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Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-d...

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Autores principales: Martínez, Joel, Romero-Vega, Stephany, Abeja-Cruz, Rita, Álvarez-Toledano, Cecilio, Miranda, René
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588021/
https://www.ncbi.nlm.nih.gov/pubmed/23364612
http://dx.doi.org/10.3390/ijms14022903
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author Martínez, Joel
Romero-Vega, Stephany
Abeja-Cruz, Rita
Álvarez-Toledano, Cecilio
Miranda, René
author_facet Martínez, Joel
Romero-Vega, Stephany
Abeja-Cruz, Rita
Álvarez-Toledano, Cecilio
Miranda, René
author_sort Martínez, Joel
collection PubMed
description Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%–7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%–17% in 12 h, and microwave irradiation, yield 18%–80%, requiring very low reaction times of 0.25–0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures ((1)H, (11)B, and (13)C NMR, FAB(+)MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB(+)-mode, enabled unequivocal characterization of the target molecules.
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spelling pubmed-35880212013-03-13 Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters Martínez, Joel Romero-Vega, Stephany Abeja-Cruz, Rita Álvarez-Toledano, Cecilio Miranda, René Int J Mol Sci Article Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%–7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%–17% in 12 h, and microwave irradiation, yield 18%–80%, requiring very low reaction times of 0.25–0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures ((1)H, (11)B, and (13)C NMR, FAB(+)MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB(+)-mode, enabled unequivocal characterization of the target molecules. MDPI 2013-01-30 /pmc/articles/PMC3588021/ /pubmed/23364612 http://dx.doi.org/10.3390/ijms14022903 Text en © 2013 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Martínez, Joel
Romero-Vega, Stephany
Abeja-Cruz, Rita
Álvarez-Toledano, Cecilio
Miranda, René
Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title_full Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title_fullStr Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title_full_unstemmed Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title_short Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
title_sort green approach—multicomponent production of boron—containing hantzsch and biginelli esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588021/
https://www.ncbi.nlm.nih.gov/pubmed/23364612
http://dx.doi.org/10.3390/ijms14022903
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