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Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters
Department of Chemistry, Faculty of Superior Studies Cuautitlan, Field 1, Autonomous National University of Mexico, Cuautitlan Izcalli, State of Mexico, 54740, Mexico
Institute of Chemistry, Autonomous National University of Mexico, University City, Coyoacan, D.F., 04510, Mexico
* Author to whom correspondence should be addressed.
Received: 7 November 2012; in revised form: 19 December 2012 / Accepted: 4 January 2013 / Published: 30 January 2013
Abstract: 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 (1H, 11B, and 13C 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.
Keywords: multicomponent reaction; green chemistry; twelve principles; boron-containing-Hantzsch and Biginelli esters; microwave and infrared irradiation; matrix-ion interaction; FAB+MS
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Martínez, J.; Romero-Vega, S.; Abeja-Cruz, R.; Álvarez-Toledano, C.; Miranda, R. Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters. Int. J. Mol. Sci. 2013, 14, 2903-2915.
Martínez J, Romero-Vega S, Abeja-Cruz R, Álvarez-Toledano C, Miranda R. Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters. International Journal of Molecular Sciences. 2013; 14(2):2903-2915.
Martínez, Joel; Romero-Vega, Stephany; Abeja-Cruz, Rita; Álvarez-Toledano, Cecilio; Miranda, René. 2013. "Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters." Int. J. Mol. Sci. 14, no. 2: 2903-2915.