title: A systematic approach to the synthesis of androstane-based 3,17-dicarboxamides (homo- and mixed dicarboxamides) via palladium-catalyzed aminocarbonylation.
abstract: 3,17-Dicarboxamido-androst-3,5,16-triene derivatives possessing various amine moieties were synthesized under mild conditions using palladium-catalyzed homogeneous aminocarbonylation as key reaction. Compounds containing the corresponding iodoalkene functionalities, i.e., 17-iodo-16-ene and 3-iodo-3,5-diene structural motifs, were used in the aminocarbonylation and the N-nucleophiles were varied systematically. Three amines, such as tert-butylamine, piperidine and methyl alaninate were used as N-nucleophiles in the aminocarbonylation. All variations of 3,17-dicarboxamides were synthesized using this methodology. Androst-4-ene-3,17-dione was used as starting material. The synthetic strategy of the multistep synthesis was based on the systematic variation and consecutive use of three different reactions: (i) the protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, (ii) the transformation of the other keto group to iodoalkene functionality via its hydrazone, and (iii) palladium-catalyzed aminocarbonylation of the iodoalkene functionality.
authors.affiliation: Department of Inorganic Chemistry and Szentágothai Research Center, University of Pécs, Ifjúság u. 6, H-7624 Pécs, Hungary.
authors.forename: Mercédesz
authors.initials: M
authors.lastname: Kiss
authors.forename: Noémi
authors.initials: N
authors.lastname: Pálinkás
authors.forename: Attila
authors.initials: A
authors.lastname: Takács
authors.forename: Sándor
authors.initials: S
authors.lastname: Mahó
authors.forename: László
authors.initials: L
authors.lastname: Kollár
mesh_terms: D058891:5-alpha Reductase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D000731:Androstanes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D058891:5-alpha Reductase Inhibitors; D000731:Androstanes; D010165:Palladium; C033936:androstane