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| - A Three-Component Coupling Process Based on VicariousNucleophilic Substitution (VNSAR)−Alkylation Reactions: AnApproach to Indoprofen and Derivatives
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| - The intermediate anion derived from the vicarious nucleophilic substitution (VNS) of hydrogenreacts with a series of alkyl halides to generate the corresponding α-alkylated conventional VNSproduct in a one-pot process. This one-pot VNS−alkylation reaction offers a convenient route to arange α-substituted nitrobenzyl phosphine oxides, sulfones, and esters via a three-componentcoupling reaction. Reactions of α-chloroethyl phenyl sulfone (14) and ethyl 2-chloropropionate (16)with nitrobenzene followed by subsequent addition of an alkylating agent give a series of sulfonesand esters bearing an α-aryl quaternary center. The VNS−alkylation protocol has been applied tothe synthesis of derivatives of Indoprofen from nitrobenzene using readily available inexpensivestarting materials. Indoprofen itself was prepared using the conventional VNS reaction in foursteps and 24% overall yield from nitrobenzene.
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