Phenylboronic Acid as a Mild and Efficient Catalyst for Biginelli Reaction.

Debache, Abdelmadjid; Boumoud, Boudjemaa; Amimour, Mouna; Belfaitah, Ali; Rhouati, Salah; Carboni, Bertrand

doi:10.1002/chin.200647171

Cited by 2 publications

(2 citation statements)

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“…In the production of the BCDHPm esters, urea does not reach its decomposition temperature (160 °C), therefore toxic by-products (biuret, carbon dioxide, and cyanuric acid), are not generated, supporting the first, third, and twelfth green chemistry principles. Finally, with regard to the moderate yields of the BCDHPm esters, it can be assumed that an interaction occurs between formylphenylboronic acid and urea (a) or 1,3-ciclohexanedione (b), either by protonation or coordination with the boronic moiety, Scheme 3, according to Debache et al [26]. …”

Section: Resultsmentioning

confidence: 99%

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

Martínez

Romero-Vega

Abeja-Cruz

et al. 2013

IJMS

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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.

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Section: Resultsmentioning

confidence: 99%

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

Martínez

Romero-Vega

Abeja-Cruz

et al. 2013

IJMS

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show abstract

“…Phenyl boronic acid [31] was reported to catalyse the Biginelli reaction in acetonitrile solvent under refluxing conditions for 18 h. Ammonium chloride [32] solid-supported solvent-free synthesis of 3,4-dihydropyrimidin-2(1 H )-ones at 100°C is also reported. Green approach via polystyrene sulfonic acid [33] is also reported under microwave heating at 80°C and via TaBr 5 [34] catalyst at 75°C.…”

Section: Introductionmentioning

confidence: 99%