182552-86-9Relevant academic research and scientific papers
Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists
Knoops, Nele,Deroover, Geert,Jidong, Zhang,Compernolle, Frans,Hoornaert, Georges J.
, p. 12699 - 12716 (1997)
A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles.
A versatile stereospecific synthesis of the 1,3-disubstituted benzo[a]quinolizidine framework via 2-aryl substituted pyridines
Van der Eycken, Erik,Deroover, Geert,Toppet, Suzanne M.,Hoornaert, Georges J.
, p. 9147 - 9150 (2007/10/03)
The stereospecific synthesis of the 1,3-disubstituted benzo[a]quinolizidine 6 is described starting from the easily accessible 3-arylated-6-substituted oxazinone 2. The skeleton is elaborated via an intramolecular aromatic substitution on the α-amino aldehyde obtained by treatment of the intermediate piperidine 4 with glycidol and consecutive oxidative cleavage of the diol.
