A General and Scalable Synthesis of Polysubstituted Indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of...

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Autores principales: Tejedor, David, Diana-Rivero, Raquel, García-Tellado, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730962/
https://www.ncbi.nlm.nih.gov/pubmed/33260745
http://dx.doi.org/10.3390/molecules25235595
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author Tejedor, David
Diana-Rivero, Raquel
García-Tellado, Fernando
author_facet Tejedor, David
Diana-Rivero, Raquel
García-Tellado, Fernando
author_sort Tejedor, David
collection PubMed
description A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.
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spelling pubmed-77309622020-12-12 A General and Scalable Synthesis of Polysubstituted Indoles Tejedor, David Diana-Rivero, Raquel García-Tellado, Fernando Molecules Article A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies. MDPI 2020-11-28 /pmc/articles/PMC7730962/ /pubmed/33260745 http://dx.doi.org/10.3390/molecules25235595 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tejedor, David
Diana-Rivero, Raquel
García-Tellado, Fernando
A General and Scalable Synthesis of Polysubstituted Indoles
title A General and Scalable Synthesis of Polysubstituted Indoles
title_full A General and Scalable Synthesis of Polysubstituted Indoles
title_fullStr A General and Scalable Synthesis of Polysubstituted Indoles
title_full_unstemmed A General and Scalable Synthesis of Polysubstituted Indoles
title_short A General and Scalable Synthesis of Polysubstituted Indoles
title_sort general and scalable synthesis of polysubstituted indoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730962/
https://www.ncbi.nlm.nih.gov/pubmed/33260745
http://dx.doi.org/10.3390/molecules25235595
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