Palladium-catalyzed diaminocarbonylation: Synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

Mercédesz Kiss, Sándor Mahó, Katalin Böddi, Borbála Boros, László Kollár

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Novel androstene-based dimers linked through A- and D-ring with 3,3′- and 17,17′-dicarboxamide spacers, were synthesized via palladium-catalyzed aminocarbonylation. Androstane derivatives possessing either 3-iodo-3,5-diene or 17-iodo-16-ene functionality were used as substrates in the presence of palladium-phosphine in situ catalysts and aliphatic and aromatic diamines as N-nucleophiles. Since androst-4-ene-3,17-dione was used as starting material, a multistep synthesis including protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, transformation of the other keto group to iodoalkene functionality via its hydrazone, and palladium-catalyzed aminocarbonylation of the iodoalkene functionality was used. In this way, new dimeric compounds possessing a keto functionality were obtained in moderate-to-good isolated yields, via highly chemoselective reactions, under relatively mild conditions. Graphical abstract: [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)357-364
Number of pages8
JournalMonatshefte fur Chemie
Volume146
Issue number2
DOIs
Publication statusPublished - Feb 2015

Keywords

  • Carbonylation
  • Carboxamide
  • Diamines
  • Iodoalkene
  • Palladium catalyst
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

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