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Synlett 1997; 1997(3): 316-318
DOI: 10.1055/s-1997-778
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Ring-Enlargement Reaction of 3-Alkyl-2-(N-cyanoimino)thiazolidine 1-Oxide: Formation of Novel 5,6-Dihydro-2H-1,2,4-thiadiazin-3(4H)-one Derivatives

Tetsuaki Tanaka1 , Wakako Takase1 , Xie Fang1 , Tsutomu Azuma1 , Shuji Uchida2 , Toshimasa Ishida3 , Yasuko In3 , Chuzo Iwata4
  • 1Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565, Japan
  • 2Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotogecho, Hirakata, Osaka 573-01, Japan
  • 3Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara Takatsuku, Osaka 569-11, Japan
  • 4Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565, Japan, Fax 81 6 879 8214; E-mail iwata@phs.osaka-u.ac.jp
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Publication Date:
31 December 2000 (online)

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The reaction of 3-alkyl-2-(N-cyanoimino)thiazolidine 1-oxides (4) with trifluoroacetic anhydride resulted in a ring-enlargement reaction to give novel 5,6-dihydro-2H-1,2,4-thiadiazin-3(4H)-one derivatives (6).

2-(N-cyanoimino)thiazolidine - 1,2,4-thiadiazine - ring-enlargement - sulfoxide - oxidation