Diacetoxyiodobenzene mediated oxidative dethionation of N-substituted-5-arylmethylidene rhodanines: an efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones

Singh, Sunil P.; Devi, Nepram Sushuma

doi:10.24820/ark.5550190.p009.848

Cited by 6 publications

(2 citation statements)

References 21 publications

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“…Recently, hypervalent iodine compounds such as diacetoxyiodobenzene (DIB) in ethanol at room temperature achieve the conversion of 150 a – k to 151 a – k in high yield, short time, low toxicity, and variety in substituents (Scheme 45). [131] …”

Section: Synthesis Of 24‐thiazolidinedione Ringmentioning

confidence: 99%

“…[130] Recently, hypervalent iodine compounds such as diacetoxyiodobenzene (DIB) in ethanol at room temperature achieve the conversion of 150 a-k to 151 a-k in high yield, short time, low toxicity, and variety in substituents (Scheme 45). [131] On the other hand, rhodanines 152 a-c are oxidized to thiazolidinediones 153 a-c by refluxing in an aqueous solution of chloroacetic acid for 18 hours where chloroacetic acid behaves as an alkylating and oxidizing agent (Scheme 46). [139] Moreover, heating 154 a-b with dimethyl sulfate directly causes alkylation of rhodanines 155 a-b, then the formation of sulfate salt 156 a-b which is hydrolyzed by ethanol to produce thiazolidinediones 157 a-b (Scheme 47).…”

Section: From Rhodaninementioning

confidence: 99%

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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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Section: Synthesis Of 24‐thiazolidinedione Ringmentioning

confidence: 99%

Section: From Rhodaninementioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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A Brief Review on Different Reactions of Rhodanine

Das,

Ray

2024

Journal of Heterocyclic Chem

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ABSTRACT2‐Thioxo‐4‐thiazolidinone which is trivially known as rhodanine is a five‐membered heterocycle, containing a sulfur and nitrogen atom at 1 and 3 positions, respectively. It is a very attractive class of compounds, because derivatization of rhodanine yields a number of molecules having multifarious application in medicinal chemistry and biology. There are many molecules derived from rhodanine which are already being used commercially as drug molecules. So owing to the importance of rhodanine in the field of medicinal chemistry and biology, a comprehensive review familiarizing different derivatives of the parent molecule rhodanine and their syntheses is highly warranted. In this review, we have broadly categorized the reactions of rhodanine as; (a) Knoevenagel condensation through the C‐5 active methylene group with carbonyl compounds, (b) nucleophilic attack on thioxo group at position 2 of rhodanine by aliphatic amines, (c) thioxo to oxo conversion, and (d) all other reactions. So far, to the best of our knowledge, no such literature which accounts for all the different kinds of reactions of rhodanine is reported. Here, we have not only presented the reactions schemes from various literatures, but we have discussed about the advantages and inadequacies of that particular catalytic processes. Moreover, at the end of this article we have given our own critical analysis on these literature reports, based on our understanding and experience.

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Efficient and Chemoselective Procedure for Conversion of Rhodanine Derivatives into 1,3‐Thiazolidine‐2,4‐diones via 1,3‐Dipolar Cycloaddition Reaction and Rearrangement Sequences

et al. 2020

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Herein, we report a chemoselective 1,3‐dipolar cycloaddition reaction between 5‐alkylidene‐ or 5‐arylidene rhodanine derivatives and nitrile oxide generated in situ from dibromoformaldoxime to construct 1,3‐thiazolidine‐2,4‐dione scaffold under mild conditions. This strategy exhibits a distinguished manner to afford thiazolidine derivatives in a simple, rapid and practical route. The results proved that the reaction proceeds through an unpredictable rearrangement and no spirocyclic product is generated. The structures of the target molecules were confirmed by IR, 1H NMR, 13C NMR, mass spectra and unambiguously X‐ray crystal structure analysis.

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Diacetoxyiodobenzene mediated oxidative dethionation of N-substituted-5-arylmethylidene rhodanines: an efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones

Cited by 6 publications

References 21 publications

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

A Brief Review on Different Reactions of Rhodanine

Efficient and Chemoselective Procedure for Conversion of Rhodanine Derivatives into 1,3‐Thiazolidine‐2,4‐diones via 1,3‐Dipolar Cycloaddition Reaction and Rearrangement Sequences

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