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Synthesis 2011(1): 97-103  
DOI: 10.1055/s-0030-1258969
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalyzed Reactions Involving 3-Formylchromones and Acetylenedicarboxylates: Efficient Synthesis of Functionalized Benzophenones and Polysubstituted Xanthones

Michael A. Terzidis, Vassilios G. Tsiaras, Julia Stephanidou-Stephanatou*, Constantinos A. Tsoleridis*
Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
Fax: +30(2310)997679; e-Mail: ioulia@chem.auth.gr; e-Mail: tsolerid@chem.auth.gr;
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Publication History

Received 2 August 2010
Publication Date:
09 November 2010 (online)

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Abstract

Organocatalyzed reactions between chromones and acetylenedicarboxylates leading either to xanthone derivatives or to functionalized benzophenones are described. The outcome of the reactions was found to depend both on the nature of the chromone substituents and on the basicity of the organocatalyst.

Key words

DMAP - hetero-Diels-Alder reactions - Friedel-Crafts reactions - organocatalysis - xanthones - zwitterions

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The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from: ftp://davinci.chem.umanitoba.ca/pub/marat/SpinWorks/