A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters

A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-additio...

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Autores principales: Shikhaliev, Khidmet, Sabynin, Artem, Sekirin, Valeri, Krysin, Michael, Zubkov, Fedor, Yankina, Kristina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150208/
https://www.ncbi.nlm.nih.gov/pubmed/29165400
http://dx.doi.org/10.3390/molecules22112035
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author Shikhaliev, Khidmet
Sabynin, Artem
Sekirin, Valeri
Krysin, Michael
Zubkov, Fedor
Yankina, Kristina
author_facet Shikhaliev, Khidmet
Sabynin, Artem
Sekirin, Valeri
Krysin, Michael
Zubkov, Fedor
Yankina, Kristina
author_sort Shikhaliev, Khidmet
collection PubMed
description A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular nucleophilic addition without recyclyzation of imide cycle.
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spelling pubmed-61502082018-11-13 A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters Shikhaliev, Khidmet Sabynin, Artem Sekirin, Valeri Krysin, Michael Zubkov, Fedor Yankina, Kristina Molecules Article A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular nucleophilic addition without recyclyzation of imide cycle. MDPI 2017-11-22 /pmc/articles/PMC6150208/ /pubmed/29165400 http://dx.doi.org/10.3390/molecules22112035 Text en © 2017 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
Shikhaliev, Khidmet
Sabynin, Artem
Sekirin, Valeri
Krysin, Michael
Zubkov, Fedor
Yankina, Kristina
A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title_full A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title_fullStr A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title_full_unstemmed A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title_short A New Synthetic Route to Polyhydrogenated Pyrrolo[3,4-b]pyrroles by the Domino Reaction of 3-Bromopyrrole-2,5-Diones with Aminocrotonic Acid Esters
title_sort new synthetic route to polyhydrogenated pyrrolo[3,4-b]pyrroles by the domino reaction of 3-bromopyrrole-2,5-diones with aminocrotonic acid esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150208/
https://www.ncbi.nlm.nih.gov/pubmed/29165400
http://dx.doi.org/10.3390/molecules22112035
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