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Note | Regular issue | Vol 57, No. 3, 2002, pp.523-528
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9427
Synthesis and Structural Assignment of Functionalized 8,9-Diazatricyclo[4.4.0.01,5]decane: A New Tricyclic System Including the Pyridazine Ring

Xavier Cachet, Brigitte Deguin, François Tillequin,* Michel Koch, and Angèle Chiaroni

*Laboratoire de Pharmacognosie,UMR 8638 associee au CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, Avenue de l'Observatoire, 75270 Paris Cedex, France

Abstract

Reaction of hydrazine hydrate with the dipivaloyl ester of (1S, 4R, 5R, 6R)-4-hydroxy-2-hydroxymethyl-1-formylbicyclo[3.1.0]hex-2-ene-6-carboxylic acid (2) afforded (1S, 2R, 4R, 5R, 6R)-8,9-diaza-2-[(2,2-dimethylpropanoyloxy)methyl]-7-oxotricyclo[4.4.0.01,5]dec-9-en-4-yl 2,2-dimethylpropanoate (3). The structure and conformation of the new 8,9-diazatricyclo[4.4.0.01,5]dec-9-ene system were determined by X-Ray cristallography and 2D NMR experiments.