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
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
Affiliation:
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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Cite this article as:
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
DOI https://dx.doi.org/10.2174/157017810791130568 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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