导向不寻常化学的反应中间体：戴维斯-贝鲁特反应中意想不到的邻氨基苯甲酸产物。
Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.
机构信息
Department of Chemistry, University of California, Davis , 1 Shields Ave., Davis, California 95616, United States.
Department of Chemistry, American University of Beirut , Beirut 1107 2020, Lebanon.
出版信息
J Org Chem. 2017 Oct 20;82(20):10875-10882. doi: 10.1021/acs.joc.7b01521. Epub 2017 Sep 28.
Abstract
The discovery of a new variation on the Davis-Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity-a potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described.
摘要
描述了戴维斯-贝鲁特反应的一种新变体的发现，其中一个非典型的杂环骨架（邻氨基苯甲酸或苯并[c]异恶唑骨架）是由于关键反应中间体偏离其预期反应性而形成的——这是一种潜在的通用反应设计和开发方法。描述了所提出的机制和反应性改变的起源的实验和计算支持。
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