The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction

Puripat, Maneeporn; Ramozzi, Romain; Hatanaka, Miho; Parasuk, Waraporn; Parasuk, Vudhichai; Morokuma, Keiji

doi:10.1021/acs.joc.5b00407

Cited by 104 publications

(49 citation statements)

References 84 publications

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“…The mechanism of the Biginelli reaction, using acidic Brönsted or Lewis catalysts, was discussed by several authors [13,21,22]. Kappe [23,24], re-examining this question concluded that the first step in this mechanism:" involves the acid-catalysed formation of an N-acyliminium ion precursor from and aldehyde and urea component".…”

Section: Introductionmentioning

confidence: 99%

Calcium, Barium and Strontium apatites: A new generation of catalysts in the Biginelli reaction

et al. 2017

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Section: Introductionmentioning

confidence: 99%

Calcium, Barium and Strontium apatites: A new generation of catalysts in the Biginelli reaction

et al. 2017

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“…Metal‐based heterogeneous catalysts such as polymers supported metal nanoparticles, ionic liquids, zeolites, acidic surfactants, ion exchange resins, Lewis acids, metal nanoparticles, urea, silica supported sulfonated graphene oxide, etc. are reported . Rate enhancement using ultrasound as well as microwaves is also been reported.…”

Section: Introductionmentioning

confidence: 90%

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

et al. 2017

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The effect of varying degree of oxidation of graphene oxide on its catalytic activity for synthesis of dihydropyrimidinones via Biginelli reaction is investigated. Graphene oxide with varying degree of oxidation (GO‐x) was synthesized, and characterized to confirm the change in functional groups on GO surface with different amount of oxidizing agent used during synthesis. An increase in amount of oxidant, increases the percentage of oxygen in GO‐x, increasing the d‐spacing and thus enhancing the exfoliation of GO‐x. The carboxylic acid groups increase with increasing oxidation degree, while the proportion of hydroxyl groups is almost the same. GO‐x shows excellent activity towards catalysing Biginelli reaction. An increase in oxygen content in GO‐x improves its catalytic activity, which is attributed to the increased acidity in GO‐x. Reaction kinetics imply a second order reaction. GO‐x shows excellent recyclability with only marginal loss in activity on recycle.

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“…Compound 5 was synthesized by the four components Biginelli-like cyclocondensation reaction of tert -butyl β-ketoester (1.0 mmol) ( 1 ), propargyl alcohol (1.2 mmol) ( 2 ), substituted aryl aldehyde (1.0 mmol) ( 3 ), and urea (1.2 mmol) ( 4 ) by a reflux method 39. The entire reaction mixture was allowed to stir for 3 hours at room temperature along with a catalytic amount of Cu(OAc) 2 (0.1 mmol) and sodium ascorbate (0.2 mmol) in a 1:2 ratio of acetone and water (2 mL) as a solvent till the reaction was complete.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

Venugopala¹,

Rao²,

Bhandary³

et al. 2016

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The novel (1-(4-aryl)-1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were synthesized by the click reaction of the dihydropyrimidinones, bearing a terminal alkynyl group, with various substituted aryl azides at room temperature using a catalytic amount of Cu(OAc)2 and sodium ascorbate in a 1:2 ratio of acetone and water as a solvent. The newly synthesized compounds were characterized by a number of spectroscopic techniques, such as infrared, liquid chromatography-mass spectrometry, 1H, and 13C nuclear magnetic resonance along with single crystal X-ray diffraction. The current procedure for the synthesis of 1,2,3-triazole hybrids with dihydropyrimidinones is appropriate for the synthesis of a library of analogs 7a-l and the method accessible here is operationally simple and has excellent yields. The title compounds 7a-l were evaluated for their in vitro antitubercular activity against H37RV and multidrug-resistant strains of Mycobacterium tuberculosis by resazurin microplate assay plate method and it was found that compound 7d was promising against H37RV and multidrug-resistant strains of M. tuberculosis at 10 and 15 μg/mL, respectively.

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The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction

Cited by 104 publications

References 84 publications

Calcium, Barium and Strontium apatites: A new generation of catalysts in the Biginelli reaction

Calcium, Barium and Strontium apatites: A new generation of catalysts in the Biginelli reaction

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

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