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

Nantachai Inprung; Michael J James; Richard J K Taylor; William P Unsworth

doi:10.1021/acs.orglett.1c00205

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

Nantachai Inprung, Michael J James, Richard J K Taylor, William P Unsworth

Chemistry

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

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.

Original language	English
Pages (from-to)	2063-2068
Journal	Organic letters
Volume	23
Issue number	6
Early online date	1 Mar 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00205
Publication status	E-pub ahead of print - 1 Mar 2021

Bibliographical note

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Mon cascade paper version 18 revision
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Cite this

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AU - Unsworth, William P

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AB - 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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