Novel Synthesis of 3-Arylated 5,6-Dimethoxybenzo[d]isothiazole 1,1- Dioxides

Fei      Xie; Bing-Lei      Gao; De-Feng      Wang; Zhao-Peng      Liu

doi:10.2174/157017810791130568

Abstract

A novel simple three-step synthesis of 3-arylated 5,6-dimethoxybenzo[d]isothiazole 1,1-dioxide is reported. ortho-Lithiation of N-tert-butyl-3,4-dimethoxybenzenesulfonamide followed by reaction with aryl aldehydes gave carbinol sulfonamides, which were oxidized into ketosulfonamides and converted to the ketimines via TMSCl/NaI/MeCN reagent mediated novel cyclization.

Keywords: Ketimines, TMSCl/NaI/MeCN, cyclization, benzo[d]isothiazoles, sulfonamides

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Letters in Organic Chemistry

Title: Novel Synthesis of 3-Arylated 5,6-Dimethoxybenzo[d]isothiazole 1,1- Dioxides

Volume: 7 Issue: 4

Author(s): Fei Xie, Bing-Lei Gao, De-Feng Wang and Zhao-Peng Liu

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Keywords: Ketimines, TMSCl/NaI/MeCN, cyclization, benzo[d]isothiazoles, sulfonamides

Abstract: A novel simple three-step synthesis of 3-arylated 5,6-dimethoxybenzo[d]isothiazole 1,1-dioxide is reported. ortho-Lithiation of N-tert-butyl-3,4-dimethoxybenzenesulfonamide followed by reaction with aryl aldehydes gave carbinol sulfonamides, which were oxidized into ketosulfonamides and converted to the ketimines via TMSCl/NaI/MeCN reagent mediated novel cyclization.

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Xie Fei, Gao Bing-Lei, Wang De-Feng and Liu Zhao-Peng, Novel Synthesis of 3-Arylated 5,6-Dimethoxybenzo[d]isothiazole 1,1- Dioxides, Letters in Organic Chemistry 2010; 7 (4) . https://dx.doi.org/10.2174/157017810791130568