Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and D-homosteroids by intramolecular cyclization reactions

Angéla Magyar, János Wölfling, Melanie Kubas, Jose Antonio Cuesta Seijo, Madhumati Sevvana, Regine Herbst-Irmer, Péter Forgó, Gyula Schneider

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Steroidal aryliminium salts were prepared from D-seco-pregnene aldehyde 2b, and their BF3·OEt2-catalyzed reactions were studied. The nature of the substituent R1 in the anilines 3-6 essentially influenced the chemoselectivity. Using unsubstituted 3, 4-methoxy- (4) or 4-bromoaniline (5), different tetrahydroquinoline derivatives 7a-13a via intramolecular hetero Diels-Alder reaction were formed. In the case of 4-nitroaniline (6) the N-arylamino-D-homopregnane (14a) were also obtained. We assume, that an intramolecular Prins reaction led to this type of fluoro-D-homosteroid. The main products represent a new class of tetrahydroquinolino-androstenes.

Original languageEnglish
Pages (from-to)301-312
Number of pages12
JournalSteroids
Volume69
Issue number5
DOIs
Publication statusPublished - May 1 2004

Keywords

  • Cycloaddition
  • D-Homosteroids
  • Hetero Diels-Alder reaction
  • Intramolecular Prins reaction
  • Quinolines

ASJC Scopus subject areas

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

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