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2004
Isoquinoline derivatives
R 0420
Synthesis of 1,2,3,4-Tetrahydroisoquinolines and 2,3,4,5-Tetrahydro-1HCombining Sequential Palladium-Catalyzed ortho Alkylation/
50- 109 -2-benzazepines
Vinylation with Aza-Michael Addition Reactions. — 1-Substituted tetrahydroisoquinolines (IV) and (VI) are obtained by a one-pot sequence involving Pd-catalyzed
alkylation/alkenylation of the iodobenzenes (I) followed by intramolecular aza-Michael cyclization. Application of this sequence to the synthesis of tetrahydrobenzazepines
results first in formation of the alkylation/vinylation products (VIII), which are further
converted into the heterocycles (IX) by treatment with a base. — (FERRACCIOLI*,
R.; CARENZI, D.; CATELLANI, M.; Tetrahedron Lett. 45 (2004) 37, 6903-6907;
Ist. Sci. Tecnol. Mol., I-20133 Milano, Italy; Eng.) — Roy
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