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Paper | Regular issue | Vol 65, No. 6, 2005, pp.1311-1320
Published online, 24th March, 2005
DOI: 10.3987/COM-05-10349
1,2-Diazetines as Useful Tools for Ring Transformation Reactions with Isothiocyanates – A New Entry to 1,3,4-Thiadiazines

Rainer Beckert,* Jan Fleischhauer, Anja Darsen, Jennie Weston,* Stephan Schenk, Ariadna Batista, Ernst Anders, Helmar Görls, Manfred Döring, Daniela Pufky, and Olaf Walter

*Institute for Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Lessingstr. 8, D-07743 Jena, Germany

Abstract

1,2-Diazetines (1) can be acylated with isocyanates (2) to give semicyclic urea derivatives (3). In contrast, isothiocyanates (4) react with 1 under mild conditions to furnish new derivatives of 1,3,4-thiadiazine (5). DFT calculations show that two different mechanistic pathways for this ring transformation are possible. N-Acylation is preferred at lower temperatures; whereas an electrocyclic ring opening/cycloaddition process is possible at higher temperatures.