Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and D-homosteroids by intramolecular cyclization reactions.
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.
Magyar
Angéla
A
Department of Organic Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 8., Hungary.
Wölfling
János
J
Kubas
Melanie
M
Cuesta Seijo
Jose Antonio
JA
Sevvana
Madhumati
M
Herbst-Irmer
Regine
R
Forgó
Péter
P
Schneider
Gyula
G
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
D006718:Homosteroids; D011804:Quinolines; D013256:Steroids