4.4 Article

Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides

Journal

CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 42, Issue 2, Pages 507-518

Publisher

SCIENCE PRESS
DOI: 10.6023/cjoc202108016

Keywords

tin powder; allyl bromides; benzol[e][1,2,3]oxathiazine-2,2-dioxides; allylation

Funding

  1. National Natural Science Foundation of China [21861033, 22061037]

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The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was investigated. The reaction proceeded smoothly with high yields for various substrates. The resulting allylated products underwent N-allylation reaction and then ring closing metathesis reaction, leading to the formation of diallylated products and cyclic derivatives of benzol[e][1,2,3]oxathiazine-2,2-dioxides, respectively.
The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was explored. The results showed that the allylation proceeded smoothly with high yields for a variety of substrates. When various allyl bromides were used to perform the reaction, the gamma-addition products were obtained. These allylated products underwent N-allylation reaction in the presence of base, and the diallylated products of benzol[e][1,2,3]oxathiazine-2,2-dioxides were obtained in high yields. The diallylated products of benzol[e][1,2,3] oxathiazine-2,2-dioxides further underwent ring closing metathesis reaction, and the cyclic derivatives of benzol[e][ 1,2,3] oxathiazine-2,2-dioxides were obtained in good yield.

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