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Synthesis 2009(23): 4037-4041  
DOI: 10.1055/s-0029-1217031
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Anita Horvátha,b, Dávid Frigyesc, Sándor Mahób, Zoltán Berented, László Kolláre, 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
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Publikationsverlauf

Received 20 April 2009
Publikationsdatum:
12. Oktober 2009 (online)

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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