Selective Synthesis of Ortho-Substituted 2-Aryl-3-phenyl-1,3-thiazolidin-4-one Sulfoxides and Sulfones by S-Oxidation with Oxone®

Cannon, Kevin C.; Alkurdi, Alaa; Himel, Humayra; Kurochka, Iryna; Liu, Sabrina; Costa, Miguel; Sundberg, Brynn N.; Lagalante, Anthony F.

doi:10.5539/ijc.v9n4p87

Cited by 2 publications

(2 citation statements)

References 23 publications

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“…from 1,3‐thiazolidin‐4‐ones 514 in the presence of oxone/MeOH (Scheme 159). [371] The reason for making these systems was because of the biological applicability for example against cancer cells in addition to their wide range of organic applications as well.Moreover, in another study, the same group has also reported a selective synthesis of ortho ‐substituted 2‐aryl‐3‐phenyl‐1,3‐thiazolidin‐4‐one sulfoxides 518 and sulfones 519 in 33–99 % yields from 2‐aryl‐3‐phenyl‐1,3‐thiazolidin‐4‐ones 517 viaS ‐oxidation by virtue of oxone‐mediated transformation as detailed in the Scheme 160 [372] …”

Section: Oxidation Of Diverse Functional Groupsmentioning

confidence: 99%

“…[371] The reason for making these systems was because of the biological applicability for example against cancer cells in addition to their wide range of organic applications as well.Moreover, in another study, the same group has also reported a selective synthesis of orthosubstituted 2-aryl-3-phenyl-1,3-thiazolidin-4-one sulfoxides 518 and sulfones 519 in 33-99 % yields from 2-aryl-3-phenyl-1,3thiazolidin-4-ones 517viaS-oxidation by virtue of oxone-mediated transformation as detailed in the Scheme 160. [372] Generally, sulfoxides and sulfones are the vital class of compounds as they exhibit wide applications in organic synthesis, biology, agrochemicals, pharmaceuticals, and polymer chemistry. They also serve as valuable synthons in CÀ C bond formation, Diels-Alder reaction, as chiral auxiliaries, and in medicinal chemistry as antiulcer, cardiotonic agents, antihypertensive, CNS-stimulants besides vasodilators.…”

Section: Oxone-mediated Oxidation Reactions Of Diverse Organic Systemsmentioning

confidence: 99%

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Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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Section: Oxidation Of Diverse Functional Groupsmentioning

confidence: 99%

Section: Oxone-mediated Oxidation Reactions Of Diverse Organic Systemsmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Solvent-free MALI-MGRE Procedure for Synthesizing 1,4-thiazolidin-4- one MALI (Mercaptoacetic Acid Looking Imine) MGRE (Mechanical Grinding Reaction Equipment)

Santos¹,

Jones²,

Silva³

2023

COS

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Background: 1,3-Thiazolidin-4-ones are heterocycles whose importance in the pharmaceutical market has already been established. Many of these synthetic derivatives, which contain a thiazolidinone nucleus, are currently used in various commercial formulations or are already in clinical trials for the treatment of disease for their anticonvulsant, antihypertensive and antidiabetic activities in addition to their activity against Streptomyces. 1,3-Thiazolidin-4-ones are produced mainly by cyclocondensation between an imine (generated in situ by the reaction of an aldehyde with an amine) and α-mercaptoacetic acid, known as the MALI (Mercaptoacetic Acid Looking Imine) reaction. Objective: A solvent-free methodology was developed to synthesize a 1,3-thiazolidin-4-one family by the MALI reaction. An apparatus was developed to grind a solid-liquid mixture of anilines, benzaldehydes and thioglycolic acid to activate the reaction. This apparatus was named MGRE (mechanical grinding reaction equipment). Methods: Substituted aniline 2 (4 mmol), substituted benzaldehyde 1 (4 mmol) and thioglycolic acid 3 (12 mmol) were placed in a mortar. The reagents were macerated using the MGRE at room temperature for a specified time period (see Table 1). At the end of the reaction, the product was poured into ice, the precipitate formed was neutralized (with 5% NaHCO3), and the solution was extracted in ethyl acetate and dried in MgSO4. The solid was recrystallized from MeOH/H2O. Results: The developed MGRE is a modification of a rod used in a mechanical stirrer. This adaptation is inexpensive and simple in construction, and it enables reactions to occur over long periods of time that would be exhaustive for manual grinding. Fifteen (1,3) thiazolidin-4-ones were produced. The products were synthesized using the solvent-free MALI-MGRE procedure. Conclusions: The MALI-MGRE methodology developed to produce 1,3-thiazolidin-4-ones showed a good reaction scope, has an easy work-up and is solvent-free. Consequently, MALI-MGRE is classified as a green methodology. An innovation of this study is the construction of the MGRE, which involves modifying the rod in a mechanical stirrer. The equipment is easy and inexpensive to construct and may be useful for various reactions involving grinding.

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Selective Synthesis of Ortho-Substituted 2-Aryl-3-phenyl-1,3-thiazolidin-4-one Sulfoxides and Sulfones by S-Oxidation with Oxone®

Cited by 2 publications

References 23 publications

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Solvent-free MALI-MGRE Procedure for Synthesizing 1,4-thiazolidin-4- one MALI (Mercaptoacetic Acid Looking Imine) MGRE (Mechanical Grinding Reaction Equipment)

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