Synthesis of Pyrazolo[1,5‐a][1,3,5]triazine, Pyrazolo[1,5‐a]pyrimidine, and Imidazo[1,2‐b]pyrazole Derivatives Based on Imidazo[2,1‐b]thiazole Moiety

3(5)‐Aminopyrazole derivative (6) has been synthesized by the reactions of the versatile unreported 2‐cyano‐N′‐(1‐(3‐methyl‐6‐phenylimidazo[2,1‐b]thiazol‐2‐yl)ethylidene)acetohydrazide (3) with phenyl isothiocyanate in KOH/DMF solution followed by reaction with methyl iodide and hydrazine hydrate. R...

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Veröffentlicht in:Journal of heterocyclic chemistry 2017-07, Vol.54 (4), p.2405-2416
Hauptverfasser: Dawood, Kamal M., Sayed, Samia M., Raslan, Mohamed A.
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Sprache:eng
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Zusammenfassung:3(5)‐Aminopyrazole derivative (6) has been synthesized by the reactions of the versatile unreported 2‐cyano‐N′‐(1‐(3‐methyl‐6‐phenylimidazo[2,1‐b]thiazol‐2‐yl)ethylidene)acetohydrazide (3) with phenyl isothiocyanate in KOH/DMF solution followed by reaction with methyl iodide and hydrazine hydrate. Reaction of compound 6 with some 1,3‐dicarbonyl compounds yielded pyrazolo[1,5‐a]pyrimidine derivatives (14–17). Alkylation of compound 6 with various halo reagents, followed by intramolecular cyclization, yielded the corresponding imidazo[1,2‐b]pyrazole derivatives 27, 29, 31, and 33. All newly synthesized compounds were elucidated by considering the data of both elemental analysis and spectral data.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2836