Synthesis 2019; 51(20): 3805-3814
DOI: 10.1055/s-0037-1610724
paper
© Georg Thieme Verlag Stuttgart · New York

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
,
› Institutsangaben
We gratefully acknowledge the National Natural Science Foundation of China (21772138 and 21672157), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201708) and Soochow University.
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Publikationsverlauf

Received: 25. April 2019

Accepted after revision: 09. Juli 2019

Publikationsdatum:
01. August 2019 (online)


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.

Supporting Information

 
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