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DOI: 10.1055/s-2007-983834
Synthesis and Structure of Thia and Selena Heterocycles Containing Cycloamidine Substructures
Publication History
Publication Date:
08 August 2007 (online)
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Abstract
Cyclization of a bis-arylimidoyl chloride with an acylselenourea leads to the construction of a 1,3-selenazolidine with a heteroradialene structure. Another reaction of the bis-arylimidoyl chloride (hydrazinolysis) leads to the formation of Δ2-1,2-diazetines, which we have shown previously to be reactive precursors for ring transformation reactions that yield unusual heterocycles. We now demonstrate that the reaction of these Δ2-1,2-diazetines with various isothio- or isoselenocyanates affords an efficient entry to highly substituted 1,3,4-thia- or -selenadiazines. The structures of these novel derivatives were confirmed by NMR and mass spectroscopy, elemental analysis, and X-ray structural analysis. Detailed multidimensional 77Se NMR experiments as well as density functional theory (DFT) calculations show structural specifics of these compounds.
Key words
ring expansion - heterocycles - selenium - sulfur - noncovalent chalcogen interactions
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CCDC-644462 (3), CCDC-644463 (7g), and CCDC-644464 (8j) 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; email: deposit@ccdc.cam.ac.uk).