The starting 3-(3,5-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile (1) reacts with phenyl isothiocyanate and ethyl bromoacetate to give the corresponding thiazole derivative 4. On repetition of the reaction using phenacyl bromides 5a–d (instead of ethyl bromoacetate), oxathiepine-6-carbonitriles 10a–d were obtained. Coupling of compound 1 with aryldiazonium chlorides gives the corresponding 2-(arylhydrazono)-(3,5-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile derivatives 12a–e, which on treatment with p-phenylenediamine, followed by reaction of hydrazine hydrate afforded pyrazole derivatives 15a–d. The reaction of 1 with 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile afforded the respective 2-cyanomethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivative 18. Compound 18 reacted with phenyl isothiocyanate in the presence of potassium hydroxide at room temperature and then phenacyl bromide was added; the pyrazolopyrimidines 24 were obtained. The structures of all the newly synthesized products were confirmed based on elemental, spectral data and a plausible mechanism has been postulated to account for their formation. Also, we evaluate the anticancer activity of some representative examples of the newly synthesized compounds.
Research on Chemical Intermediates – Springer Journals
Published: May 5, 2015
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