Efficient Biginelli Reaction Catalyzed by Sulfamic Acid or Silica Sulfuric Acid under Solvent‐Free Conditions

Chen, Wei‐Yi; Qin, Su‐Dong; Jin, Jian

doi:10.1080/00397910600977632

Cited by 33 publications

(5 citation statements)

References 28 publications

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“…In addition, sulfamic acid was also employed as a catalyst. The reaction mixture including the Biginelli reagents and SSA catalyst was heated to yield high to excellent amount of DHPMs . The solvent free reaction, high to excellent yields and short reaction time strikes the contribution of said protocol to the development of the Biginelli reaction.…”

Section: Inorganic Polymersmentioning

confidence: 99%

Biginelli Reaction: Polymer Supported Catalytic Approaches

et al. 2019

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The Biginelli product, dihydropyrimidinone (DHPM) core, and its derivatives are of immense biological importance. There are several methods reported as modifications to the original Biginelli reaction. Among them, many involve the use of different catalysts. Also, among the advancements that have been made to the Biginelli reaction, improvements in product yields, less hazardous reaction conditions, and simplified isolation of products from the reaction predominate. Recently, solid-phase synthetic protocols have attracted the research community for improved yields, simplified product purification, recyclability of the solid support, which forms a special economic approach for Biginelli reaction. The present Review highlights the role of polymer-supported catalysts in Biginelli reaction, which may involve organic, inorganic, or hybrid polymers as support for catalysts. A few of the schemes involve magnetically recoverable catalysts where work up provides green approach relative to traditional methods. Some research groups used polymer−catalyst nanocomposites and polymer-supported ionic liquids as catalyst. Solvent-free, an ultrasound or microwave-assisted Biginelli reactions with polymer-supported catalysts are also reported.

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Section: Inorganic Polymersmentioning

confidence: 99%

Biginelli Reaction: Polymer Supported Catalytic Approaches

et al. 2019

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“…It has been found that assorted catalysts and several methods were employed for the same. Many catalytic systems, such as the use of strong protic acids H2SO4 [9], HCl [10], various Lewis and Bronsted acids like Bi(NO3)3 [11], Sulfated silica tungstic acid [12], sulfated tungstate [13], SiO2-polyphosphoric acid (SiO2-PPA) [14], silica sulfuric acid [15], bismuth subnitrate [16], cellulose sulfuric acid [17], sulfated polyborate [18], Al2O3-MeSO3H, Al(HSO4)3, Al2O3-SO3H, sulfated zirconia, zeolites, and metal trifles [19] were successfully employed. Further methods involved are ultrasonic [20], microwave-assisted [21] and ionic liquids employing different green catalysts [22].…”

Section: Introductionmentioning

confidence: 99%

In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli

Rajapriyan,

Masood Khan,

Khan R.

et al. 2024

Bull. Chem. Soc. Eth.

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Modern organic synthesis is primarily focused on developing environmentally benign synthetic protocols by employing green chemistry principles. Accordingly, in our recent research work, we herein report the use of modified supramolecular host cyclodextrin as an effective solid based green catalyst for accessing structurally diverse and medicinally relevant pyrimidone architectures. The catalyst and the synthesized compounds 4 (a-r) were characterized using FT-IR, NMR and GC-mass spectroscopy. Major highlights of the reported work include the economical atom process, remarkably gentler reaction conditions, ease of operation, high isolated yields, and excellent catalyst turnover numbers. The molecular docking studies suggest that the compound 4n has hydrogen bonding, hydrophobic and π-pair interactions with the active site of the CXT M 15 receptor. Further, the in-vitro antibacterial study as well as the screening of anti-biofilm activity resulted in a BIC value of 76.79 ± 0.785% at a concentration of 10 µg/mL and morphological alterations induced by DHPMs against the ESBL E. coli strain aggregated with a good result. KEY WORDS: Ethylenediamine modified β-CD, Multicomponent reaction, 3,4-dihydropyrimidin-2(1H)-ones DHPM derivatives, Solvent-free conditions, Reusability, Antibactercidal Bull. Chem. Soc. Ethiop. 2024, 38(4), 1103-1118. DOI: https://dx.doi.org/10.4314/bcse.v38i4.23

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“…[9] Accordingly, SA is recognized as an efficient and economically feasible green catalyst in organic transformations, [10][11][12][13][14] including functional group protections and deprotections, [15] synthesis of isoamyl acetate, [16] polymeric ethers, [17] esterification, [18] acetylation of alcohols and phenols, [19] αamino nitrile formation, [20] tetrahydropyranylation of alcohols, [21] and transesterification of β-ketoesters. [22] Further, other important organic reactions such as Beckmann rearrangement, [23] inter-and intra-molecular imino Diels-Alder reactions, [24] and Pechmann [25] and Biginelli condensations, [26] were successfully realized by the employment of SA of particular importance, owing to its zwitterionic nature and ability to form soluble metal complexes, sulfamic acid is a highly ionized, non-volatile acid, which is safely and eco-friendly used while avoiding the precipitation of undesirable insoluble salts. [27][28][29][30] In spite of the fact that review articles dedicated to SA are already available, the continuous and exponential growth of interest in this unique solid acid calls for frequent updates on the advancements in SA employment in a wide range of industrial, pharmaceutical, chemical, and medicinal applications.…”

Section: Introductionmentioning

confidence: 99%

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

ChemistrySelect

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In recent times, synthetic organic reactions have gained significant attention as they are becoming a versatile tool in the synthesis of pharmaceuticals, agrochemicals and their intermediates. Sulfamic acid (SA) is an acid catalyst that demonstrated high efficiency in various organic transformations that will be highlighted in this review. These include efforts to develop green approaches using SA catalyst for the CÀ C bond formation reactions and functional group trans-formations, as well as the synthesis of various OÀ and Nheterocyclic compounds and other miscellaneous reactions including multicomponent reactions. The easy recovery (for subsequent reuse) of the catalyst by filtration without the need for solvents is an important advantage of SA catalyst. In this review, SA promoted greener methodologies that were developed and the applicability of these methodologies are addressed.

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Efficient Biginelli Reaction Catalyzed by Sulfamic Acid or Silica Sulfuric Acid under Solvent‐Free Conditions

Cited by 33 publications

References 28 publications

Biginelli Reaction: Polymer Supported Catalytic Approaches

Biginelli Reaction: Polymer Supported Catalytic Approaches

In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

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