Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes

[Image: see text] Acylcyclopropanes are employed as useful donor–acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 position...

Descripción completa

Detalles Bibliográficos
Autores principales: Ortega, Alesandere, Uria, Uxue, Tejero, Tomás, Prieto, Liher, Reyes, Efraim, Merino, Pedro, Vicario, Jose L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490874/
https://www.ncbi.nlm.nih.gov/pubmed/33689377
http://dx.doi.org/10.1021/acs.orglett.1c00470
_version_ 1784793176321556480
author Ortega, Alesandere
Uria, Uxue
Tejero, Tomás
Prieto, Liher
Reyes, Efraim
Merino, Pedro
Vicario, Jose L.
author_facet Ortega, Alesandere
Uria, Uxue
Tejero, Tomás
Prieto, Liher
Reyes, Efraim
Merino, Pedro
Vicario, Jose L.
author_sort Ortega, Alesandere
collection PubMed
description [Image: see text] Acylcyclopropanes are employed as useful donor–acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole and provides access to the 8,9-dihydropyrido[1,2-a]indole scaffold that is the central core of several biologically relevant indole alkaloids in excellent yields and good selectivities.
format Online
Article
Text
id pubmed-9490874
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-94908742022-09-22 Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes Ortega, Alesandere Uria, Uxue Tejero, Tomás Prieto, Liher Reyes, Efraim Merino, Pedro Vicario, Jose L. Org Lett [Image: see text] Acylcyclopropanes are employed as useful donor–acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole and provides access to the 8,9-dihydropyrido[1,2-a]indole scaffold that is the central core of several biologically relevant indole alkaloids in excellent yields and good selectivities. American Chemical Society 2021-03-09 2021-03-19 /pmc/articles/PMC9490874/ /pubmed/33689377 http://dx.doi.org/10.1021/acs.orglett.1c00470 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/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 Ortega, Alesandere
Uria, Uxue
Tejero, Tomás
Prieto, Liher
Reyes, Efraim
Merino, Pedro
Vicario, Jose L.
Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title_full Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title_fullStr Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title_full_unstemmed Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title_short Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes
title_sort brønsted acid catalyzed (4 + 2) cyclocondensation of 3-substituted indoles with donor–acceptor cyclopropanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490874/
https://www.ncbi.nlm.nih.gov/pubmed/33689377
http://dx.doi.org/10.1021/acs.orglett.1c00470
work_keys_str_mv AT ortegaalesandere brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT uriauxue brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT tejerotomas brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT prietoliher brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT reyesefraim brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT merinopedro brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes
AT vicariojosel brønstedacidcatalyzed42cyclocondensationof3substitutedindoleswithdonoracceptorcyclopropanes

Ejemplares similares