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Synthesis 1988; 1988(7): 521-524
DOI: 10.1055/s-1988-27623
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Synthese von 1,4,3-Oxathiazin-4,4-dioxiden und 1,2,4-Thiadiazin-1,1-dioxiden aus 1,3-Acetonbis(sulfonylchlorid)

Walter Ried* , Gernfried Beller, Jan W. Bats
  • *Institut für Organische Chemie der Universität Frankfurt/M., Laboratorium, Niederrad,Theodor-Stern-Kai 7, D-600 Frankfurt, Main 70, Federal Republic of Germany
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Publikationsdatum:
18. September 2002 (online)

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Synthesis of 1,4,3-Oxathiazine-4,4-dioxides and 1,2,4-Thiadiazine-1,1-dioxides from 1,3-Acetonebis(sulfonylchloride) 1 reacts with N,N-dialkylcyanamides 2 at 80°C to give the 1,4,3-oxathiazine 4,4-dioxides 5a-e, which are converted with N- and S-nucleophiles 6 to the substitution products 7a-f. At room temperature 1 reacts with 2 and amines 8 to the sulfonamides 9a-i. The 1,2,4-thiadiazine 1,1-dioxides 10a-c are obtained from 9e-g and ammonia. X-ray analysis of compound 5a was carried out.