Treatment of Olefinic Amides with NBS in Water: Synthesis of Monobromo- and Multibromobenzoxazines

Xu Zhang; Wen-Bin Cao; Xiao-Ping Xu; Shun-Jun Ji

doi:10.1055/s-0037-1610724

Synthesis, Table of Contents

Synthesis 2019; 51(20): 3805-3814
DOI: 10.1055/s-0037-1610724

paper

Treatment of Olefinic Amides with NBS in Water: Synthesis of Monobromo- and Multibromobenzoxazines

Xu Zhang

,

Wen-Bin Cao

,

Xiao-Ping Xu∗

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China Email: xuxp@suda.edu.cn Email: shunjun@suda.edu.cn

,

Shun-Jun Ji ∗

› Author Affiliations

Abstract

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Abstract

Treatment of olefinic amides with N-bromosuccinimide (NBS) in water is reported. Monobromobenzoxazines were mainly formed at room temperature, while at 80 °C multibromobenzoxazines were preferentially generated. Mechanism studies showed that the reaction might proceed via a cascade of electrophilic addition at the C=C bond followed by electrophilic substitution at the aromatic ring. No additives are required in this protocol.

Key words

benzoxazines - water - metal free - bromination - selectivity

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References

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Supplementary Material

Supporting Information