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

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Chemistry of Heterocyclic Compounds Aims and scope

The first representatives of the novel 4,7а-dihydro-3аН-thiopyrano[3,4-d]isoxazole heterocyclic system, containing an ester, carboxyl, or hydroxymethyl group at position 3 and a trifluoromethyl group at position 6 were obtained by [3+2] cycloaddition reaction of ethyl cyanocarboxylate N-oxide and 6-trifluoromethyl-2Н-thiopyran, followed by further transformations of the ethyl 6-trifluoromethyl-4,7а-dihydro-3аН-thiopyrano[3,4-d]isoxazole-3-carboxylate intermediate. The cleavage of the isoxazoline ring of the obtained compounds led to the formation of 6-trifluoromethyl-2Н-thiopyran derivatives with nitrile or carbonyl-containing functionality at position 3. Transformations of the thiopyran moiety in 4,7а-dihydro-3аН-thiopyrano[3,4-d]isoxazole were studied for the case of Pummerer reaction product with oxidized sulfur atom, ethyl 6-trifluoromethyl-4,7а-dihydro-3аН-thiopyrano[3,4-d]isoxazole-3-carboxylate 5-oxide, which was converted to ethyl 6-trifluoromethyl-4Н-thiopyrano[3,4-d]isoxazole-3-carboxylate.

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Correspondence to Yuriy G. Shermolovich.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(7), 630–638

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The Supplementary Information file containing 1H, 13C NMR spectra and selected X-ray data of the synthesized compounds is available for authorized users.

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Siryi, S.A., Timoshenko, V.M., Vlasenko, Y.G. et al. The synthesis and properties of 6-trifluoromethyl-substituted thiopyrano[3,4-d]isoxazole derivatives. Chem Heterocycl Comp 51, 630–638 (2015). https://doi.org/10.1007/s10593-015-1750-1

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