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Synthesis 2009(5): 836-840  
DOI: 10.1055/s-0028-1087805
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Angular 7,8-Pyridazinocoumarins via the Transformation of a Hydroxy Group into a Carbonyl Group

Antigoni Kotali*a, Ioannis S. Lafazanisa, Philip A. Harrisb
a Laboratory of Organic Chemistry, Department of Chemical Engineering, University of Thessaloniki, Thessaloniki 54124, Greece
Fax: +30(231)0996253; e-Mail: kotali@eng.auth.gr;
b GlaxoSmithKline, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA 19426-0989, USA
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Publication History

Received 30 September 2008
Publication Date:
11 February 2009 (online)

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Abstract

The synthesis of angular 7,8-pyridazinocoumarins (2H-pyrano[2,3-f]phthalazin-2-ones) is reported via the oxidation of 8-[1-(acylhydrazono)ethyl]-7-hydroxycoumarin with (diacetoxyiodo)benzene and subsequent treatment of the derived 7,8-diacylcoumarins with hydrazine. The procedure involves transformation of a hydroxy group into an acyl group and formation of a new C-C bond.

Key words

transformation - oxidation - (diacetoxyiodo)benzene - 2H-pyrano[2,3-f]phthalazin-2-ones - angular pyridazinocoumarins - N-acylhydrazones