Systematic investigation on the synthesis of androstane-based 3-, 11- and 17-carboxamides via palladium-catalyzed aminocarbonylation

Péter Ács, Attila Takács, Mercédesz Kiss, Noémi Pálinkás, Sándor Mahó, László Kollár

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

3,17-Dicarboxamido-androst-3,5,16-triene, 3-carboxamido-androst-3,5-dien- 17-one, 17-carboxamido-androst-4,16-dien-3-one and 11-carboxamido-androst-5, 9(11)-dien-3,17-dione derivatives were synthesized in homogeneous carbonylation reactions from the corresponding 3,17-diiodo-androst-3,5,16-triene, 3-iodo-androst-3,5-diene-17-ethylene ketal, 17-iodo-androst-5,16-dien-3-ethylene ketal, 11-iodo-androst-5,9(11)-diene-3,17-bis(ethylene ketal) derivatives, respectively. A highly chemoselective palladium-catalyzed aminocarbonylation of the corresponding iodo-alkene, carried out under mild reaction conditions, can be considered as the key-step for the introduction of the carboxamide functionalities. The synthesis of the iodo-alkene substrate is based on the transformation of the corresponding keto derivative to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). The aminocarbonylation reaction is highly tolerant towards the N-nucleophiles, i.e. various primary and secondary amines including amino acid methyl esters can also be used.

Original languageEnglish
Pages (from-to)280-290
Number of pages11
JournalSteroids
Volume76
Issue number3
DOIs
Publication statusPublished - Feb 1 2011

Keywords

  • Androstane
  • Carbonylation
  • Carboxamide
  • Iodo-alkene
  • Palladium catalyst

ASJC Scopus subject areas

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

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