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Zeitschriftenartikel:

C. Hametner, M. Hemetsberger, M. Treu, K. Mereiter, U. Jordis, J. Fröhlich:
"Addition of nucleophiles to immonium galanthamines";
European Journal of Organic Chemistry, 2 (2005), S. 404 - 409.



Kurzfassung englisch:
Four galanthamine derivs. were converted into immonium bromides by treatment with N-(bromo)succinimide. The nucleophilic addn. of cyanide and methylmagnesium iodide to these galanthaminium halides was studied and the structures and conformations of two products were investigated by NMR spectroscopy and X-ray diffraction. For example, cyanation of (4aS,6R,8aS)-4a,5,9,10-tetrahydro-6-hydroxy-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepinium bromide gave (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-6-hydroxy-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-12-carbonitrile as major product. Galanthamine is known as agent for the treatment of Alzheimer's disease.


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