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Communication | Regular issue | Vol 22, No. 8, 1984, pp.1667-1672
Published online, 1st January, 1970
DOI: 10.3987/R-1984-08-1667
Synthesis and Structure of a 1,2,5,7-Benzothiatriazonine

Marlise Schläpfer-Dähler, Roland Prewo, Jost H. Bieri, and Heinz Heimgartner*

*Organische-chemisches Institut, Universitat Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switerland


3-Dimethylamino-2,2-dimethyl-2H-azirine (1) and 4-phenyl-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxide (6) react already below room temperature to give a nine-membered heterocyclic product, namely 3-dimethylamino-4,4-dimethyl-7-phenyl-4,5,6,7-tetrahydro-l,2,5,7-benzothiatriazonin-6-on-1,1-dioxide (7, Scheme 2) in a quantitative yield. The structure of this new heterocycle has been confirmed by X-ray crystallographic analysis (Fig. 1 and 2). In Scheme 2 a reaction mechanism for the formation of 7 is discussed, the zwitterion b being the key intermediate.