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

Research output: Contribution to journalArticle

14 Citations (Scopus)

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

Fingerprint

Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Palladium
Copper
Steroids
Nucleophiles
Iodides
Ascorbic Acid
Amines
Nuclear magnetic resonance
Catalysts
Chemical analysis
ferrocene
palladium(II) acetate
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • Aminocarbonylation
  • Copper
  • Cycloaddition
  • Ferrocene
  • Palladium

ASJC Scopus subject areas

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

Cite this

Synthesis of steroid-ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation - Copper-catalyzed azide-alkyne cycloaddition reaction sequence. / Szánti-Pintér, Eszter; Balogh, János; Csók, Zsolt; Kollár, László; Gömöry, Ágnes; Skoda-Földes, Rita.

In: Steroids, Vol. 76, No. 12, 11.2011, p. 1377-1382.

Research output: Contribution to journalArticle

Szánti-Pintér, Eszter ; Balogh, János ; Csók, Zsolt ; Kollár, László ; Gömöry, Ágnes ; Skoda-Földes, Rita. / Synthesis of steroid-ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation - Copper-catalyzed azide-alkyne cycloaddition reaction sequence. In: Steroids. 2011 ; Vol. 76, No. 12. pp. 1377-1382.
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AB - 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.

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