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Synlett 1996; 1996(9): 820-822
DOI: 10.1055/s-1996-5606
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A Concise Route to Tetrahydrophenanthridinones and Functionalised Isoquinolones

Harry Heaney* , Mutasem O. Taha
  • *Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, Fax +44 (1509) 223925, E-mail h.heaney@lboro.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Reaction of homophthalic anhydride with benzylamine and β-arylethylamine derivatives followed by alkylation, regioselective reduction, and treatment with Lewis acids generate acyliminium ions which, after rearrangement and loss of a proton, give tetrahydrophenanthridinones or isoquinolones.

homophthalic anhydride - homophthalimide - alkylation - acyliminium ion - rearrangement - silyl ketenimide - Pictet-Spengler