One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones/‐thiones Catalyzed by Zinc Chloride: An Improved Procedure for the Biginelli Reaction Using Microwaves under Solvent‐Free Condition.

Päsha, M. A.; Swamy, N. Ramachandra; Jayäshankara, V. P.

doi:10.1002/chin.200534209

Cited by 8 publications

(10 citation statements)

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“…The present protocol provides a high yielding, efficient and improved route for the synthesis of dihydropyrimidinones. Further, Co(II)Pc 5 catalyst is better than the usual H + , ZnCl 2 and ammonium salt catalysts used previously for the synthesis of (DHPMs) [32,33]. …”

Section: Resultsmentioning

confidence: 99%

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

et al. 2017

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In this study, novel phthalonitrile 3 and their corresponding metal-free 4 and metallophthalocyanine derivatives 5–7 bearing 2-isopropenyl-4-methoxy-1-methylbenzene groups were synthesized and characterized. 3,4-Dihydropyrimidinones have been synthesized by a modified Biginelli-type reaction with various metallophthalocyanines 5–7 as catalysts. Compared to the classical Biginielli reaction, the new method has the advantages of good yield and short reaction time. Among the various metallophthalocyanines studied, cobalt (II)-phthalocyanine was found to be most active for this transformation. The newly prepared compounds were characterized using elemental analyses, MS, IR, 1H/13C-NMR and UV-Vis spectroscopy. In addition; the 3,4-dihydropyrimidinones (DHPMs) 8–12 were investigated for antimicrobial activities and revealed good activity. The minimum inhibitory concentration (MIC) was determined by the microdilution technique in Mueller-Hinton broth. The MICs were recorded after 24 hours of incubation at 37 °C. These results are promising, showing these compounds are biologically active.

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Section: Resultsmentioning

confidence: 99%

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

et al. 2017

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“…Certain 3,4-dihydropyrimidines have developed as essential props of numerous calcium antihypertensive agents, adrenergic, channel blockers, and neuropeptide antagonists. 24 A number of natural marine products accommodate the 3,4-dihydropyrimidine nucleus, described in the literature for remarkable anti-HIV alkaloid batzelladine B activities (Figure 1). 25,26…”

Section: Introductionmentioning

confidence: 99%

Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate

et al. 2019

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The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted Biginelli protocol has been developed for the first time by a successive one-pot three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate, and thiourea/urea to afford pharmacologically promising 1,2,3,4-tetrahydropyrimidines in high yields at room temperature. The key benefits of the present scheme are the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst, and solvent-free conditions, thus providing economic and environmental advantages. In addition, a series of 4-oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles analogues were synthesized and selected for their in vitro antifungal and antibacterial activities.

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“…This has lead to the development of several new methodologies, which improve the yields compared to original procedure. These new strategies involve the combinations of Lewis acids and/or transition metal salts, for example, BF 3 ·OEt 2 , montmorillonite (KSF), polyphosphate esters, and reagents like InCl 3 [ 9 ], LiBr [ 10 ], TMSCl/NaI [ 11 ], LaCl 3 ·7H 2 O [ 12 ], CeCl 3 ·7H 2 O [ 13 ], Mn(OAc) 3 ·2H 2 O [ 14 ], InBr [ 15 ], FeCl 3 and HCl [ 16 ], ytterbium triflate [ 17 ], Iodine [ 18 ], ZnCl 2 [ 19 ], CoCl 2 [ 20 ], and so forth. Many Lewis acids and transition metal salts have been found to catalyze this reaction, but they still have limitations like high cost, limited availability, prolonged reaction duration, and the use of strong acids.…”

Section: Introductionmentioning

confidence: 99%

Lithium-Acetate-Mediated Biginelli One-Pot Multicomponent Synthesis under Solvent-Free Conditions and Cytotoxic Activity against the Human Lung Cancer Cell Line A549 and Breast Cancer Cell Line MCF7

Sachdeva

Dwivedi

2012

The Scientific World Journal

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Various Biginelli compounds (dihydropyrimidinones) have been synthesized efficiently and in high yields under mild, solvent-free, and eco-friendly conditions in a one-pot reaction of 1,3-dicarbonyl compounds, aldehydes, and urea/thiourea/acetyl thiourea using lithium-acetate as a novel catalyst without the addition of any proton source. Comparative catalytic efficiency of lithium-acetate and polyphosphoric acid to catalyze Biginelli condensation is also studied under neat conditions. The reaction is carried out in the absence of any solvent and represents an improvement of the classical Biginelli protocol and an advantage in comparison with FeCl3 ·6H2O, NiCl2 ·6H2O and CoCl2 ·6H2O that were used with HCl as a cocatalyst. Compared to classical Biginelli reaction conditions, the present method has advantages of good yields, short reaction times, and experimental simplicity. The obtained products have been identified by spectral (1H NMR and IR) data and their melting points. The prepared compounds are evaluated for anticancer activity against two human cancer cell lines (lung cancer cell line A549 and breast cancer cell line MCF7).

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One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones/‐thiones Catalyzed by Zinc Chloride: An Improved Procedure for the Biginelli Reaction Using Microwaves under Solvent‐Free Condition.

Cited by 8 publications

References 0 publications

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity

Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate

Lithium-Acetate-Mediated Biginelli One-Pot Multicomponent Synthesis under Solvent-Free Conditions and Cytotoxic Activity against the Human Lung Cancer Cell Line A549 and Breast Cancer Cell Line MCF7

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