The Biginelli dihydropyrimidone synthesis using polyphosphate ester as a mild and efficient cyclocondensation/dehydration reagent

Falsone, S. Fabio; Kappe, C. Oliver

doi:10.3998/ark.5550190.0002.214

Cited by 48 publications

(9 citation statements)

References 7 publications

(9 reference statements)

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“…Results are given in Tables 4 and 5. A comparison with modern classic synthetic methods for dihydropyrimidinones and dihydropyridines [31,32] gives very good parameters (Figures 4 and 5).…”

Section: Synthesis Of 13-dihydropyrimidinonesmentioning

confidence: 92%

Sulfonated alumina: A suitable catalyst for furfural biomass building-block valorization through multicomponent reactions

et al. 2021

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Sulfonated alumina was synthetized and tested for the first time in furfural valorization through a multicomponent reaction for the preparation of a nitrogenated heterocyclic compound containing the furan substructure. Ten polysubstituted heterocycles, belonging to the dihydropyrimidinones (thiones) and 1,4-dihydropyridines, were obtained with very good yields (70% – 85%) using the tandem methodology and green reaction conditions. The catalyst was easily separated from the reaction medium, giving a high yield in the reusability studies. Green metrics were analyzed in order to consider the reaction suitability.

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“…Results are given in Tables 4 and 5. A comparison with modern classic synthetic methods for dihydropyrimidinones and dihydropyridines [31,32] gives very good parameters (Figures 4 and 5).…”

Section: Synthesis Of 13-dihydropyrimidinonesmentioning

confidence: 92%

Sulfonated alumina: A suitable catalyst for furfural biomass building-block valorization through multicomponent reactions

et al. 2021

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“…In 2001, Falsone and Kappeexplored the Biginelli reaction conditions and reported the polyphosphate ester (PPE) mediated condensation between ethyl acetoacetate 6, benzaldehydes 7, and urea 8 to achieve pyrimidin-2-ones 9 in good to excellent yields (Scheme 1). 14 It was observed that the use of PPE in THF solvent stabilized the N -acyliminium ion intermediates produced during the Biginelli reaction. Bicyclic 6-6 fused ring systems are well known due to their potent antipsychotic, analgesic, and antiasthmatic properties.…”

Section: Multicomponent Synthesismentioning

confidence: 99%

Recent synthetic methodologies for pyrimidine and its derivatives

Ibraheem¹,

Saddique²,

Aslam³

et al. 2018

Turk J Chem

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Pyrimidine derivatives are well known due to their remarkable pharmacological potential in various fields of science, and they are also present in some natural substances like DNA and RNA. These scaffolds manifest diversified biological activities such as antimicrobial, antiinflammatory, anti-HIV, antitubercular, antitumor, antineoplastic, and antimalarial. A pyrimidine ring is constructed when chalcones, amidines, guanidine, nitriles, isocyanates, urea, thiourea, and aminopyrazoles undergo condensation, coupling, or cyclization reactions. In this context, the present review illustrates a variety of novel and efficient synthetic approaches towards the synthesis of pyrimidine and its derivatives that were reported recently.

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“…The synthetic methodology used to create dipyrimidines has been well attested and has typically involved variations of the original Biginelli reaction [13][14][15][16]. However, this reaction often requests long reaction time, rough conditions, and affords low yield, particularly when substituted aliphatic and aromatic aldehydes are used.…”

Section: Introductionmentioning

confidence: 99%

One‐pot three‐component reaction; synthesis of new symmetrically bridge 4,4′‐(1,4‐phenylene)di‐pyrimidines under solvent free conditions

Mohamed

Abdelmeged

Shaker

et al. 2021

Journal of Heterocyclic Chem

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The present article describes a facile one-pot synthesis of a new series of 4,4 0 -(1,4-phenylene)-dipyrimidines (6a-c and 10a, b) by the reaction of terephthalaldehyde (1), 2-acetylthiophene, and/or nitriles with Sbenzylthiouronium chloride 3a. And also, the di-pyrimidinones 13a-d were obtained by the reaction of different amidines 3a-d and ethyl cyanoacetate (11) with terephthalaldehyde (1) under solvent-free conditions in the existence of sodium hydroxide which is found to be a more efficient base for these reactions. The final products were characterized by spectral data and elemental analysis, IR, MS, 1 H, and 13 C NMR spectroscopy.

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The Biginelli dihydropyrimidone synthesis using polyphosphate ester as a mild and efficient cyclocondensation/dehydration reagent

Cited by 48 publications

References 7 publications

Sulfonated alumina: A suitable catalyst for furfural biomass building-block valorization through multicomponent reactions

Sulfonated alumina: A suitable catalyst for furfural biomass building-block valorization through multicomponent reactions

Recent synthetic methodologies for pyrimidine and its derivatives

One‐pot three‐component reaction; synthesis of new symmetrically bridge 4,4′‐(1,4‐phenylene)di‐pyrimidines under solvent free conditions

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