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DOI: 10.1055/s-2006-942524
Ring Strain and Weak Bonds: Δ2-1,2-Diazetines as Building Blocks for Pyridazines
Publication History
Publication Date:
25 July 2006 (online)
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
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References
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].