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Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐ c ]pyrazole‐5‐carboxamide
Author(s) -
Saber Ahmed F.,
Zaki Remon M.,
Kamal ElDean Adel M.,
Radwan Shaban M.
Publication year - 2020
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.3769
Subject(s) - chemistry , pyrazole , carboxamide , hydrazine (antidepressant) , phthalic anhydride , hydrate , carbohydrazide , antifungal , derivative (finance) , yield (engineering) , proton nmr , carbon 13 nmr , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , catalysis , medicine , materials science , chromatography , dermatology , financial economics , economics , metallurgy
The starting compound 4‐amino‐3‐methyl‐1‐phenyl‐1 H ‐thieno[2,3‐ c ]pyrazole‐5‐carboxamide (1) , that has been previously synthesized according to the literature procedure, underwent a reaction with the anhydride of phthalic acid either in AcOH or DMF to give isoindolinylpyrazole‐5‐carboxamide 3 and pyrazolothienopyrimidoisoindoledione 4 , respectively. Also, it was subjected to react with diethylmalonate followed by hydrazinolysis by hydrazine hydrate to yield the pyrazolothienopyrimidinyl acetohydrazide 5 . The carbohydrazide derivative 5 was used as a key intermediate for the preparation of other new heterocyclic systems containing pyrazolylacetyl pyrazolothienopyrimidines and pyrazolothieno‐pyrimidotriazepine compounds 6–11 . The structures of these new heterocycles have been characterized by using analytical and spectroscopic analyses (IR, 1 H‐NMR, 13 C‐NMR and MS). Some derivatives of the synthesized compounds exhibited remarkable antibacterial and antifungal activities against many bacterial and fungal strains.