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Utility of 4‐Benzylidene‐2‐phenyl‐5(4H)‐oxazolone in Synthesis of Triazine, Oxadiazole and Imidazole Derivatives of Anticipated Biological Activity
Author(s) -
Youssef Ahmed S. A.,
ElMariah Fatma A.,
AbdElmottaleb Fatma T.,
Hashem Heba E.
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2178
Subject(s) - chemistry , hydrazide , synthon , oxazolone , hydrazine (antidepressant) , hydrate , yield (engineering) , oxadiazole , semicarbazide , imidazole , derivative (finance) , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , materials science , chromatography , economics , financial economics , metallurgy
Treatment of oxazolone 1 with hydrazine hydrate at room temperature gave the (Z)‐configurated isomer hydrazide (Z)‐ 3 (high yield). However, refluxing 1 with hydrazine hydrate yielded the (E)‐configurated isomer hydrazide (E)‐ 2 (low yield).The hydrazide derivative (Z)‐ 3 has been utilized as synthon for the synthesis of 1,2,4‐triazinone, imidazolone, and oxadiazole derivatives through appropriate routes. The thiosemicarbazide and semicarbazide derivatives are synthesized by different routes. The structures of the new compounds were established on the basis of IR, 1 H‐NMR, mass spectral data, and elemental analysis.