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


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Article Info

DATE

2015-07

AUTHORS

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

ABSTRACT

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. More... »

PAGES

630-638

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10593-015-1750-1

DOI

http://dx.doi.org/10.1007/s10593-015-1750-1

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1008171654


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