Ring Strain and Weak Bonds: Δ2-1,2-Diazetines as Building Blocks for Pyridazines

J. Fleischhauer; R. Beckert; W. Günther; H. Görls

doi:10.1055/s-2006-942524

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Synthesis 2006(17): 2885-2890
DOI: 10.1055/s-2006-942524

PAPER

Ring Strain and Weak Bonds: Δ²-1,2-Diazetines as Building Blocks for Pyridazines

J. Fleischhauer^a, R. Beckert*^a, W. Günther^a, H. Görls^b
^a Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University, Humboldtstraße 10, 07743 Jena, Germany
^b Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University, Lessingstraße 8, 07743 Jena, Germany
Fax: +49(3641)6948212; e-Mail: Rainer.Beckert@uni-jena.de;

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Publication History

Received 28 April 2006
Publication Date:
25 July 2006 (online)

Abstract
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Abstract

Deprotonated 1,2-diazetines react with various ketones containing an acidic CH to yield pyridazine derivatives. The reaction allows the synthesis of dihydropyridazines containing a cycloamidine substructure via a sequence of ring-opening and recyclization. In this case, the in situ generated anion of 1,2-diazetines acts as a base as well as a chelator. The structures of the novel synthesized derivatives were confirmed by X-ray structural analysis and multidimensional NMR experiments.

Key words

ring expansion - regioselectivity - heterocycles - imines - ketones

References

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CCDC 605533 (3b), 605534 (3n), and 665535 (3p) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].