Synthesis ( IF 2.2 ) Pub Date : 2019-08-01 , DOI: 10.1055/s-0037-1610724 Xu Zhang , Wen-Bin Cao , Xiao-Ping Xu 1 , Shun-Jun Ji
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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.
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.
中文翻译：
NBS在水中处理烯烃酰胺：一溴和多溴苯并恶嗪的合成
抽象的
据报道在水中用N-溴琥珀酰亚胺（NBS）处理烯烃酰胺。一溴苯并恶嗪主要在室温下形成，而在80°C时优先生成多溴苯并恶嗪。机理研究表明，该反应可能通过在C = C键处进行亲电加成，然后在芳环上进行亲电取代而进行。在该协议中不需要添加剂。
据报道在水中用N-溴琥珀酰亚胺（NBS）处理烯烃酰胺。一溴苯并恶嗪主要在室温下形成，而在80°C时优先生成多溴苯并恶嗪。机理研究表明，该反应可能通过在C = C键处进行亲电加成，然后在芳环上进行亲电取代而进行。在该协议中不需要添加剂。
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