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2005
Alkaloids
U 0600
08- 220
1,3-Dipolar Cycloaddition Reactions to Galanthamine Nitrone: An Entry to
4a,5,9,10-Tetrahydro-6H,14aH-benzofuro[3a,3,2-ef]isoxazolo[3,2-a][2]benzazepines. — 1,3-Dipolar cycloaddition of alkynyl and alkenyl dipolarophiles (III) and
(V) to galanthamine nitrone (II) gives rise to the isoxazole anellated compounds (IV),
(VI), and (VII), representing a novel ring system. The reaction of alkynyls (III) with
nitrone (II) proceeds regio- and stereoselectively, while using methylacrylate (Va) and
acrylonitrile (Vb) as reactants, a mixture of four inseparable regio- and stereoisomers
are obtained. The title benzazepines display neither acetylcholine- (AChE) nor
butyryl-choline esterase (BChE) activity, whereas nitrone (II) exhibits low, but selective AChE inhibition. — (HEMETSBERGER, M.; TREU, M.; HAMETNER, C.;
JORDIS, U.; MEREITER, K.; FROEHLICH*, J.; Heterocycles 63 (2004) 10,
2217-2224; Inst. Appl. Synth. Chem., Tech. Univ., A-1060 Wien, Austria; Eng.) —
H. Hoennerscheid
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