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一种基于巯基介导的三步环扩张级联反应，实现吲哚到功能化喹啉的转化。

A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.

机构信息

Department of Chemistry, University of York, Heslington, York, U.K.., YO10 5DD.

出版信息

Org Lett. 2021 Mar 19;23(6):2063-2068. doi: 10.1021/acs.orglett.1c00205. Epub 2021 Mar 1.

DOI:10.1021/acs.orglett.1c00205
PMID:33645997
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8041380/
Abstract

An operationally simple, high yielding three-step cascade process is described for the direct conversion of indole-tethered ynones into functionalized quinolines. A single "multitasking" thiol reagent is used to promote a three-step dearomatizing spirocyclization, nucleophilic substitution, and one-atom ring expansion reaction cascade under remarkably mild conditions. In addition, a novel route to thio-oxindoles is described, which was discovered by serendipity.

摘要

本文描述了一种操作简单、产率高的三步级联反应，可将吲哚连接的 ynones 直接转化为功能化的喹啉。一种单一的“多任务”硫醇试剂被用来在非常温和的条件下促进三步 dearomatizing 螺环化、亲核取代和单原子环扩张反应级联。此外，还描述了一种通过偶然发现的新型硫代-氧杂吲哚合成路线。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/8c7e3f63969a/ol1c00205_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/8ab02e65c33e/ol1c00205_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/0f9f507427cd/ol1c00205_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/81e0b442169e/ol1c00205_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/8c7e3f63969a/ol1c00205_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/8ab02e65c33e/ol1c00205_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/0f9f507427cd/ol1c00205_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/81e0b442169e/ol1c00205_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22ef/8041380/8c7e3f63969a/ol1c00205_0004.jpg

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