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

被引：13

作者：

Zhang, Xu

Cao, Wen-Bin

Xu, Xiao-Ping ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 20期

基金：

中国国家自然科学基金;

关键词：

benzoxazines; water; metal free; bromination; selectivity; N-BROMOSUCCINIMIDE; ORGANIC-REACTIONS; ACCESS; POTENT; INHIBITORS; MECHANISM; INDOLES; CASCADE;

D O I：

10.1055/s-0037-1610724

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of olefinic amides with N -bromosuccinimide (NBS) in water is reported. Monobromobenzoxazines were mainly formed at room temperature, while at 80 degrees 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.

引用

页码：3805 / 3814

页数：10

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