81978-78-1Relevant academic research and scientific papers
Reductive transformations of unsaturated azabicyclic nitrolactams
Pilipecz, Mihály Viktor,Varga, Tamás Róbert,Scheiber, Pál,Mucsi, Zoltán,Fàvre-Mourgues, Amélie,Boros, Sándor,Balázs, László,Tóth, Gábor,Nemes, Péter
, p. 5547 - 5553 (2012/09/07)
Using different reducing methods unsaturated indolizidine and quinolizidine lactams substituted with a nitro group were transformed into various alkaloid-like derivatives. Hydrogen transfer and palladium catalyzed hydrogenation gave compounds of ketolactam or lactam type meanwhile the nitro group was eliminated. On the other hand, in presence of Raney-nickel catalyst the nitro compounds were reduced to diastereomeric amino derivatives whose stereochemistry was elucidated by NMR spectroscopy. Using sodium bis-dimethoxy-ethoxy-aluminum-hydride (Red-Al) as reducing agent an unexpected tricyclic azetidine was isolated and characterized.
