The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles

Nitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today’s most desirable synthetic targets and the Povarov reaction is a powerful sy...

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Autores: Masdeu Margalef, Carme, De los Santos Ruiz, Jesús Manuel, Palacios Gambra, Francisco Javier, Alonso Pérez, Concepción Estibaliz
Tipo de documento: artigo
Data de publicação:2023
País:España
Recursos:Universidad del País Vasco
Repositório:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/61799
Acesso em linha:http://hdl.handle.net/10810/61799
Access Level:Acceso aberto
Palavra-chave:Povarov reaction
intramolecular
fused nitrogenated heterocycles
[4 + 2]-cycloaddition
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spelling The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing HeterocyclesMasdeu Margalef, CarmeDe los Santos Ruiz, Jesús ManuelPalacios Gambra, Francisco JavierAlonso Pérez, Concepción EstibalizPovarov reactionintramolecularfused nitrogenated heterocycles[4 + 2]-cycloadditionNitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today’s most desirable synthetic targets and the Povarov reaction is a powerful synthetic tool for the construction of highly functionalized heterocyclic systems. This process involves an aromatic amine, a carbonyl compound, and an olefin or acetylene to give rise to the formation of a nitrogen-containing heterocycle. This review illustrates advances in the synthetic aspects of the intramolecular Povarov reaction for the construction of intricate nitrogen-containing polyheterocyclic compounds. This original review presents research done in this field, with references to important works by internationally relevant research groups on this current topic, covering the literature from 1992 to 2022. The intramolecular Povarov reactions are described here according to the key processes involved, using different combinations of aromatic or heteroaromatic amines, and aliphatic, aromatic, or heteroaromatic aldehydes. Some catalytic reactions promoted by transition metals are detailed, as well as the oxidative Povarov reaction and some asymmetric intramolecular Povarov processes.Financial support from the Ministerio de Ciencia, Innovación y Universidades (MCIU) (PID2021-122558OB-I00, UE), by Gobierno Vasco, Universidad del País Vasco (GV, IT1701- 22; UPV) and by Fundación Vital (VITAL21/01) is gratefully acknowledged. Open Access funding provided thanks to the CRUE-CSIC agreement with Springer NatureSpringer202320232023info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/61799reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MICINN/PID2021-122558OB-I00/https://link.springer.com/article/10.1007/s41061-023-00428-7info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/© The Author(s) 2023. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.Atribución 3.0 Españaoai:addi.ehu.eus:10810/617992026-06-18T09:23:17Z
dc.title.none.fl_str_mv The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
title The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
spellingShingle The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
Masdeu Margalef, Carme
Povarov reaction
intramolecular
fused nitrogenated heterocycles
[4 + 2]-cycloaddition
title_short The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
title_full The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
title_fullStr The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
title_full_unstemmed The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
title_sort The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles
dc.creator.none.fl_str_mv Masdeu Margalef, Carme
De los Santos Ruiz, Jesús Manuel
Palacios Gambra, Francisco Javier
Alonso Pérez, Concepción Estibaliz
author Masdeu Margalef, Carme
author_facet Masdeu Margalef, Carme
De los Santos Ruiz, Jesús Manuel
Palacios Gambra, Francisco Javier
Alonso Pérez, Concepción Estibaliz
author_role author
author2 De los Santos Ruiz, Jesús Manuel
Palacios Gambra, Francisco Javier
Alonso Pérez, Concepción Estibaliz
author2_role author
author
author
dc.subject.none.fl_str_mv Povarov reaction
intramolecular
fused nitrogenated heterocycles
[4 + 2]-cycloaddition
topic Povarov reaction
intramolecular
fused nitrogenated heterocycles
[4 + 2]-cycloaddition
description Nitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today’s most desirable synthetic targets and the Povarov reaction is a powerful synthetic tool for the construction of highly functionalized heterocyclic systems. This process involves an aromatic amine, a carbonyl compound, and an olefin or acetylene to give rise to the formation of a nitrogen-containing heterocycle. This review illustrates advances in the synthetic aspects of the intramolecular Povarov reaction for the construction of intricate nitrogen-containing polyheterocyclic compounds. This original review presents research done in this field, with references to important works by internationally relevant research groups on this current topic, covering the literature from 1992 to 2022. The intramolecular Povarov reactions are described here according to the key processes involved, using different combinations of aromatic or heteroaromatic amines, and aliphatic, aromatic, or heteroaromatic aldehydes. Some catalytic reactions promoted by transition metals are detailed, as well as the oxidative Povarov reaction and some asymmetric intramolecular Povarov processes.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/61799
url http://hdl.handle.net/10810/61799
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MICINN/PID2021-122558OB-I00/
https://link.springer.com/article/10.1007/s41061-023-00428-7
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
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