Synthesis of Monosubstituted Trifluoromethylated Derivatives of 2H-thiete, Dihydrothiophenes, and 2H-thiopyrans

Siryi, Serhii A.; Тимошенко, Вадим М.; Rudenko, Tymofii V.; Markitanov, Yuriy M.; Русанов, Эдуард Б.; Shermolovich, Yu. G.

doi:10.1007/s10593-022-03063-0

Cited by 3 publications

(1 citation statement)

References 25 publications

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“…We also previously used this method for generation of thiocarbonyl ylide and found that it readily reacted with polyfluoroalkanethioamides to form new 4-polyfluoroalkyl-1,3-dithiolanes [13]. We also described the cycloaddition of in situ Chloromethyl trimethylsilylmethyl sulfide as precursor to thiocarbonyl ylide generated thiocarbonyl ylide to 3,3,3-trifluoropropene derivatives [14], as well as some its cyclic analogues [15] yielded new 4-(trifluoromethyl)tetrahydrothiophenes with ester, sulfone, sulfoximine, sulfonamide, or phosphonate moiety in the position 3.…”

Section: ■ Introductionmentioning

confidence: 99%

The Synthesis of the Hydrogenated Thiophenes by [3+2] Cycloaddition Reaction of Thiocarbonyl Ylide

Rudenko,

Timoshenko

2023

J. Org. Pharm. Chem.

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Aim. To study the use of chloromethyl trimethylsilylmethyl sulfide as a precursor of thiocarbonyl ylide in [3+2] cycloaddition reaction to a number of α,β-unsaturated compounds and to establish the regularities of the reaction course. To develop an effective method for the synthesis of new dihydro- and tetrahydrothiophene derivatives which are convenient for further modification.Results and discussion. The synthetic approach to tetrahydrothiophenes with substituents in positions 3 and 4 was extended by the [3+2] cycloaddition reaction of thiocarbonyl ylide with a number of compounds containing an activated multiple bond. The stereoselectivity and limitations of this reaction were determined. Further functionalization of the obtained compounds was carried out.Experimental part. Thiocarbonyl ylide was obtained by fluoride ion-promoted 1,3-desilylation of the known chloromethyl trimethylsilylmethyl sulfide. The synthesis of the target compounds involved the [3+2] cycloaddition of such an ylide to a series of compounds with an activated multiple bond. The stereochemistry of the target compounds was determined by 1H NOESY experiments. Synthetic derivatives of thiolancarboxylic acids, in particular aldehydes, alcohols, amines, amidines, were obtained by functionalization of the [3+2] adducts.Conclusions. The synthetic approach to functionalized tetrahydrothiophenes by the [3+2] cycloaddition reaction of thiocarbonyl ylide with a number of compounds containing an activated multiple bond has expanded the limits of application of this reaction and allows obtaining the target compounds in multigram quantities. A high stereoselectivity of this reaction was observed. The reaction products are convenient synthetic precursors to the various classes of organic compounds.

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Section: ■ Introductionmentioning

confidence: 99%

The Synthesis of the Hydrogenated Thiophenes by [3+2] Cycloaddition Reaction of Thiocarbonyl Ylide

Rudenko,

Timoshenko

2023

J. Org. Pharm. Chem.

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Trifluoromethylated 2H‐Thiete, 2,3‐Dihydrothiophenes and 3,4‐Dihydro‐2H‐thiopyranes S,S‐Dioxides in [3+2]‐Cycloaddition Reactions with Diazo Compounds and Nitrilimines

Markitanov,

Siry,

Timoshenko

et al. 2024

ChemistrySelect

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Abstract[3+2]‐Cycloaddition reactions of 3‐trifluoromethyl‐2H‐thiete 1,1‐dioxide, 4(5)‐trifluoromethyl‐2,3‐dihydrothiophene 1,1‐dioxides and 5(6)‐trifluoromethyl‐3,4‐dihydro‐2H‐thiopyrane 1,1‐dioxides with diazomethane proceed with the formation of regioisomeric mixtures of corresponding dihydropyrazole‐fused cycloadducts. Reactions of 3‐trifluoromethyl‐2H‐thiete 1,1‐dioxide with ethyl diazoacetate and in situ generated 2,2,2‐trifluorodiazoethane lead to the regioselective formation of pyrazolino‐sultine derivatives via rearrangement of initially formed pyrazoline‐fused thietane 1,1‐dioxides. Treatment of 3‐trifluoromethyl‐2H‐thiete 1,1‐dioxide and 4‐trifluoromethyl‐2,3‐dihydro‐thiophene 1,1‐dioxide with in situ generated N‐phenyl nitrilimines gives rise to dihydropyrazole‐ thietane 1,1‐dioxides and tetrahydrothiophene 1,1‐dioxides, respectively, in a regioselective fashion.

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3-Cyanothiete 1,1-dioxide: synthesis and cycloaddition reactions

Siryi,

Shishkina,

Timoshenko

2023

Chem Heterocycl Comp

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Synthesis of Monosubstituted Trifluoromethylated Derivatives of 2H-thiete, Dihydrothiophenes, and 2H-thiopyrans

Cited by 3 publications

References 25 publications

The Synthesis of the Hydrogenated Thiophenes by [3+2] Cycloaddition Reaction of Thiocarbonyl Ylide

The Synthesis of the Hydrogenated Thiophenes by [3+2] Cycloaddition Reaction of Thiocarbonyl Ylide

Trifluoromethylated 2H‐Thiete, 2,3‐Dihydrothiophenes and 3,4‐Dihydro‐2H‐thiopyranes S,S‐Dioxides in [3+2]‐Cycloaddition Reactions with Diazo Compounds and Nitrilimines

3-Cyanothiete 1,1-dioxide: synthesis and cycloaddition reactions

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