• YAKHAK HOEJI
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• v.41 no.4
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• pp.473-479
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• 1997

New cephalosporin antibiotics, 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 2a-2d, 7 -[(3,4-dihydro-6-ethoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido] -3-substituted-3-cephem-4-carboxylic acid derivatives 3a-3d and 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)-oxide)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 4a-4d were synthesized. Antibacterial activities of these new cephalosporin derivatives and the relationship between their structures and their activities were examined. Among them, 7-[(3,4-dihydro-6-methoxycaronyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)oxide)-acetamido]-3-[(1,2,3-triazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid 4d exhibited the antibacterial activities against Gram(+)and Gram(-) bacteria.

• Bulletin of the Korean Chemical Society
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• v.9 no.3
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• pp.164-166
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• 1988

7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (I) or (-) resonance (R), (-) inductive (I) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (I) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.

• Journal of the Korean Chemical Society
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• v.38 no.7
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• pp.521-525
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• 1994

New cephalosporin antibiotics, 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-heterocyclothiomethyl-3-cephem-4-carboxylic acid derivatives(2a∼2d) were synthesized. Antibacterial activities of these new cephalosporin derivatives and the relationship between their structures and their activities were examined. Among them,7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-[(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid exhibited the broad antibacterial activities against Gram(+) and Gram(-) bacteria.

• 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.

• YAKHAK HOEJI
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• v.37 no.2
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• pp.136-142
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• 1993

To a suspension of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-{3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl}-4-oxo-3-quinoline carboxylic acid(C1) in sodium hydroxide solution and water is added dropwise with stirring carbon disulfide. [6R-[6$\alpha$, 7$\beta$(Z)]]-7-[[[2-Amino-4-thiazoly)methoxyimino]-acetyl]amino]-3-[[[[7-( 3-carboxy-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-guinolonyl)-3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]thioxomethyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (DACD) was synthesized from 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[7-(mercapto) thioxomethyl-[3,7-dia zabicyclo[3.3.0]oct-1(5)-en-3-yl}]-4-oxo-3-quinoline carboxylic acid disodium salt(C2) and cefotaxime. The invitro activity of novel dual-action cephalosporin, DACD, was compared with the in vitro activities of CENO(cefotaxime 3'-norfloxacin dithiocarbamate), cefotaxime, and norfloxacin against a variety of bacterial species. In vitro activity of DACD was superior to that of norfloxacin against Streptococcus pyogenes. Against Gram-positive and Gram-negative bacteria, its activity was almost equal to that of CENO.

• The Korean Journal of Pesticide Science
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• v.4 no.2
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• pp.69-71
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• 2000

The herbicidal activities ($pI_{50}$) with alkoxy (RO-) groups on the azomethine nitrogen atom in 5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one derivatives against various weeds were measured in the flooded and in the paddy conditions. Particularly, i-propoxy subsutuent, 5 of them showed excellent herbicidal activity at a rate of 4kg/ha with pre-emergence against barnyard grass (Echinochloa crus-galli) with good selectivity on rice plant (Oryza sativa). The results of the structure-activity relationships (SAR) analyses are shown that the alkyl subsituents with higher hydrophobicity (logp>0) and electron donating (${\sigma}^*<0$) group as a new substrate rather than alkoxy substituents seems to be contribute to the herbicidal activity with pre-emergence.

• YAKHAK HOEJI
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• v.31 no.1
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• pp.14-18
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• 1987

2-Substituted-3, 4-dihydro-2H-1, 2-benzothiazin-4-one 1, 1-dioxide 6 was reatced with magnesium methyl carbonate to form magnesium chelate 7, which could be hydrolized in cold hydrochloric acid solution to give 2-substituted-4-hydroxy-2H, 1, 2-benzothiazine-3-Carboxylic acid 1, 1-dioxide 2 in good yield.

• Bulletin of the Korean Chemical Society
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• v.9 no.6
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• pp.359-362
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• 1988

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with 1,3-diketones or 1,3-dialdehydes in polyphosphoric acid gave 6,9-dihydro-6,9-dioxopyridazino [1,2-a][1,2,3]triazines (3-6) and 6,11-dihydro-6,11-dioxo[1,2,3]triazino[1,2-b]phtha lazines (7-10), respectively. The condensation of 2 with 2,4-pentanedione in acetic acid gave N-alkylidene intermediate (11), which was cyclized to 9 by treatment with polyphosphoric acid.

• The Korean Journal of Pesticide Science
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• v.5 no.3
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• pp.12-17
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• 2001

A new 2,3-dihydro-2,3,4,6,7-pentamethylbenzofuran-5-yl substituents in 5-benzofuryl-2-[1-(alkoxyimine) alkyl]-3-hydroxycyclohex-2-en-1-ones were found to have herbicidal activity against rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) under submerged conditions. The structure activity. relationships (SARs) on the herbicidal activity of $R_1\;and\;R_2$ on the azomethine bond of 2,3-dihydro-2,3,4,6,7-pentamethylbenzofuran-5-yl subsituents were analysized. The conditions of the selective herbicide activity between rice plant (seed) and barnyard grass from the basis on the analysized SARs are assumed that the $R_2$ group of ethyl substituent ($R_1$ ) should have optimal asymmetry parameter, $(L/B_1)_{opt.}=3.96{\AA}$. And also, the $R_2$ groups consist of $C_1{\sim}C_3$ and unsaturated group such as 3-chloro-2-propenyl group was contribution to the herbicide activity.

• Journal of the Korean Chemical Society
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• v.40 no.7
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• pp.526-530
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• 1996

3-(N-Alkylamino)-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxides have been prepared by the treatment of 3-imino-1,2,5-thiadiazolidine 1,1-dioxides with alkylamines. The selected spectral properties of these heterocycles are detailed, as well as an X-ray crystallographic structure of a representative member of these compounds. 3-(N-Benzylamino)-4,5-dihydro-4-(4'-methoxyphenyl)-1,2,5-thiadiazole 1,1-dioxide crystallyzes in space group $P2_1a$, monoclinic, with $a=22.512(3)(1)\AA$, $b=9.831(2)\AA$, $c=7.194(4)\AA$, $\beta=96.65(2)$, and Z=4.