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

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Article in Organic Letters

From the same journal

Organic Letters (Journal)
Lianne Irene Willems (Reviewer)
16 Sep 2018
Activity: Publication peer-review and editorial work › Journal peer review

Research output: Contribution to journal › Article › peer-review

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Published copy (DOI)

10.1021/acs.orglett.1c00205

Author(s)

Department/unit(s)

Chemistry

Publication details

Journal	Organic letters
Date	Accepted/In press - 24 Feb 2021
Date	E-pub ahead of print (current) - 1 Mar 2021
Early online date	1/03/21
Original language	English

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.

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