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光化学两步形式[5+2]环加成反应:一种合成取代氮杂环庚烷的缩合/扩环方法

A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

作者信息

Thullen Scott M, Rubush David M, Rovis Tomislav

机构信息

Department of Chemistry, Columbia University, New York, NY 10027.

Department of Chemistry, Colorado State University, Fort Collins, CO 80523.

出版信息

Synlett. 2017 Dec;28(20):2755-2758. doi: 10.1055/s-0036-1589049. Epub 2017 Jun 29.

Abstract

Seven-membered nitrogen-containing heterocycles are considerably underrepresented in the literature compared to their five- and six-membered analogues. Herein, we report a relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two step procedure.

摘要

与五元及六元类似物相比,七元含氮杂环在文献中的报道相当少。在此,我们报道了一种研究相对较少的光化学重排反应,该反应可将N-乙烯基吡咯烷酮高产率地转化为氮杂䓬-4-酮。这种转化能够通过一个简便的两步过程,将易得的吡咯烷酮和醛转化为功能密集的氮杂环庚烷衍生物。

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