1107620-31-4Relevant academic research and scientific papers
Synthesis of Quinuclidines by Intramolecular Silver-Catalysed Amine Additions to Alkynes
Breman, Arjen C.,Ruiz-Olalla, Andrea,Van Maarseveen, Jan H.,Ingemann, Steen,Hiemstra, Henk
, p. 7413 - 7425 (2016/02/20)
A new method has been developed for the synthesis of 2-alkylidenequinuclidines based on a silver triflate catalysed intramolecular hydroamination of 4-(prop-2-ynyl)piperidines. Monosubstituted piperidines reacted less efficiently than cis-disubstituted piperidines, and the reaction was selective for an alkyne moiety, even in the presence of a vinyl group at the 3-position. The hydroamination occurred readily with a terminal alkyne, as well as with an internal alkyne bearing an aliphatic or aromatic group at the terminal carbon atom. Using this silver-catalysed cyclization, a short procedure was developed for the relay synthesis of the cinchona alkaloids dihydroquinidine and dihydroquinine. We report the synthesis of (enantiomerically pure) 2-alkylidenequinuclidines by an intramolecular hydroamination reaction catalysed by silver triflate. After cyclization to the appropriate quinuclidines, the cinchona alkaloids dihydroquinidine and dihydroquinine were obtained in a two-step procedure.
NOVEL HETEROCYCLIC DERIVATIVES AS M-GLU5 ANTAGONISTS
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Page/Page column 72, (2009/03/07)
This invention relates to novel heterocyclic compounds having selective affinity for the mGlu5 subtype of metabotropic receptors, pharmaceutical compositions thereof and uses for such compounds and compositions in the treatment of lower urinary tract diso
