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Regioselective Reduction of 1H-1,2,3-Triazole Diesters
Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. T...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8469956/ https://www.ncbi.nlm.nih.gov/pubmed/34577060 http://dx.doi.org/10.3390/molecules26185589 |
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author | Butler, Christopher R. Bendesky, Justin Schoffstall, Allen Milton |
author_facet | Butler, Christopher R. Bendesky, Justin Schoffstall, Allen Milton |
author_sort | Butler, Christopher R. |
collection | PubMed |
description | Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding. |
format | Online Article Text |
id | pubmed-8469956 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-84699562021-09-27 Regioselective Reduction of 1H-1,2,3-Triazole Diesters Butler, Christopher R. Bendesky, Justin Schoffstall, Allen Milton Molecules Article Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding. MDPI 2021-09-15 /pmc/articles/PMC8469956/ /pubmed/34577060 http://dx.doi.org/10.3390/molecules26185589 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Butler, Christopher R. Bendesky, Justin Schoffstall, Allen Milton Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title | Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title_full | Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title_fullStr | Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title_full_unstemmed | Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title_short | Regioselective Reduction of 1H-1,2,3-Triazole Diesters |
title_sort | regioselective reduction of 1h-1,2,3-triazole diesters |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8469956/ https://www.ncbi.nlm.nih.gov/pubmed/34577060 http://dx.doi.org/10.3390/molecules26185589 |
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