Abstract
Herein, we report the first examples of the Mitsunobu alkylation of β-alkoxycarbonyl 2-nitrobenzenesulfones. Wang resin was acylated with α-halocarboxylic acids followed by the reaction with 2-nitrothiophenols. After oxidation with m-chloroperbenzoic acid, the immobilized β-alkoxycarbonyl 2-nitrobenzensulfones were subjected to alkylation with various alcohols. The reaction outcome strongly depended on the selection of the alkylating species. After the reduction of the nitro group, acid-mediated cleavage and subsequent cyclization, the C2-(di)substituted benzothiazin-3(4H)-one 1,1-dioxides were obtained in high crude purities and good overall yields.
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