773876-52-1Relevant academic research and scientific papers
Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and D-homosteroids by intramolecular cyclization reactions
Magyar, Angela,Woelfling, Janos,Kubas, Melanie,Cuesta Seijo, Jose Antonio,Sevvana, Madhumati,Herbst-Irmer, Regine,Forgo, Peter,Schneider, Gyula
, p. 301 - 312 (2004)
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.
