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Synthesis 2019; 51(20): 3805-3814
DOI: 10.1055/s-0037-1610724
DOI: 10.1055/s-0037-1610724
paper
Treatment of Olefinic Amides with NBS in Water: Synthesis of Monobromo- and Multibromobenzoxazines
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.Further Information
Publication History
Received: 25 April 2019
Accepted after revision: 09 July 2019
Publication Date:
01 August 2019 (online)
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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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610724.
- Supporting Information
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Recent examples, see:
Recent examples, see: