Synthesis of steroidal diacyl hydrazines and their 1,3,4-oxadiazole derivatives

Zsolt Szarka, Rita Skoda-Földes, Judit Horváth, Zoltán Tuba, László Kollár

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19 Citations (Scopus)

Abstract

Homogeneous catalytic hydrazinocarbonylation of some steroid derivatives possessing iodo-alkenyl moiety (17-iodo-androst-16-ene 1, 17-iodo-3-methoxy-estra-1,3,5(10),16-tetraene 2, 17-iodo-4-aza-4-methyl-androst-16-en-3-one 3 and 17-iodo-6β-hydroxy-3α,5α-cycloandrost-16-ene 4) were carried out in the presence of a palladium catalyst, a base and acetic or benzoic hydrazide as the nucleophilic reagent. The corresponding N-acetamido-carbamoyl 1a-4a or N-benzamido-carbamoyl derivatives 1b-4b were obtained in high yields. Some of these derivatives served as starting materials for the synthesis of new steroidal 1,3,4-oxadiazole compounds.

Original languageEnglish
Pages (from-to)581-586
Number of pages6
JournalSteroids
Volume67
Issue number7
DOIs
Publication statusPublished - May 13 2002

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Keywords

  • 17-Iodo-androst-16-ene derivatives
  • Carbonylative coupling reaction
  • Diacyl hydrazines
  • Palladium catalysts
  • Steroids

ASJC Scopus subject areas

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

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