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Paper | Special issue | Vol 74, No. 1, 2007, pp.683-700
Published online, 12th October, 2007
DOI: 10.3987/COM-07-S(W)54
Synthesis of Benzylisoquinoline Derivatives Possessing Electron-Withdrawing Substituents on the Benzene Ring of the Isoquinoline Skeleton

René Severin, Didin Mujahidin, Jessica Reimer, and Sven Doye*

*Institute of Pure and Applied Chemistry, University of Oldenbrug, Carl-von-Ossietzky-Str. 9-11, D-26111 Oldenbrug, Germany


3,4-Dihydrobenzylisoquinolines and 1,2,3,4-tetrahydrobenzyl- isoquinolines possessing electron withdrawing substituents on the benzene ring of the isoquinoline framework are easily accessible by a synthetic approach that takes advantage of a Sonogashira coupling to build up the C1-C8a bond of the isoquinoline skeleton and a Ti-catalyzed intramolecular hydroamination of an alkyne to close the heterocyclic ring.