Collect. Czech. Chem. Commun. 1997, 62, 1095-1104

Reactions of 21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione with Nitrogen-Containing Nucleophilic Agents

Jiří Protivaa, Thi Thu Huong Nguyena, Jiří Urbanb and Eva Klinotováa

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b J. Heyrovský Institute of Physical Chemistry and Electrochemistry, 182 23 Prague 8, Czech Republic


21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione (1) enters a reaction with acetonitrile catalyzed by perchloric acid, giving unusual products with the furostane skeleton. In contrast to analogous reactions, the reaction with sodium azide results in the azido derivative possessing the non-rearranged ring D. The 1H NMR, 13C NMR, and mass spectra are discussed.

Keywords: Pregnenes; Nitrogen-containing nucleophiles; NMR spectra.