title: Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and D-homosteroids by intramolecular cyclization reactions.
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.
authors.affiliation: Department of Organic Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 8., Hungary.
authors.forename: Angéla
authors.initials: A
authors.lastname: Magyar
authors.forename: János
authors.initials: J
authors.lastname: Wölfling
authors.forename: Melanie
authors.initials: M
authors.lastname: Kubas
authors.forename: Jose Antonio
authors.initials: JA
authors.lastname: Cuesta Seijo
authors.forename: Madhumati
authors.initials: M
authors.lastname: Sevvana
authors.forename: Regine
authors.initials: R
authors.lastname: Herbst-Irmer
authors.forename: Péter
authors.initials: P
authors.lastname: Forgó
authors.forename: Gyula
authors.initials: G
authors.lastname: Schneider
mesh_terms: D000818:Animals; D003500:Cyclization; D006718:Homosteroids / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006718:Homosteroids; D011804:Quinolines; D013256:Steroids