Open Access Open Access  Restricted Access Subscription Access


Сергей А. Серый, Вадим М. Тимошенко, Юрий Г. Власенко, Эдуард Б. Русанов, Юрий Г. Шермолович
Cover Image


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.

How to Cite
Siryi, S. A.; Timoshenko, V. M.; Vlasenko, Yu. G.; Rusanov, E. B.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2015, 51, 630. [Khim. Geterotsikl. Soedin. 2015, 51, 630.]

For this article in the English edition see DOI 10.1007/s10593-015-1750-1


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

Full Text: PDF (Russian) Supplementary File(s): SUPPLEMENTARY INFORMATION (822KB)



Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia -