• Journal of the Korean Chemical Society
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• v.33 no.2
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• pp.247-256
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• 1989

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 $^1HNMR$ 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 $100^{\circ}C$) the trans sulfoxides 15 rearranged via sulfenic acid 21 to isomeric dihydrothiazines 27. The mechanism of formations of 24 and 27 is also discussed.

• Journal of the Korean Chemical Society
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• v.39 no.11
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• pp.878-880
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• 1995

• Journal of the Korean Chemical Society
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• v.48 no.4
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• pp.443-446
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• 2004

• YAKHAK HOEJI
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• v.41 no.6
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• pp.724-729
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• 1997

New 7-Halo-4-hydroxy-2-allyl-N-3-(4-methoxy-2-carboxylic acid pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide derivatives were synthesized through the condensation of 7-halo-4-hydroxy-2-allyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxide with 4-methoxy L-proline.

• YAKHAK HOEJI
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• v.44 no.6
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• pp.494-498
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• 2000

Noble 7,7'-substituted (or unsubstituted) 4-oxo-1,1',2,2'-dibenzothiazine-3,3'-dicarboxylic acid methyl ester 1,1,1',1'-tetraoxide 3,4'-yl ethers 2a-h were synthesized through the dehydration of 7-substituted (or unsubstituted) 4-hydroxy-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxides 1a-h using silver(I) oxide for the development of new nonsteroidal antiinflammatory drugs (NSAIDs). Optimal reaction was proceeded through stirring of distilled acetone using 100 mol% of silver(I) oxide at room temperature for 24-68 hrs.

• Journal of the Korean Chemical Society
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• v.46 no.5
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• pp.489-492
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• 2002

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.119-130
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• 1993

The stereochemistry of 1,3-thiazolidine sulfoxides 1 in which 3 chiral centres are present in a molecule was elucidated by deuterium exchange and trapping reactions. 3-Acetoxy-1,3-thiazolidines 5 was oxidized to 6 and 8, corresponding $\alpha$-cis 10, $\alpha$-trans 11, $\beta$ -cis 12, and $\beta$ -trans 13 isomers were separated from their diasteromeric mixtures. Sulfoxide 10 was isomerized to more thermodynamically stable isomer 13 under neutral conditions in refluxing benzene or toluene. The methyl hydrogens of 2-methyl group in the sulfoxide 13 and those of the sulfoxide 11 were deuterated by the deuterium incorporation reactions. The intermediate sulfenic acids 25 and 26 derived from the sulfoxides 10 and 12 via sigmatropic rearrangement were trapped by 2-mercaptobenzothiazole (2-MBT) to give disufides 27 and 28 respectively. However, the sulfoxides 11 and 13 were transformed to ring expansion product dihydro-1,4-thiazine 29 under the same reaction conditions. In the presence of acid catalyst, the sulfoxides 10, 11, and 12 were converted to dihydro-1,4-thiazine 29 through the sulfoxide 13 quantitatively. The mechanisms of isomerization of sulfoxides and the formation of 29 were also discussed.

• Journal of the Korean Chemical Society
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• v.46 no.4
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• pp.330-336
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• 2002

For the purpose of development of new agrochemical fungicide of ${\alpha},{\beta}-unsaturated$ carboxanilide series a synthesis of 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-carboxamide (6) is described. Pummerer reaction of sulfoxide 7 obtained by sulfoxidation of dihydro-1,4-thiazine methyl ester 11 gave ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a. Under the same reaction conditions, dihydro-1,4-thiazine carboxanilide sulfoxide 14 was converted to acetoxymethyl dihydro-1,4-thiazine 18 through vinylogous Pummerer reaction involving carboxanilide of sulfonium ion through intermediate 15.1,4-Thiazine carboxanilide 6 was synthesized from the treatment of ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a with acid cat-alyst followed by hydrolysis and then the reaction with aniline.

• Journal of the Korean Chemical Society
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• v.42 no.6
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• pp.657-663
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• 1998

New asymmetric dimer, 7,7'-substituted (or H)-4-oxo-2,2'- dialkyl-l,l',2,2'-dibenzothiazine-3,3'dicarboxylic acid methyl ester-1,1,1',1'-tetraoxide 3,4'-yl ethers 2a-d were synthesized through the oxidative dimerization of 7-substituted (or H)-4-hydroxy-2-alkyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxides la-d using silver oxide($Ag_2O$). 4-Oxo-2,2'-dialkyl-1,1'2,2'-dibenzothiazine-3,3'-dicarboxylic acid methyl ester-1,1,1',l'-tetraoxide 3,4'-yl ether 2c was identified by X-ray crystal structure determination.