Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies

Thangaraj, Muthu; Ranjan, Bibhuti; Ramesh, Muthusamy; Murugesan, Arul; Gengan, Robert Moonsamy

doi:10.1002/jhet.3465

Cited by 8 publications

(4 citation statements)

References 75 publications

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“…[46][47][48][49][50] Such a widespread medicinal and biological profile makes them interesting candidates for medicinal chemists. Thangaraj et al [51] developed a green and sustainable method for the synthesis of a library of functionalized substituted pyrans 42, 43, 43 a, 44, 46 from the reaction of the aldehyde 1, malononitrile 39 and different cyclic and acyclic active methylene compounds thiazolidine-2,4-dione/2-thioxothiazolidin-4-one 40, dimedone 41, ethylacetoacetate 36, barbituric acid 45 respectively in presence of HASIL (humic acid supported 1-butyl-3-methyl imidazolium thiocyanate) catalyst (Scheme 12). Some interesting observations worth mentioning here is the superiority of the HASIL catalyst over humic acid.…”

Section: Humic Acid In Functionalized Pyran Synthesismentioning

confidence: 99%

Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

Swaraj Acharya,

Bhusan Parida

2024

ChemistrySelect

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The growing pollution and threat to the environment demand green synthetic methods. Green chemistry mainly focuses on minimizing the waste and utilization of green solvents, energy sources, and catalysts and prefers one‐pot reactions. In this context, humic acid (HA), a natural bioorganic catalyst found in rivers, peat coal and sewage; is a high molecular weight macromolecule containing multifunctional groups, mainly contains quinone, phenolic OH, and COOH groups which make it acidic and activate carbonyl groups by protonation. Owing to its green aspect such as biodegradability, recyclability and reusability, humic acid is considered as sustainable bioorganic catalyst which meets the criteria for industrial requirements. The HA is mild acidic in nature, thus many functional groups tolerate in the HA catalyzed reactions. After few initial reports in 2001 and 2009, the HA catalyzed reactions gained much attention by the organic synthetic community from 2019 in aldol condensation, Knoevenagel condensation, Claisen‐Schmidt reaction, Michael addition, Strecker synthesis, tetrazole synthesis, Hantzsch dihydropyridine synthesis, hydrosilylation of terminal alkenes, hydrogenation, α‐aminophosphonate synthesis, cross coupling reactions such as Heck and Suzuki coupling reactions. Herein we report the comprehensive analysis on the role of HA in organic transformations providing diverse array of molecular scaffolds till date and future perspective.

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Section: Humic Acid In Functionalized Pyran Synthesismentioning

confidence: 99%

Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

Swaraj Acharya,

Bhusan Parida

2024

ChemistrySelect

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“…Also, researchers have developed a three‐component tandem reaction in aqueous medium using humic acid‐supported ionic liquid catalyst (HASIL) to afford the same result 322 a – b (Scheme 114). [367] …”

Section: Reactivity Of 24‐thiazolidinedionementioning

confidence: 99%

“…[366] Also, researchers have developed a three-component tandem reaction in aqueous medium using humic acidsupported ionic liquid catalyst (HASIL) to afford the same result 322 a-b (Scheme 114). [367] The same idea is modulated to yield 4,7dihydrothiazolo [4,5-b]pyridin-2(3H)-one compounds by aza Diels-Alder method. This method is done either by adding ammonium acetate to the tandem reaction or using cyclic enamine instead of malononitrile.…”

Section: Formation Of Fused Heterocyclesmentioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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“…Some biologically active tetrahydrobenzo [b]pyrans Due to the importance of these category of heterocycles, many research groups have tried to synthesize them using various catalytic methods. The synthesis of these compounds has been studied by employing catalysts such as L-ascorbic acid, 12 water extract of muskmelon fruit shell ash (WEMFSA), 13 cinchonine, 14 humic acid supported ionic liquid, 15 sodium malonate, 16 sodium citrate, 17 N,Ndimethylbenzylamine (DMBA), 18 potassium phthalimide, 19 potassium hydrogen phthalate, 20 1-ethyl-3methylimidazolium 2-hydroxybenzoate, 21 L-pyrrolidine-2-carboxylic acid sulfate, 22 1,3dihexylimidazolium 2-aminobenzoate, 23 choline taurinate, 24 artificial sweetener ionic liquid, 25 triethanolamine, 26 1-methyl-3-(2-phenoxyethyl)-1H-imidazol-3-ium hydroxide, 27 choline chloridepentaerythritol, 28 1-ethyl-3-methylimidazolium acetate, 29 bovine serum albumin and NaCl (ball milling method), 30 lipase from Thermomyces lanuginosus immobilized on particle silica gel (TLIM), 31 trishydroxymethylaminomethane, 32 ammonium carbonate, 33 MgSO4, 34 K2CO3/montmorillonite, 35 and free-ZnO nanoparticles. 36 Electrolysis using LiClO4 37 or deep eutectic solvent, 38 catalyst-free using UV365 light, 39 magnetized water, 40 aqueous ethylene glycol at 100 °C41 as well as aqueous PEG-400 42 are among approaches for the synthesis of tetrahydrobenzo [b]pyrans.…”

mentioning

confidence: 99%

Three-Component Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by Sodium Cyclamate

Kiyani¹,

Baghaie²

2022

HETEROCYCLES

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The one-pot three-component cyclocondensation for the synthesis of tetrahydrobenzo [b]pyran derivatives in the presence of sodium cyclamate has been investigated. The three-component reaction was carried out in water medium under refluxing condition. Screening the reaction conditions revealed that 20 mol% sodium cyclamate refluxing water afforded the best results. Under green conditions, different substituted tetrahydrobenzo[b]pyrans were obtained from simple available starting materials, including malononitrile, functionalized benzaldehydes, and dimedone, via using an established efficient and straightforward approach.Multicomponent reactions (MCRs) involve at least three reactants that reacted in one-pot approach to synthesize valuable organic compounds and pharmacologically active molecules with high complexity and diversity as well as minimum side reactions. Green bond-forming, atomic and structural economy, step economy, high bond-forming index, avoidance of complicated purification processes and separation of intermediates, time-saving, mild conditions, environmental friendliness, elimination of waste production, energy-saving, and excellent functional group compatibility are the merits of MCRs. 1 In this reason, MCRs have been used for the synthesis of various heterocyclic compounds. 2 Tetrahydrobenzo[b]pyran derivatives are one of the biologically scaffolds owing to their applications in the synthetic and medicinal chemistry. 3 These important oxygen-containing heterocyclic compounds exhibit bioactivities, including anti-coagulant, 3 anti-anaphylactic, 3 calcium antagonist, 3 anticancer, 4 antibacterial, 5 anti-inflammatory, 6 lactamase inhibitor, 7 antifungal, 8 antioxidant, 8 anti-Huntington, anti-Alzheimer, anti-Schizophrenia, and anti-Parkinson. 3,9 The structures of some biologically active tetrahydrobenzo [b]pyrans are depicted in Figure 1. Besides, tetrahydrobenzo[b]pyrans were applied as starting materials to synthesize spirocyclopropylbarbiturates, 10 spirocyclopropylpyrazolones,

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Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies

Cited by 8 publications

References 75 publications

Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

Three-Component Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by Sodium Cyclamate

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