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Synthesis, Spectral Characterization, Cytotoxic, and Antimicrobial Activities of Some Novel Heterocycles Utilizing 1,3‐Diphenylpyrazole‐4‐carboxaldehyde Thiosemicarbazone
Author(s) -
Ramadan Sayed K.,
Sallam Hanan A.
Publication year - 2018
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.3232
Subject(s) - chemistry , chloroacetic acid , ethyl chloroacetate , thiazole , semicarbazone , ethyl acetoacetate , acetylacetone , chloroacetyl chloride , malononitrile , phenacyl bromide , organic chemistry , dimethyl acetylenedicarboxylate , hydrazide , malonic acid , hydrazine (antidepressant) , thionyl chloride , diazepine , ethyl bromoacetate , hydrate , chloride , ring (chemistry) , catalysis , cycloaddition , chromatography
A new series of heterocycles was synthesized via the reaction of readily obtainable 1,3‐diphenylpyrazole‐4‐carboxaldehyde thiosemicarbazone with many carbon electrophiles, for example, chloroacetic acid, chloroacetyl chloride, ethyl chloroacetate, dimethyl acetylenedicarboxylate, maleic anhydride, 3′‐nitro‐ω‐bromoacetophenone, malonic acid, acetylacetone, ethyl benzoylacetate, arylidene malononitrile, and ethyl cyanoacetate in attempt to construct imidazolidinone, thiazolidinone, thiazole, and pyrimidine derivatives. The behavior of the titled compound towards hydrazine hydrate was investigated, in addition to the ring closure under different conditions. Also, the reactions with 2‐chloroquinoline‐3‐carboxaldehyde and chromone‐3‐carboxaldehyde were discussed. The structures of all products obtained were substantiated from their analytical and spectral data. The antitumor and antimicrobial activities of the synthesized compounds were examined.