Synthesis 2007(18): 2839-2848  
DOI: 10.1055/s-2007-983834
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Structure of Thia and Selena Heterocycles Containing Cycloamidine Substructures

Jan Fleischhauera, Rainer Beckert*a, Wolfgang Günthera, Stefan Klugea, Stefan Zahna, Jennie Westona, Dorothea Bergb, Helmar Görlsc
a Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University, Humboldtstrasse 10, 07743 Jena, Germany
b Institute of Physical Chemistry, Friedrich Schiller University, Lessingstrasse 10, 07743 Jena, Germany
c Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University, Lessingstrasse 8, 07743 Jena, Germany
Further Information

Publication History

Received 23 May 2007
Publication Date:
08 August 2007 (online)


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.


Orca - an ab initio, DFT, and semiempirical scf-mo package; see:


Weinhold, F. NBO, version 5; see:˜nbo5/.


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 (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; email: