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  • Title: Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals.
    Author: Savant MM, Pansuriya AM, Bhuva CV, Kapuriya N, Patel AS, Audichya VB, Pipaliya PV, Naliapara YT.
    Journal: J Comb Chem; 2010; 12(1):176-80. PubMed ID: 19950975.
    Abstract:
    A small molecule library of alkyl, sulfone, and carboxamide functionalized pyrazoles and isoxazoles has been developed via a rapid sequential condensation of various alpha-acylketene dithioacetals (1a-o) with hydrazine hydrate or hydroxylamine hydrochloride, followed by oxidation of sulfide to sulfone using water as the reaction medium. An efficient and safe oxidation of sulfides (4/5a-o) to the corresponding sulfones (6/7a-o) using sodium per borate system in aqueous medium is reported. The concise and two step synthesis of trisubstituted pyrazoles and isoxazoles was investigated under variety of reaction condition. The newly developed methodology has the advantage of excellent yield and chemical purity with short reaction time using water as a solvent.
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