Pummerer Reactions of Thiopyran Derivatives as a Method for the Preparation of Trifluoro-Methyl-Substituted Thiolanes with Antiviral Activity

Siry, S. A.; Тимошенко, Вадим М.; Vlasenko, Yu. G.; Баранова, Г. В.; Zagorodnya, Svіtlana; Nesterova, N. V.

doi:10.1007/s10593-014-1497-0

Cited by 9 publications

(6 citation statements)

References 31 publications

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“…corresponds to structure 6a . Similar stereoselectivity of the desulfanylation of dihydrothiopyran derivatives has already been observed , …”

Section: Resultssupporting

confidence: 79%

“…For the construction of functionalized thiopyran ring we applied thia‐Diels–Alder methodology consisting in the cycloaddition between fluorinated dithiocarboxylates and protected 1‐hydroxydienes. Fluorinated dithioesters can be readily prepared by the thioacylation of thiols with polyfluorothioacyl chlorides and their reactions with symmetrical dienes produce high yields of cycloadducts in mild conditions , . Little is known about [4+2]‐cycloadition between fluorinated dithiocarboxylates and unsymmetrical dienes.…”

Section: Resultsmentioning

confidence: 99%

“…With the aim to extend the scope of this reaction and as a part of our ongoing work on the chemistry of fluorinated thiopyran derivatives, we focused on the polyfluoroalkylated thiopyranoid glycal analogs (Figure , X = S, R 2 = R F ). Besides being synthetically challenging structures of academic interest, they seem potent substrates for Ferrier (I) reaction.…”

Section: Introductionmentioning

confidence: 99%

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Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

et al. 2018

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The synthesis of a single diastereomer of 3‐acetoxy‐2‐(trifluoromethyl)‐4‐hydroxy‐3,4‐dihydro‐2H‐thiopyran from the mixture of diastereomeric cycloadducts of p‐tolyl trifluorodithioacetate and 1‐acetoxybutadiene is described. Its acetylation and nucleophilic chlorination provides glycosylating agents with different leaving groups have been prepared. Their reactions with various O‐, S‐, N‐ and C‐nucleophiles have been studied. Depending on the conditions of the experiments, the reactions proceed as Ferrier (I) reactions affording 3‐acetoxy‐2‐(trifluoromethyl)‐6‐substituted‐3,6‐dihydro‐2H‐thiopyrans or as formal direct replacement of the leaving group in the position 4 giving 3‐acetoxy‐2‐(trifluoromethyl)‐4‐substituted‐3,4‐dihydro‐2H‐thiopyrans. The stereochemistry of the resulting products and all their precursors is discussed.

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“…corresponds to structure 6a . Similar stereoselectivity of the desulfanylation of dihydrothiopyran derivatives has already been observed , …”

Section: Resultssupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

et al. 2018

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“…The latter compound was prepared by the [4+2]-cycloaddition of the corresponding dithiocarboxylate with a suitable 1,3-diene. Taking into account the high total yield of isolated products, this ring contraction may be considered as a method of choice for the preparation of 2-trifluoromethyl thiolanes 21 ( Scheme 10 ) [ 32 ].…”

Section: Five-membered S-heterocyclesmentioning

confidence: 99%

“…Over the past two decades, the factors affecting the reactions of polyfluoroalkane thiocarboxylic acid esters with 1,3-dienes of various structures have been studied in detail and diverse synthetic applications of the obtained derivatives of dihydrothiopyrans have been considered [ 32 , 68 , 69 , 70 ]. As a result of these reactions, at least one new stereogenic center was generated by the Diels–Alder addition.…”

Section: Six-membered S-heterocyclesmentioning

confidence: 99%

Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions

2022

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Fluorinated heterocycles constitute an important group of organic compounds with a rapidly growing number of applications in such areas as medicinal chemistry, agrochemicals production, polymer chemistry, as well as chemistry of advanced materials. In the latter case, fluorinated thiophenes are considered as a lead class of compounds with numerous spectacular applications. On the other hand, cycloaddition reactions offer a superior methodology for stereo-chemically controlled synthesis of heterocycles with a diverse ring size and a variable number of heteroatoms. A comprehensive review of methods based on cycloaddition reactions and applied for construction of fluorinated and/or fluoroalkylated S-heterocycles has not yet been published. For this reason, the main goal of the presented review was to fill the existing gap and to summarize the results published over last six decades. In this context, the [3+2]- and [4+2]-cycloadditions (Huisgen reactions, and Diels–Alder reactions, respectively) are of special importance. Some questions related to the discussed mechanisms of cycloaddition processes observed in reactions with electron deficient, fluorinated substrates (dipolarophiles and dienophiles), and electron-rich sulfur containing counter partners, are of fundamental importance for the development of interpretations of organic reaction mechanisms.

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The synthesis and properties of 6-trifluoromethyl-substituted thiopyrano[3,4-d]isoxazole derivatives

Siryi

Тимошенко

Vlasenko

et al. 2015

Chem Heterocycl Comp

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Pummerer Reactions of Thiopyran Derivatives as a Method for the Preparation of Trifluoro-Methyl-Substituted Thiolanes with Antiviral Activity

Cited by 9 publications

References 31 publications

Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

Trifluoromethylated Thiopyranoid Glycals: Synthesis and Ferrier (I) Type Reactions

Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions

The synthesis and properties of 6-trifluoromethyl-substituted thiopyrano[3,4-d]isoxazole derivatives

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