Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines

Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines via a Lewis acid-catalyzed domino ring-opening with concomitant ring annulation using activated spiro-aziridines and heteroarenes. This method offers a new class of...

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Autores principales: Bhandari, Sonal, Sana, Sravani, Lahoti, Vandana, Tokala, Ramya, Shankaraiah, Nagula
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9052938/
https://www.ncbi.nlm.nih.gov/pubmed/35493670
http://dx.doi.org/10.1039/d0ra00684j
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author Bhandari, Sonal
Sana, Sravani
Lahoti, Vandana
Tokala, Ramya
Shankaraiah, Nagula
author_facet Bhandari, Sonal
Sana, Sravani
Lahoti, Vandana
Tokala, Ramya
Shankaraiah, Nagula
author_sort Bhandari, Sonal
collection PubMed
description Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines via a Lewis acid-catalyzed domino ring-opening with concomitant ring annulation using activated spiro-aziridines and heteroarenes. This method offers a new class of novel spiro-fused polycyclic pyrrolidines in a one-pot and sustainable manner with good yields and high diastereoselectivity. In addition, the structure of 3d was confirmed by single X-ray crystallography analysis.
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spelling pubmed-90529382022-04-29 Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines Bhandari, Sonal Sana, Sravani Lahoti, Vandana Tokala, Ramya Shankaraiah, Nagula RSC Adv Chemistry Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines via a Lewis acid-catalyzed domino ring-opening with concomitant ring annulation using activated spiro-aziridines and heteroarenes. This method offers a new class of novel spiro-fused polycyclic pyrrolidines in a one-pot and sustainable manner with good yields and high diastereoselectivity. In addition, the structure of 3d was confirmed by single X-ray crystallography analysis. The Royal Society of Chemistry 2020-04-24 /pmc/articles/PMC9052938/ /pubmed/35493670 http://dx.doi.org/10.1039/d0ra00684j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Bhandari, Sonal
Sana, Sravani
Lahoti, Vandana
Tokala, Ramya
Shankaraiah, Nagula
Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title_full Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title_fullStr Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title_full_unstemmed Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title_short Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
title_sort ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9052938/
https://www.ncbi.nlm.nih.gov/pubmed/35493670
http://dx.doi.org/10.1039/d0ra00684j
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