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

[Image: see text] 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 subs...

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Autores principales: Inprung, Nantachai, James, Michael J., Taylor, Richard J. K., Unsworth, William P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041380/
https://www.ncbi.nlm.nih.gov/pubmed/33645997
http://dx.doi.org/10.1021/acs.orglett.1c00205
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author Inprung, Nantachai
James, Michael J.
Taylor, Richard J. K.
Unsworth, William P.
author_facet Inprung, Nantachai
James, Michael J.
Taylor, Richard J. K.
Unsworth, William P.
author_sort Inprung, Nantachai
collection PubMed
description [Image: see text] 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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spelling pubmed-80413802021-04-13 A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines Inprung, Nantachai James, Michael J. Taylor, Richard J. K. Unsworth, William P. Org Lett [Image: see text] 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. American Chemical Society 2021-03-01 2021-03-19 /pmc/articles/PMC8041380/ /pubmed/33645997 http://dx.doi.org/10.1021/acs.orglett.1c00205 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Inprung, Nantachai
James, Michael J.
Taylor, Richard J. K.
Unsworth, William P.
A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title_full A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title_fullStr A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title_full_unstemmed A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title_short A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines
title_sort thiol-mediated three-step ring expansion cascade for the conversion of indoles into functionalized quinolines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041380/
https://www.ncbi.nlm.nih.gov/pubmed/33645997
http://dx.doi.org/10.1021/acs.orglett.1c00205
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