydrazine in glacial CH3COOH to give 85.5% yield and characterized using FTIR, 1H, 13C NMR, DEPT 135 and MS spectra. The 1-(2,4-dinitrophenyl)-3,5-diphenyl-1H-pyrazol-4-ol can be exploited for unique biological activities and in the synthesis of synthetic fibers.
Keywords: 1-(2,4-dinitrophenyl)-3,5-diphenyl-1H-pyrazol-4-ol, trans-1,3-diphenyl-2,3-epoxy-1-propanone; synthesis; 2,4-dinitro phenylhydrazine