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可见光促进的氰基烷基化/环化级联反应在连续流中组装多杂环化合物。

Visible-Light-Promoted Cyanoalkylation/Cyclization Cascade Reaction to Assemble Polyheterocycles in Continuous Flow.

机构信息

State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, P. R. China.

出版信息

J Org Chem. 2023 Feb 17;88(4):2057-2068. doi: 10.1021/acs.joc.2c02336. Epub 2023 Jan 29.

Abstract

This study describes a visible-light-induced cascade reaction for preparing cyanoalkyl-containing polyheterocycles initiated by the photoinduced radical cascade addition of -arylacrylamide derivatives using cyclic oxime esters as radical sources followed by cyanoalkyl-mediated cyclization. This protocol features outstanding functional group compatibility, providing a variety of desired phenanthridine derivatives in moderate to good yields. Moreover, the application of a microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing reaction times to 10 min.

摘要

本研究描述了一种可见光诱导的级联反应,用于制备含氰烷基的多杂环化合物,该反应由 -芳基丙烯酰胺衍生物的光诱导自由基级联加成引发,使用环状肟酯作为自由基源,然后进行氰烷基介导的环化。该方案具有出色的官能团相容性,能够以中等至良好的收率提供多种所需的菲啶衍生物。此外,与等效的批量反应相比,微流技术的应用增强了这些反应,将反应时间显著缩短至 10 分钟。

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