57502-47-3Relevant academic research and scientific papers
Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators
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Page/Page column 63, (2009/08/14)
Compounds of Formula I: wherein A, B, D, L, R1, R2, R3, R4, m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.
Intramolecular carbolithiation reactions for the preparation of azabicyclo [2.2.1] heptanes
Coldham, Iain,Fernandez, Joan-Carles,Price, Kathy N.,Snowden, David J.
, p. 3788 - 3795 (2007/10/03)
Tin-lithium exchange and intramolecular carbolithiation (anionic cyclization) have been used to construct the three nitrogen-positional isomers of the azabicyclo[2.2.1]heptane ring system. The 7- azabicyclo[2.2.1]heptane ring system is accessed from either diastereomer of a 2,5-disubstituted pyrrolidine, via a chiral organolithium intermediate. The 2-azabicyclo[2.2.1]heptane ring system is formed stereoselectively in low yield by a tandem cyclization, together with the product from monocyclization. Better yields of the 2-aza ring system can be obtained using an alternative approach from a 2-tributylstannyl-4-allylpyrrolidine, despite the trans arrangement of the tin (and, hence, lithium) atom and the allyl unit. The 1-azabicyclo[2.2.1]heptane ring system is accessed in just three steps from 4-piperidone.
Regio- and Stereoselectivity in Anionic Ring Opening Reactions of 2-Azabicycloheptane Derivatives
Franzisket, Ludwig,Heesing, Albert
, p. 635 - 643 (2007/10/02)
In the regioselective ring opening of 1 via the dianion 1c the intermediacy of 2a is proven by labeling experiments.The regioselective cleavage of the four-membered ring in 3 by LiAlH4 proceeds stereoselectively both in the ring and the side chain positio
