Efficient synthesis of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters

Madabhushi, Sridhar; Kurva, Srinivas; Sriramoju, Vinodkumar; Nanubolu, Jagadeesh Babu; Cirandur, Suresh Reddy

doi:10.1039/c5ra11629e

Cited by 7 publications

(4 citation statements)

References 23 publications

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“…In 2015, Madabhushi's group synthesized two classes of polyfunctionalized thiophenone derivatives using β-oxodithioesters as building blocks (Scheme 3). 12 In this report, β-oxodithioesters 3-1 reacted directly with oxalyl chloride 3-2 producing 4-aroyl-5-(methylthio)thiophene-2,3-diones 3-3 in 96-98% yields under solventand additive-free conditions in a very short time. Furthermore, β-oxodithioesters 3-1 were applied to access 4-aroyl-5-(methylthio)thiophen-3(2H)-ones 3-5 in 61-77% yields with chloroacetic anhydride 3-4, which required adding DMAP as a catalyst.…”

Section: Thiophenesmentioning

confidence: 82%

A decade update on the application of β-oxodithioesters in heterocyclic synthesis

et al. 2023

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Section: Thiophenesmentioning

confidence: 82%

A decade update on the application of β-oxodithioesters in heterocyclic synthesis

et al. 2023

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“…Also, 3-hydroxythiophene-2(3 H )-one (Thyox) are a kind of dihydroxythiophenes and can be produced through dealkylation of 2,3-di- t -butoxythiophen . Although there is no exact report about the environmental consequence of this compound, similar compounds (e.g., thiotetronic acids) bearing carbonyl and hydroxyl functional groups have pharmacological applications . In the case of desulfurization from fuels, these compounds can be easily separated from the organic phase by bringing them in contact with aqueous solvent, owing to their hydrophilic tendency.…”

Section: Resultsmentioning

confidence: 99%

Possibilities and Constraints of the Electrochemical Treatment of Thiophene on Low and High Oxidation Power Electrodes

et al. 2019

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In this research, the electrochemical oxidation of thiophene at platinum and dimensionally stable anode (DSA) electrodes as low oxidation power anodes and at lead/lead oxide (Pb/PbOx) and boron-doped diamond (BDD) electrodes as high oxidation power anodes was comprehensively studied by determining the rate and degree of the electrochemical thiophene oxidation, the Coulombic efficiency (CE), and the selectivity of polar product formation [thiophene-2-one and 3hydroxythiophene-2(3H)-one (Thyox)]. The DSA showed the best performance among the low oxidation power electrodes, with a selectivity of 84.54% toward Thyox formation, a product formation rate of 224.51 mmol/(h m 2 ), a CE of 23.04%, and thiophene conversion of 97.96% in 0.5 M H 2 SO 4 solution for 3 h in ambient temperature. The conversion of thiophene was approximately the same using Pb/PbOx and BDD (about 92%), but Pb/PbOx yielded higher selectivity and product formation rate for Thyox formation [73.68% and 117.72 mmol/(h m 2 ), respectively]. However, CE of BDD (62%) was nearly 3 times greater than that of Pb/PbOx at lower potentials. The experimental results can provide a clear decision in the exploitation of oxidation processes at the industrial scale and could be easily extended to other thiophenic compounds.

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“…Recently, effective methods for the synthesis of 4-acylated-5-substituted thiophene-2,3-diones through acylation of 3-oxo-N-phenyl-3-alkyl/aryl-propanethioamides [14] or methyl 3-oxo-3-arylpropanedithioates [15] by oxalyl chloride at the S atom and the active methylene group have been reported. However, we find the synthesis of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3dione (1) from the addition of ethyl benzoylpyruvate to phenyl isothiocyanate and KOH in DMF with stirring at room temperature [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

Kabirifard

Taghva

Teimouri

et al. 2020

Heteroatom Chemistry

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The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

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Efficient synthesis of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters

Abstract: Efficient methods for the preparation of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters were described.

Cited by 7 publications

References 23 publications

A decade update on the application of β-oxodithioesters in heterocyclic synthesis

A decade update on the application of β-oxodithioesters in heterocyclic synthesis

Possibilities and Constraints of the Electrochemical Treatment of Thiophene on Low and High Oxidation Power Electrodes

Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

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