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Synfacts 2008(1): 0080-0080  
DOI: 10.1055/s-2007-991441
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Multicomponent One-Pot Synthesis of Functionalized Dihydroisoquinolines

Contributor(s): Paul Knochel, Tobias Thaler
K. Gao, J. Wu*
Fudan University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

This modular multi-component synthesis offers a rapid and facile synthetic access to functionalized 1,2-dihydroisoquinolines. Amines, zinc dust, 2-alkynyl benzaldehydes and benzyl or allyl bromides are the respective components of the reaction. Both the corresponding imine and the organozinc reagent are formed in situ. The final cyclization is catalyzed by Mg(ClO4)2 and Cu(OTf)2. The modular character of the reaction and the good availability of its components open considerable possibilities for variations.