EFFECT OF ELECTRON DONATING AND ELECTRON WITHDRAWING GROUP ON THE SYNTHESIS OF 1-PHENYL-3-(4-METHOXYPHENYL)-2,3-EPOXY-1-PROPANANONE, 1-PHENYL-3-(4-CHLOROPHENYL)-2,3-EPOXY-1-PROPANANONE, AND 1-(2,4-DINITROPHENYL)-3-PHENYL-5-(4-METHOXYPHENYL)-1H-PYRAZOL-4-OL

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O.B. Ovonramwen, C.K. Okekearu, H.C. Ndibe, O.K Ogbeide

Department of Chemistry, Faculty of Physical Sciences, University of Benin, Benin city, Nigeria

Nigerian Journal of Applied Science, 41-2

Publication Date: 2024-01-16

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Abstract

In this paper, two chalcone epoxides, 1-phenyl-3-(4-methoxyphenyl)-2,3-epoxy-1-propananone and 1-phenyl-3-(4-chlorophenyl)-2,3-epoxy-1-propananone were synthesised from phenacyl bromide and 4-anisaldehyde and 4-chlorobenzaldehyde respectively. The methoxy (electron-donating) chalcone epoxide was synthesised in 35 min, compared to the 1 h, 20 min synthesis completion time of the chloro (electron-withdrawing) chalcone epoxide. The 1-(2,4-dinitrophenyl)-3-phenyl-5-(4-methoxyphenyl)-1H-pyrazol-4-ol was synthesised from 1-phenyl-3-(4-methoxyphenyl)-2,3-epoxy-1-propananone and 2,4-dinitrophenylhydrazine. The synthesised compounds were characterised using UV, FTIR, and 1HNMR. 1-phenyl-3-(4-methoxyphenyl)-2,3-epoxy-1-propananone, 1-phenyl-3-(4-chlorophenyl)-2,3-epoxy-1-propananone and 1-(2,4-dinitrophenyl)-3-phenyl-5-(4-methoxyphenyl)-1H-pyrazol-4-ol were synthesised. The successful synthetic approach through a moderated reaction method with easily sourced reagents and structural analysis afforded the compounds moderate yields and staged a potential for advancing multiple fields, including pharmaceuticals, drug development, agriculture, and the chemical industry.

Keywords: Oxirane, Chalcone, Pyrazole, Darzens Synthesis