Facile Synthesis of Steroidal
Vicinal Hydroxysulfides via the Reaction of Steroidal
Epoxides with Thiols in the Presence of an Ionic Liquid

Anita Horváth; Dávid Frigyes; Sándor Mahó; Zoltán Berente; László Kollár; Rita Skoda-Földes

doi:10.1055/s-0029-1217031

PAPER

Facile Synthesis of Steroidal Vicinal Hydroxysulfides via the Reaction of Steroidal Epoxides with Thiols in the Presence of an Ionic Liquid

Anita Horváth^a,b, Dávid Frigyes^c, Sándor Mahó^b, Zoltán Berente^d, László Kollár^e, Rita Skoda-Földes*^a
^a University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, P.O. Box 158, 8201 Veszprém, Hungary
Fax: +36(88)624469; e-Mail: skodane@almos.uni-pannon.hu;
^b Chemical Works of Gedeon Richter Ltd., P.O. Box 27, 1475 Budapest 10, Hungary
^c Eötvös Loránd University, Institute of Chemistry, Department of Inorganic Chemistry, Pázmány P. sétány 1/A, 1117 Budapest, Hungary
^d University of Pécs, Department of Biochemistry and Medical Chemistry, Szigeti u. 12, 7624 Pécs, Hungary
^e University of Pécs, Department of Inorganic Chemistry, P.O. Box 266, 7624 Pécs, Hungary

Abstract

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Abstract

Ring-opening of steroidal 2,3-epoxides with thiols can be carried out effectively in the Brønsted acidic ionic liquid [Hmim]⁺[BF₄]^- as a recyclable solvent and catalyst. The use of other ionic liquids/molten salts resulted in a decrease in the conversion and/or in reduced selectivity. In [bmim]⁺Br^-, a conversion of 2,3-epoxy-17-ones into 2,17- and 3,17-diones was also observed.

Key words

catalysis - epoxides - ionic liquids - ring-opening - steroids - thiols

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