title: Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes.
abstract: Copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes were found to be an efficient methodology for the synthesis of ferrocene-labeled steroids. At the same time, a great difference between the reactivity of 2β- or 16β-azido-androstanes and a sterically hindered 6β-azido steroid toward both ferrocenyl-alkynes and simple alkynes, such as phenylacetylene, 1-octyne, propargyl acetate and methyl propiolate, was observed.
authors.affiliation: University of Veszprém, Institute of Chemistry, Department of Organic Chemistry, Egyetem u. 10, P.O. Box 158, H-8200 Veszprém, Hungary.
authors.forename: Klaudia
authors.initials: K
authors.lastname: Fehér
authors.forename: János
authors.initials: J
authors.lastname: Balogh
authors.forename: Zsolt
authors.initials: Z
authors.lastname: Csók
authors.forename: Tamás
authors.initials: T
authors.lastname: Kégl
authors.forename: László
authors.initials: L
authors.lastname: Kollár
authors.forename: Rita
authors.initials: R
authors.lastname: Skoda-Földes
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000731:Androstanes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005296:Ferrous Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000075163:Metallocenes; D013055:Spectrophotometry, Infrared; D013256:Steroids / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D000731:Androstanes; D001386:Azides; D005296:Ferrous Compounds; D000075163:Metallocenes; D013256:Steroids; D003300:Copper; C004998:ferrocene