邻醌甲亚胺与亚胺醚的逆电子需求偶氮-狄尔斯-阿尔德反应：苯并稠合 1,3-恶嗪的合成。
An Inverse Electron Demand Azo-Diels-Alder Reaction of o-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines.
机构信息
Department of Organic Chemistry, Chemical Technological Faculty , Samara State Technical University , 244 Molodogvardeyskaya Street , Samara 443100 , Russian Federation.
出版信息
J Org Chem. 2018 Apr 20;83(8):4775-4785. doi: 10.1021/acs.joc.8b00692. Epub 2018 Apr 6.
PMID:29595976
Abstract
We have studied the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels-Alder reaction, and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.
摘要
我们研究了邻醌甲醚前体与亚胺醚的反应。该反应为取代 1,3-苯并恶嗪的提供了一种通用途径。所提出的反应机制涉及到邻醌甲醚中间体的生成、亚胺-狄尔斯-阿尔德反应和消除。这种级联过程是亚胺醚作为亲二烯体参与的罕见实例。
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