Synthesis of ferrocene-labelled steroid derivatives via homogeneous catalytic methods

Eszter Szánti-Pintér, Zsolt Csók, L. Kollár, K. Vékey, R. Skoda-Földes

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Carbonylative Sonogashira coupling and copper catalyzed azide-alkyne cycloaddition were used effectively in the synthesis of ferrocene-labelled steroids. Steroidal alkynyl ketones were obtained in moderate yield from 17-ethynyl steroids without the necessity for the protection of the 17β-OH group of various compounds. Unfortunately, the alkynyl ketone derivatives could not be converted to steroids with heterocyclic groups at C-17 using methylhydrazine cyclocondensation agent. At the same time, 17-triazolyl steroids with ferrocene labels were synthesized in excellent yields starting from the same substrates by a copper-catalyzed azide alkyne cycloaddition. The new compounds were characterized by 1H and 13C NMR, MS and IR.

Original languageEnglish
Pages (from-to)105-107
Number of pages3
JournalJournal of Organometallic Chemistry
Volume718
DOIs
Publication statusPublished - Nov 1 2012

Fingerprint

steroids
Cycloaddition
Ketones
Alkynes
Azides
Steroids
Cycloaddition Reaction
Derivatives
Copper
Heterocyclic Steroids
cycloaddition
Monomethylhydrazine
alkynes
synthesis
ketones
Labels
methylhydrazine
Nuclear magnetic resonance
copper
Substrates

Keywords

  • Carbonylation
  • Copper
  • Cycloaddition
  • Ferrocene
  • Palladium
  • Steroids

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

Synthesis of ferrocene-labelled steroid derivatives via homogeneous catalytic methods. / Szánti-Pintér, Eszter; Csók, Zsolt; Kollár, L.; Vékey, K.; Skoda-Földes, R.

In: Journal of Organometallic Chemistry, Vol. 718, 01.11.2012, p. 105-107.

Research output: Contribution to journalArticle

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AU - Szánti-Pintér, Eszter

AU - Csók, Zsolt

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AU - Skoda-Földes, R.

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AB - Carbonylative Sonogashira coupling and copper catalyzed azide-alkyne cycloaddition were used effectively in the synthesis of ferrocene-labelled steroids. Steroidal alkynyl ketones were obtained in moderate yield from 17-ethynyl steroids without the necessity for the protection of the 17β-OH group of various compounds. Unfortunately, the alkynyl ketone derivatives could not be converted to steroids with heterocyclic groups at C-17 using methylhydrazine cyclocondensation agent. At the same time, 17-triazolyl steroids with ferrocene labels were synthesized in excellent yields starting from the same substrates by a copper-catalyzed azide alkyne cycloaddition. The new compounds were characterized by 1H and 13C NMR, MS and IR.

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