Thia- and Selena-Heterocycles Containing Cycloamidine Substructures: Ring Contraction Reactions of 1,3,4-Thia-/Selenadiazines

Jan Fleischhauer; Rainer Beckert; David Hornig; Wolfgang Günther; Helmar Görls; Vera Klimesova

doi:10.1515/znb-2008-0408

Open Access Published by De Gruyter June 2, 2014

Thia- and Selena-Heterocycles Containing Cycloamidine Substructures: Ring Contraction Reactions of 1,3,4-Thia-/Selenadiazines

Jan Fleischhauer , Rainer Beckert , David Hornig , Wolfgang Günther , Helmar Görls and Vera Klimesova

From the journal Zeitschrift für Naturforschung B

https://doi.org/10.1515/znb-2008-0408

Abstract

1,3,4-Thia/selena-diazines proved to be suitable starting materials for ring contraction reactions. Treatment with acetic acid/water mixtures leads to highly substituted 1,3,4-thia/selenadiazoles. In addition, the selenadiazoles formed undergo a fast Dimroth-rearrangement to finally yield derivatives of 1,2,4-triazole. The structures of all new derivatives were confirmed by NMR experiments, mass spectroscopy, elemental analysis and X-ray structural analysis.

Keywords : Ring Contraction; Dimroth Rearrangement; Triazoles; Thiadiazoles; Selenadiazoles

Received: 2008-1-8

Published Online: 2014-6-2

Published in Print: 2008-4-1

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Thia- and Selena-Heterocycles Containing Cycloamidine Substructures: Ring Contraction Reactions of 1,3,4-Thia-/Selenadiazines

Abstract

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