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通过连续的[3,3]-重排/环化反应,由N-苯氧基酰胺和炔基苯并碘恶唑酮无金属直接构建2-(恶唑-5-基)苯酚

Metal-Free Direct Construction of 2-(Oxazol-5-yl)phenols from N-Phenoxyamides and Alkynylbenziodoxolones via Sequential [3,3]-Rearrangement/Cyclization.

作者信息

Li Ming, Wang Jia-Hui, Li Wei, Wen Li-Rong

机构信息

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering , Qingdao University of Science & Technology , Qingdao , 266042 , China.

出版信息

Org Lett. 2018 Dec 7;20(23):7694-7698. doi: 10.1021/acs.orglett.8b03427. Epub 2018 Nov 29.

Abstract

A mild and straightforward synthetic protocol for the construction of 2-(oxazol-5-yl)phenol derivatives promoted by KCO from N-phenoxyamides and alkynylbenziodoxolones at room temperature has been developed. Importantly, this protocol involves a tandem sequence that includes [3,3]-rearrangement/alkylidene carbene insertion/Michael addition/cyclization. The metal-free conditions, broad substrate scope, and simple execution make this novel protocol very attractive.

摘要

已开发出一种温和且直接的合成方案,用于在室温下由碳酸钾促进从N-苯氧基酰胺和炔基苯并碘恶唑酮构建2-(恶唑-5-基)苯酚衍生物。重要的是,该方案涉及一个串联序列,包括[3,3]-重排/亚烷基卡宾插入/迈克尔加成/环化。无金属条件、广泛的底物范围和简单的操作使这个新方案非常有吸引力。

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