Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol

From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products i...

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Autores principales: Fekete, Beáta, Palkó, Márta, Haukka, Matti, Fülöp, Ferenc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154686/
https://www.ncbi.nlm.nih.gov/pubmed/28406463
http://dx.doi.org/10.3390/molecules22040613
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author Fekete, Beáta
Palkó, Márta
Haukka, Matti
Fülöp, Ferenc
author_facet Fekete, Beáta
Palkó, Márta
Haukka, Matti
Fülöp, Ferenc
author_sort Fekete, Beáta
collection PubMed
description From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid.
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spelling pubmed-61546862018-11-13 Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol Fekete, Beáta Palkó, Márta Haukka, Matti Fülöp, Ferenc Molecules Article From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid. MDPI 2017-04-13 /pmc/articles/PMC6154686/ /pubmed/28406463 http://dx.doi.org/10.3390/molecules22040613 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
Fekete, Beáta
Palkó, Márta
Haukka, Matti
Fülöp, Ferenc
Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title_full Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title_fullStr Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title_full_unstemmed Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title_short Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
title_sort synthesis of pyrrolo[1,2-a]pyrimidine enantiomers via domino ring-closure followed by retro diels-alder protocol
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154686/
https://www.ncbi.nlm.nih.gov/pubmed/28406463
http://dx.doi.org/10.3390/molecules22040613
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