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Paper | Regular issue | Vol 41, No. 9, 1995, pp.2033-2042
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7151
Synthesis of Perhydro-1,3,4-thiadiazin-5-ones and 3-Arylaminothiazolidin-4-ones by the Regioselective Cyclocondensation of 2-Sulfanylalkanoic Acids or Their Silyl Esters with Methyl and Aryl Hydrazones

Yoo Tanabe, Masaki Nagaosa, and Yoshinori Nishii

*School of Science, Kwansei Gakuin University, 1-1-155 Uegahara, Nishinomiya, Hyogo 662, Japan


Perhydro-1,3,4-thiadiazin-5-ones and 3-arylaminothiazolidin-4-ones were prepared by the highly regioselective cyclocondensation of 2-sulfanylalkanoic acids with methyl- and arylhydrazones, respectively. A similar reaction using trimethylsilyl 2-sulfanylalkanoates in the place of the acids proceeded under milder conditions with tetrabutylammonium fluoride catalyst.