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Quantum Reality in the Selective Reduction of a Benzofuran System

Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical cal...

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Autores principales: Coaviche-Yoval, Arturo, Andrade-Jorge, Erik, Pérez-González, Cuauhtémoc, Luna, Héctor, Tovar-Miranda, Ricardo, Trujillo-Ferrara, José G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600454/
https://www.ncbi.nlm.nih.gov/pubmed/31151186
http://dx.doi.org/10.3390/molecules24112061
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author Coaviche-Yoval, Arturo
Andrade-Jorge, Erik
Pérez-González, Cuauhtémoc
Luna, Héctor
Tovar-Miranda, Ricardo
Trujillo-Ferrara, José G.
author_facet Coaviche-Yoval, Arturo
Andrade-Jorge, Erik
Pérez-González, Cuauhtémoc
Luna, Héctor
Tovar-Miranda, Ricardo
Trujillo-Ferrara, José G.
author_sort Coaviche-Yoval, Arturo
collection PubMed
description Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson’s hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ω(k)) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (P(k)(+)) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction.
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spelling pubmed-66004542019-07-16 Quantum Reality in the Selective Reduction of a Benzofuran System Coaviche-Yoval, Arturo Andrade-Jorge, Erik Pérez-González, Cuauhtémoc Luna, Héctor Tovar-Miranda, Ricardo Trujillo-Ferrara, José G. Molecules Article Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson’s hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ω(k)) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (P(k)(+)) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction. MDPI 2019-05-30 /pmc/articles/PMC6600454/ /pubmed/31151186 http://dx.doi.org/10.3390/molecules24112061 Text en © 2019 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
Coaviche-Yoval, Arturo
Andrade-Jorge, Erik
Pérez-González, Cuauhtémoc
Luna, Héctor
Tovar-Miranda, Ricardo
Trujillo-Ferrara, José G.
Quantum Reality in the Selective Reduction of a Benzofuran System
title Quantum Reality in the Selective Reduction of a Benzofuran System
title_full Quantum Reality in the Selective Reduction of a Benzofuran System
title_fullStr Quantum Reality in the Selective Reduction of a Benzofuran System
title_full_unstemmed Quantum Reality in the Selective Reduction of a Benzofuran System
title_short Quantum Reality in the Selective Reduction of a Benzofuran System
title_sort quantum reality in the selective reduction of a benzofuran system
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600454/
https://www.ncbi.nlm.nih.gov/pubmed/31151186
http://dx.doi.org/10.3390/molecules24112061
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