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KMID : 1059519890330020247
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Journal of the Korean Chemical Society
1989 Volume.33 No. 2 p.247 ~ p.256
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A Study on the Rearrangement of 1,3-Thiazolidine Sulfoxides to Dihydro-1,4-thiazines
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Lee Wha-Suk
Hahn Hoh-Gyu
Mah He-Duck
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Abstract
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4-Acetyl-5,6-dihydro-2-methyl-1,4-thiazine carboxylic acid derivatives 24 were prepared by ring expansion of corresponding thiazolidine sulfoxides. Oxidation of 2-methyl-1,3-thiazolidine-2-acetic acid derivatives 12 gave a mixture of cis and trans sulfoxides, 14 and 15. Assignments of the cis and trans sulfoxides were based on the 1H NMR and IR spectroscopy and regioselectivity of deuterium exchange reaction. With PTSA as acid catalyst both the cis and trans sulfoxide, 14 and 15 were transformed via sulfenic acid 18 to dihydro-1,4-thiazine 24. However, under the neutral conditions (in DMF at 100℃) the trans sulfoxides 15 rearranged via sulfenic acid 21 to isomeric dihydrothiazines 27. The mechanism of formations of 24 and 27 is also discussed.
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