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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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Detalles Bibliográficos
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
Descripción
Sumario: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.