Oxidation of thiourea and substituted thioureas: a review

Sahu, Sandhyamayee; Sahoo, Prangya Rani; Patel, Sabita; Mishra, Bijay K.

doi:10.1080/17415993.2010.550294

Cited by 94 publications

(45 citation statements)

References 110 publications

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“…We proposed the mechanism in light of the oxidation by oxochromium VI compounds, the oxidation of thioureas and the evolution of SO 2 (Scheme ). Other factors were considered; (a) the rapid evolution of SO 2 gas which indicated that the oxidation of sulfur was an earlier step; (b) absence of any traces of elemental sulfur which revealed that oxidation of sulfur has occurred while it was linked to some intermediate; therefore, we ignored that sulfur was separated, in the elemental form, then has oxidized; (c) sulfur functions are capable to behave free radical reactions; and (d) the transition metal ions induce free radical reactions . Thus, it was proposed that the reaction started by the attack of the lone pair of electrons, in the CS, at the chromium ions; the originated chromate anion, in turn, attacked the electron deficient sulfur affording the intermediate [ VI ].…”

Section: Resultsmentioning

confidence: 99%

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Saied

Abdelwahab

Hashem

et al. 2020

Journal of Heterocyclic Chem

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1‐Aryl, 1,3‐diaryl‐ and 5‐(2‐oxo‐2‐arylethyl)‐2‐thioxo‐imidazolidin‐4‐ones 2 were prepared as before, nevertheless, equivalent amounts of potassium hydroxide were added to the reaction conditions. This change, dramatically, reduced the reaction time and highly increased the yield of some derivatives. Treatment of 2 with sulfuric acid converted them into their analogous (E)/(E,Z)‐5‐(2‐oxo‐2‐arylethylidene) derivatives 3. Reactions of 2 and/or 3 with chromium trioxide affected their conversion into the corresponding 2,4‐diones 4 and 5, respectively. Treatment of 2 and/or 3 with ethyl bromoacetate affected conversion of the former into their respective 2,4‐diones 4, whereas it gave the respective 2‐alkylthio derivatives of the latter. Reactions of 2b with aromatic aldehydes gave mixtures of spiro‐1H‐ and 2H‐pyrrole diastereomers. Structures of the new products were evidenced by infrared, EI‐MS, 1H‐ and 13C‐NMR spectroscopic measurements. Many of the selected compounds showed good antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Saied

Abdelwahab

Hashem

et al. 2020

Journal of Heterocyclic Chem

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“…Figure a shows the 13 C NMR spectrum of Tu ( 13 C‐enriched), and Fig. b shows that of the oxidation reaction of Tu by H 2 O 2 , which resulted in the formation of urea, Tu dioxide, and (NH 2 ) 2 CO 2 S . When 0.25 equiv enriched Tu was added to 1 equiv [Au( cis ‐DACH)Cl 2 ]Cl, the color of the solution changed to yellow (Fig.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic and Electrochemical Studies of the Interaction of Some Gold(III) Complexes with Biologically Relevant Thiones

Sulaiman

Omer

Kawde

et al. 2018

Int J of Chemical Kinetics

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The interaction of gold(III) complexes, [Au(cis‐DACH)Cl2]Cl and [Au(cis‐DACH)2]Cl3 complexes (DACH = cis‐1,2‐diaminocyclohexane), with 13C, 15N‐enriched thiourea (Tu) and 1,3‐diazinane‐2‐thione ligands was investigated. The progress of these reactions was monitored by NMR (1H, 13C, and 15N) and UV–vis spectroscopy as well as square wave stripping voltammetry. The kinetic studies of the substitution reactions between the above‐mentioned complexes with thiones in aqueous solutions containing 30 mM KCl, which is used to suppress the hydrolysis of the chloride complexes, were conducted. These reactions were followed under pseudo–first‐order conditions as functions of ligand concentration, pH, and temperature. The activation parameters (ΔH#, ΔS#) were calculated from Eyring plots, and the negative values of ΔS≠ lend support for an associative mechanism. The kinetic data also indicated a relatively higher reactivity of [Au(cis‐DACH)Cl2]Cl than that of [Au(cis‐DACH)2]Cl3 toward the thiones.

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“…Among the solvents tested, acetonitrile gave the best yield of disulfide 2a (entries [8][9][10]. More importantly, the yield of the desired product 2a was significantly decreased when GO was replaced with other carbon promoters such as natural flake graphite, hydrazine-reduced graphene oxide and activated carbon under the same condition (entries 11-13).…”

Section: Accepted Manuscriptmentioning

confidence: 97%

Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent

Khalili

2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Oxidation of thiourea and substituted thioureas: a review

Cited by 94 publications

References 110 publications

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Spectroscopic and Electrochemical Studies of the Interaction of Some Gold(III) Complexes with Biologically Relevant Thiones

Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent

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