Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of th...

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Detalles Bibliográficos
Autores principales: Mortén, Magnus, Hennum, Martin, Bonge-Hansen, Tore
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661008/
https://www.ncbi.nlm.nih.gov/pubmed/26664614
http://dx.doi.org/10.3762/bjoc.11.210
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author Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
author_facet Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
author_sort Mortén, Magnus
collection PubMed
description In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H–X.
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spelling pubmed-46610082015-12-09 Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates Mortén, Magnus Hennum, Martin Bonge-Hansen, Tore Beilstein J Org Chem Letter In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H–X. Beilstein-Institut 2015-10-20 /pmc/articles/PMC4661008/ /pubmed/26664614 http://dx.doi.org/10.3762/bjoc.11.210 Text en Copyright © 2015, Mortén et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Mortén, Magnus
Hennum, Martin
Bonge-Hansen, Tore
Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title_full Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title_fullStr Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title_full_unstemmed Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title_short Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
title_sort synthesis of quinoline-3-carboxylates by a rh(ii)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661008/
https://www.ncbi.nlm.nih.gov/pubmed/26664614
http://dx.doi.org/10.3762/bjoc.11.210
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AT bongehansentore synthesisofquinoline3carboxylatesbyarhiicatalyzedcyclopropanationringexpansionreactionofindoleswithhalodiazoacetates

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