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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 7, pp 630–638 | Cite as

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

  • Serhii A. Siryi
  • Vadim M. Timoshenko
  • Yurii G. Vlasenko
  • Eduard B. Rusanov
  • Yuriy G. Shermolovich
Article

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.

Keywords

isoxazole isoxazoline nitrile oxide thiopyran thiopyrano[3,4-d]isoxazole cleavage [3+2] cycloaddition Pummerer reaction reduction 

Supplementary material

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ESM 1 (PDF 822 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Serhii A. Siryi
    • 1
  • Vadim M. Timoshenko
    • 1
  • Yurii G. Vlasenko
    • 1
  • Eduard B. Rusanov
    • 1
  • Yuriy G. Shermolovich
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine

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