Int. J. Mol. Sci. 2013, 14(2), 2903-2915; doi:10.3390/ijms14022903
Article

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

Received: 7 November 2012; in revised form: 19 December 2012 / Accepted: 4 January 2013 / Published: 30 January 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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