Abstract
Pyrrolidin-2-yl-groups located at C-4 of 3,4-dihydro- or 1,2,3,4-tetrahydroisoquinolines,
respectively, are lost in the course of dehydrogenation of
these isoquinoline derivatives. However, acyclically substituted isoquinolines,
hydrogenated in ring B, 2-benzyl-4-(l-dimethylaminoethyl)-l,2,3,4-
tetrahydroisoquinoline, e.g., show loss of the amine group only by benzylic
cleavage, affording ...
Abstract
Pyrrolidin-2-yl-groups located at C-4 of 3,4-dihydro- or 1,2,3,4-tetrahydroisoquinolines,
respectively, are lost in the course of dehydrogenation of
these isoquinoline derivatives. However, acyclically substituted isoquinolines,
hydrogenated in ring B, 2-benzyl-4-(l-dimethylaminoethyl)-l,2,3,4-
tetrahydroisoquinoline, e.g., show loss of the amine group only by benzylic
cleavage, affording 4-ethylisoquinoline. Scope and limitation of this
reaction are determined using specifically substituted isoquinolines.
C-4-Pyrrolidin-2-yl-3,4-dihydro- oder 1,2,3,4-tetrahydroisochinoline verlieren
bei der Pd-katalysierten Dehydrierung diese Substituenten, während
offenkettig substituierte ringhydrierte Isochinoline, z.B. 2-Benzyl-4-(ldimethylaminoethyl)-
l,2,3,4-tetrahydroisochinolin nur die Aminfunktion
unter Benzylspaltung zu 4-Ethylisochinolin abspalten. Die Grenzen dieser
Reaktion werden anhand der Dehydrierung speziell substituierter Isochinolin-
Derivate abgesteckt.
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