Catalytic Applications of Saccharin and its Derivatives in Organic Synthesis

Banerjee, Bubun; Bhardwaj, Vaishali; Kaur, Amninder; Kaur, Gurpreet; Singh, R. Arvind

doi:10.2174/1385272823666191121144758

Cited by 35 publications

(5 citation statements)

References 94 publications

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“…MCR has several advantages such as effective simplicity, eco-friendly, synthetic convergence, atom economy, bond efficiency, least waste disposal, least synthetic period and modest purification steps. [2] Moreover, it supports the synthesis of diversely complicated molecules from simple commercially available materials in a one-pot strategy without purification.…”

Section: Introductionmentioning

confidence: 91%

“…This facilitates the conversion of the final product from the intermediate. [2][3][4][5][6] Recently, PDCA has been used as an organocatalyst in many organic syntheses, because it is relatively stable, easy to handle, insensitive to small amounts of air and moisture, solubility in water, lower toxicity, non-metallic nature, costeffectiveness, readily available and, a weak protic acid having acidic hydrogen's with pK 1 = 2.16 and pK 2 = 4.76. Also, it is explored as a bifunctional organocatalyst for hydro phosphorylation of carbonyls.…”

Section: Introductionmentioning

confidence: 99%

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2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

Govindhan¹,

Nagarajan²

2021

ChemistrySelect

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An efficient and simple method for the synthesis of various amidoalkyl-2-naphthols, dihydropyrimidin-2(1H)-ones (DHPM) and bis-indoles has been developed using 2,6-pyridine dicarboxylic acid (PDCA), as an organocatalyst. All the reactions were performed through a one-pot multicomponent strategy. Reactants of the corresponding reaction were mixed in a single pot along with PDCA catalyst and suitable temperature and duration, yielded the corresponding products in moderate to excellent yield. The proposed method offers various advantages like shorter reaction time, operational simplicity, metalfree, readily accessible catalyst, no column chromatographic method, a cost-effective and acceptance of a wide range of substrates and good yields.

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Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

Govindhan¹,

Nagarajan²

2021

ChemistrySelect

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“…Moreover, they were proved to be a useful ingredient in the electroplating industry [ 7 , 8 , 9 , 10 , 11 ]. In addition, saccharin and its derivatives were used as catalysts and agents in organic reactions, for example N -bromosaccharin is employed as a catalyst, brominating agent, and oxidizing agent in various organic reactions [ 12 ]. On the other hand, saccharin and its derivatives have a broad spectrum of biological and pharmaceutical activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer, Antioxidant, Anti-Inflammatory, Antimicrobial Activities, Molecular Docking, and DFT Studies of Sultams Derived from Saccharin

et al. 2022

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A series of N-substituted saccharins namely 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl) acetonitrile (2) and (alkyl 1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl) acetate (3a–g) were synthesized, in moderate to excellent yields, from commercially available starting materials by two different approaches and their chemical structures were characterized by spectroscopic techniques (1H-NMR, 13C-NMR, IR, and MS). All the synthesized compounds were evaluated for their anti-inflammatory toward IL-6 and TNF-α, antioxidant, as well as their anticancer activities against hepatic cancer cells. In addition, their anti-fungal and antibacterial activities against both Gram-positive and Gram-negative bacteria were tested. All the tested compounds have exhibited excellent (3a, d, e) to moderate anti-inflammatory activity. Additionally, esters (3b, f) and nitrile (2) showed excellent antioxidant activity. Furthermore, ester 3f, with isopropyl ester, exhibited the highest cytotoxic activity compared to the other esters. Moreover, all compounds were evaluated as selective inhibitors of the human COX-1 enzyme using molecular docking by calculating the free energy of binding, inhibition constant, and other parameters to find out the binding affinity. The molecular study showed that esters (3d, f) and nitrile (2) revealed the highest binding affinities, hence enhancing the inhibition activity with the active site of the COX-1 enzyme. All the tested compounds have more negative Gibbs free, electrostatic, and total intermolecular energies than the standard inhibitor ASA. These results indicate that, all the tested sultams are potent anti-inflammatory drugs as compared to standard inhibitors. Finally, the chemical properties and the quantum factors of synthesized sultams were calculated based on density functional theory (DFT) to predict reactivity, and then correlated with the experimental data. Ester 3f showed the lowest ionization potential and lowest energy gap (Egap = 7.5691 eV), which was correlated with its cytotoxic activity. Furthermore, the spatial electron distribution of HOMO, LUMO were computed and it clearly indicates the electron donation ability of all the tested compounds.

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“…Under these environmentally conscious days, metal-free organocatalysts have gained significant attention due to their environmental friendliness. [36][37][38][39][40][41][42][43][44][45] Recently, our research group has explored the catalytic efficacies of mandelic acid for various organic transformations. [46][47][48][49][50] In this communication we wish to report another simple and efficient mandelic acid catalyzed protocol for the synthesis of a series of structurally diverse tri-substituted methane derivatives viz., 5,5'-(arylmethylene)bis(6-amino-pyrimidine-2,4(1H,3H)diones) and 2,2'-(arylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enones) in aqueous ethanol at room temperature (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Mandelic acid catalyzed one-pot pseudo three-component synthesis of various trisubstituted methane derivatives at room temperature

Banerjee¹,

Singh²,

Sharma³

et al. 2022

Arkivoc

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A simple, mild, eco-friendly, general and convenient approach has been developed for the synthesis of various trisubstituted methane derivatives via one-pot pseudo three-component reactions between one equivalent of aromatic aldehydes and two equivalents of 6-amino-uracils or dimedone respectively using a catalytic amount of mandelic acid as a low cost, commercially available, efficient organo-catalyst in aqueous ethanol at room temperature.

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Catalytic Applications of Saccharin and its Derivatives in Organic Synthesis

Cited by 35 publications

References 94 publications

2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

Synthesis, Anticancer, Antioxidant, Anti-Inflammatory, Antimicrobial Activities, Molecular Docking, and DFT Studies of Sultams Derived from Saccharin

Mandelic acid catalyzed one-pot pseudo three-component synthesis of various trisubstituted methane derivatives at room temperature

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