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PUMMERER REACTIONS OF THIOPYRAN DERIVATIVES AS A METHOD FOR THE PREPARATION OF TRIFLUOROMETHYL-SUBSTITUTED THIOLANES WITH ANTIVIRAL ACTIVITY

С. А. Серый, В. М. Тимошенко, Ю. Г. Власенко, Г. В. Баранова, С. Д. Загородняя, Н. В. Нестерова
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Abstract


2-(p-Tolylsulfanyl)-2-trifluoromethyl-3,6-dihydro-2Н-thiopyran 1-oxides undergo a vinylogous Pummerer reaction upon interaction with trifluoroacetic anhydride, forming 2-(p-tolylsulfanyl)-4-trifluoroacetoxy-2-trifluoromethyl-3,4-dihydro-2Н-thiopyrans. The hydrolysis, acetylation, and free radical desulfanylation of these compounds with a subsequent oxidation of the sulfur atom leads to 4-acetoxy-2‑trifluoromethyl-3,4-dihydro-2Н-thiopyran 1-oxides. The Pummerer addition reaction of the latter with acetic anhydride and boron trifluoride etherate results in a ring contraction and formation of 3-acet-oxy-2-diacetoxymethyl-5-(trifluoromethyl)thiolanes, which could be converted with sodium borohydride to 3-hydroxy-2‑hydroxymethyl-5-(trifluoromethyl)thiolanes having antiviral activity.

How to Cite
Siry, S. A.; Timoshenko, V. M.; Vlasenko, Yu. G.; Baranova, G. V.; Zagorodnya, S. D.; Nesterova, N. V. Chem. Heterocycl. Compd. 2014, 50, 467. [Khim. Geterotsikl. Soedin. 2014, 513.]

For this article in the English edition see DOI 10.1007/s10593-014-1497-0

Keywords


dihydrothiopyran; sulfoxide; thiolane; thiopyran; Pummerer reaction; biological activity

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