Alum catalyzed simple and efficient synthesis of 5-arylidene-2,4-thiazolidinedione in aqueous media

Shelke, Kiran F.; Sapkal, Suryakant B.; Kakade, Gopal K.; Sadaphal, Sandip A.; Shingate, Bapurao B.; Shingare, Murlidhar S.

doi:10.1080/17518250903478345

Cited by 43 publications

(23 citation statements)

References 30 publications

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“…The reaction performance was also described in the medium of the aldehyde or ketone (without solvent addition) [21], polyethyleneglycol-300 [47] or based on the green chemistry approach. Moreover, performance of such condensation in aqueous solutions [48]; usage of atypical agents as well as ionic liquids [49]; the soluble polymer-supported synthesis [50] have also been investigated. Microwave assistant organic synthesis approach was also successfully employed [51,52].…”

Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Modification Of the C5 Position Of The Thiazolidinone Corementioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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“…Various methods were reported for the synthesis of 5-arylidine-2,4-thiazolidinediones using piperidine in ethanol, 10 piperidine and benzoic acid in toluene, 11 piperidine benzoate in toluene, 12 potassium carbonate in DMF 13 and sodium acetate in acetic acid. 14 Various alternative methods are also reported for the synthesis of 5-arylidine-2,4-thiazolidinediones using microwave irradiation of the substrates/reactants supported on KF/Al 2 O 3 , 15 alum 16 and in PEG-300. 17 The reported methods have one or other kind of drawbacks like the use of toxic, hazardous, flammable organic solvents, expensive catalysts, prolonged reaction time and heating.…”

Section: Introductionmentioning

confidence: 97%

Dicationic Ionic Liquid Mediated Synthesis of 5‐Arylidine‐2,4‐thiazolidinediones

et al. 2011

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“…Several bases such as piperidine, [17] piperidinium acetate, [18] sodium acetate [19] and ammonium acetate [20] were utilized to accelerate the Knoevenagel condensation. The catalytic function of urea and thiourea, [16] benzoic acid, [21] polyethylene glycol-300, [22] potash alum, [23] L-proline, [23] boric acid, [23] oxalic acid, [23] ionic liquids, [24] Bakers yeast, [25] Mg-doped Ce-Zr [26] and morpholine [27] were utilized in the improved syntheses.…”

Section: Introductionmentioning

confidence: 99%

Tetrabutylammonium bromide and K₂CO₃: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation

Kumar

Swathi²,

Navatha³

et al. 2014

Journal of Sulfur Chemistry

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Phase-transfer catalyzed, energy-efficient and facile synthesis of 5-arylidene-1,3-thiazolidine-2,4-diones was developed. Three independent variables (temperature, bases and phase-transfer catalyst (PTC)) were screened through one-factor-at-a time (OFAT) study. The optimum reaction conditions suggested by the OFAT analysis were the use of tetrabutylammonium bromide (8 mol%) and potassium carbonate (1 mmol) for the reaction at 100°C. The nitrogen of PTC stabilizes carbonyl groups of thiazolidine-2,4-dione (TZD). The active methylene hydrogen of TZD forms potassium salt with potassium carbonate and generates 5-arylidene-1,3-thiazolidine-2,4-diones (1-16) through nucleophilic attack on the carbonyl carbon of arylaldehydes. The prominent advantages of this new process are economic viability, shorter reaction time (15 min), simple product isolation (non-chromatographic method), good to excellent yields (78-96%) and solvent-free conditions.

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Alum catalyzed simple and efficient synthesis of 5-arylidene-2,4-thiazolidinedione in aqueous media

Cited by 43 publications

References 30 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Dicationic Ionic Liquid Mediated Synthesis of 5‐Arylidine‐2,4‐thiazolidinediones

Tetrabutylammonium bromide and K₂CO₃: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation

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Alum catalyzed simple and efficient synthesis of 5-arylidene-2,4-thiazolidinedione in aqueous media

Cited by 43 publications

References 30 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Dicationic Ionic Liquid Mediated Synthesis of 5‐Arylidine‐2,4‐thiazolidinediones

Tetrabutylammonium bromide and K2CO3: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation

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Tetrabutylammonium bromide and K₂CO₃: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation