Facile Synthesis and Antimicrobial Activity of 5‐Amino‐3‐methyl‐1‐phenyl‐1 H ‐thieno[3,2‐ c ]pyrazole‐6‐carbonitrile and Their Derivatives

5‐Amino‐thieno[3,2‐ c ]pyrazole derivative 2 was prepared by Gewald reaction in a one‐pot procedure. The amino group of compound 2 like primary aromatic amine formed the diazonium salt when treated with NaNO 2 /HCl, followed by coupling with different nucleophiles to yield the azo coupling products...

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Veröffentlicht in:Journal of heterocyclic chemistry 2019-01, Vol.56 (1), p.226-233
Hauptverfasser: Regal, Mohsen K. A., Shaban, Safa S., El‐Metwally, Souad A.
Format: Artikel
Sprache:eng
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Zusammenfassung:5‐Amino‐thieno[3,2‐ c ]pyrazole derivative 2 was prepared by Gewald reaction in a one‐pot procedure. The amino group of compound 2 like primary aromatic amine formed the diazonium salt when treated with NaNO 2 /HCl, followed by coupling with different nucleophiles to yield the azo coupling products 3a – d . The reactivity of 5‐amino‐thienopyrazole 2 has been investigated towards different electrophilic reagents such as aromatic aldehydes, alkyl halide, acid chloride, acid anhydride, phenyl isothiocyanate, carbon disulfide, ethyl glycinate, and thioacetamide, which afforded the reaction products 4 – 14 , respectively.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3399