title: Synthesis of steroid-ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation--copper-catalyzed azide-alkyne cycloaddition reaction sequence.
abstract: Steroids with the 17-iodo-16-ene functionality were converted to ferrocene labeled steroidal 17-carboxamides via a two step reaction sequence. The first step involved the palladium-catalyzed aminocarbonylation of the alkenyl iodides with prop-2-yn-1-amine as the nucleophile in the presence of the Pd(OAc)(2)/PPh(3) catalyst system. In the second step, the product N-(prop-2-ynyl)-carboxamides underwent a facile azide-alkyne cycloaddition with ferrocenyl azides in the presence of CuSO(4)/sodium ascorbate to produce the steroid-ferrocene conjugates. The new compounds were obtained in good yield and were characterized by (1)H and (13)C NMR, IR, MS and elemental analysis.
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: Eszter
authors.initials: E
authors.lastname: Szánti-Pintér
authors.forename: János
authors.initials: J
authors.lastname: Balogh
authors.forename: Zsolt
authors.initials: Z
authors.lastname: Csók
authors.forename: László
authors.initials: L
authors.lastname: Kollár
authors.forename: Agnes
authors.initials: A
authors.lastname: Gömöry
authors.forename: Rita
authors.initials: R
authors.lastname: Skoda-Földes
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D005296:Ferrous Compounds; D013256:Steroids; D010165:Palladium; D003300:Copper