Synthesis and Structure of Thia and Selena Heterocycles Containing Cycloamidine Substructures
SYNTHESIS-STUTTGART(2007)
摘要
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 Delta(2)-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 Delta(2)-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 Se-77 NMR experiments as well as density functional theory (DFT) calculations show structural specifies of these compounds.
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关键词
ring expansion,heterocycles,selenium,sulfur,noncovalent chalcogen interactions
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