Synthesis of Azabicyclo[2.2.n]alkane Systems as Analogues of 3-[1-Methyl-2-(S)-pyrrolidinylmethoxy]pyridine (A-84543)
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Universidad de La Rioja
info
ISSN: 0022-3263
Year of publication: 2007
Volume: 72
Issue: 8
Pages: 3112-3115
Type: Article
More publications in: Journal of Organic Chemistry
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Abstract
(Chemical Equation Presented) This work is connected with the epibatidine field and describes the synthesis of several analogues of compounds that present affinity for nicotinic acetylcholine receptors, such as 3-[1-methyl-2-(S)- pyrrolidinylmethoxy]pyridine (A-84543). These analogues bear a 3-pyridyl ether substituent at the bridgehead carbon of the azabicyclo[2.2.n]alkane system. Particularly, in the case of the 1-substituted 2-azabicyclo-[2.2.2]octane system, a new synthetic route has been developed, which involves the synthesis of a novel rigid sulfamidate that allows the straightforward introduction of nucleophiles. © 2007 American Chemical Society.