Synthesis of steroid-ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation - Copper-catalyzed azide-alkyne cycloaddition reaction sequence

Eszter Szánti-Pintér, János Balogh, Zsolt Csók, László Kollár, Ágnes Gömöry, Rita Skoda-Földes

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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 1H and 13C NMR, IR, MS and elemental analysis.

Original languageEnglish
Pages (from-to)1377-1382
Number of pages6
JournalSteroids
Volume76
Issue number12
DOIs
Publication statusPublished - Nov 2011
Externally publishedYes

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Keywords

  • Aminocarbonylation
  • Copper
  • Cycloaddition
  • Ferrocene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

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