• YAKHAK HOEJI
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• v.32 no.4
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• pp.245-250
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• 1988

Naphthoquinone derivatives have been found to be anticoagulant. In this report, several new 2-chloro-3-(N-arylamino)-naphthoquinone derivatives were synthesized in oder to develope mild anticoagulant. 2, 3-dichloro-1, 4-naphthoquinone was reacted with p-aminobenzoic acid, m-aminobenzoic acid, toluidine, m-nitroaniline, sulfanilamide, sulfathiazole, sulfaguanidine, phenetidine, 2-aminopyrimidine and 3-amino-5-methylisoxazole in EtOH or AcOH afford 2-chloro-3-(p-carboxy anilino)-naphthoquinone (1), 2-chloro-3-(m-carboxyanilino)-naphthoquinone (2),2-chloro-3-(toluidino)-naphthoquinone (3),2-chloro-3-(m-nitroanilino)-naphthoquinone (4), 2-chloro-3-(4-sulfanilanilino)-naphthoquinone (5), 2-chloro-3-(4-sulfathiazolino)-naphthoquinone (6),2-chloro-3-(4-sulfaguanidino)-naphthoquinone (7),2-chlro-3-(phenetidino)-naphthoquinone (8), 2-chloro-3-(pyrimidine-2-amino)-naphthoquinone (9) and 2-chloro-3-(5-methylisoxazole-3-amino)-naphthoquinone (10) in good yield.

• YAKHAK HOEJI
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• v.5 no.1
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• pp.56-57
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• 1960

Three new 5-chloro-8-quinolinol derivatives such as 5-chloro-7-[4-(2-N-pyrrolidylethyl)-1-piperidylmethyl]-8-quinolinol 5-chloro-7-[4-(2-N-piperidylethyl)-1-piperidylmethyl]-8-quinolinol and 5-chloro-7-[4-(2-N-morpholinylethyl)-1-piperidylmethyl]-8-quinolinol were synthesized and found to be effective against Entamoeba histolytica in vitro and against experimental intestinal amebiasis in rats.

• Journal of the Korean Chemical Society
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• v.42 no.4
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• pp.449-453
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• 1998

The reaction of 6-chloro-2-hydrazinoquinoxaline 4-oxide (11) with ethyl chloroglyoxylate provided ethyl 8-chloro-4H-1,3,4-oxadiazino[5,6-b]quinoxaline-2-carboxylate (12) through the intramolecular cyclization. The reaction of 12 with hydrazine hydrate afforded the $C_2$-hydrazinocarbonyl derivative 13, whose reactions with substituted benzaldehydes or heteroaryl aldehydes provided 8-chloro-2-(substituted benzylidenehydrazinocarbonyl)-4H-1,3,4-oxadiazino[5,6-b]quinoxalines (14) or 8-chloro-2-[(2-substituted methylidene)hydrazinocarbonyl]-4H-1,3,4-oxadiazino[5,6-b]quinoxalines(15), respectively.

• The Korean Journal of Pesticide Science
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• v.8 no.1
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• pp.1-7
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• 2004

Fenoxaprop-p-ethyl[Ethyl (R)-2-{4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate] is well known as a herbicide for its specific activity against the weed grasses. This compound was synthesized by the reaction of 4-(6-chloro-1,3-benzoxazol-2-yloxy)phenol and ethyl (S)-O-(p-toluenesulfonyl)lactate in good yields with high optical pure(optical purity: 99.9% up). In this process Walden inversion occurs, whereby the S-configuration of the propionic acid derivative is converted to the R-configuration of the final product. 4-(6-Chloro-l,3-benzoxazol-2-yloxy)phenol was obtained by 5 step reactions in over-all 70% yields using inexpensive raw materials.

• Journal of the Korean Chemical Society
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• v.44 no.3
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• pp.229-236
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• 2000

The reaction of 6-chloro-2-hydrazinoquinoxaline 4.oxide(10) with acetylacetone or dibenzoylmethane gave 6-chloro-2-(3,5-disubstituted pyrazol-1-yl)quinoxaline 4-oxides (11) through the intramolecular·cyclization.The chlorination of compound 11 with phosphoryl chloride afforded 3,6-dichloro-2-(3,5-disubstituted pyrazol-1-yl)quinoxalines (12), whose reaction with hydrazine hydrate provided 6-chloro-3-hydrazinodehydes, benzenesulfonyl chloride, substituted benzoyl chlohdes or acyl chlorides gave novel pyrazolylquinoxalines (14-17).

• Journal of the Korean Chemical Society
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• v.21 no.3
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• pp.180-186
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• 1977

The preparation of 1-chloro-2-iodoperfluorocycloalkenes was achieved with a short reaction time and a high yield when the starting compound was iodinated via the metalation process using an alkyllithium reagent. Especially, the high yield of 1-chloro-2-iodo-perfluorocyclohexene was obtained when 1,2-dichloroperfluorocyclohexene was iodinated via the same reaction conditions. The coupling reaction of 1,2-dihaloperfluorocycloalkenes was also achieved with a lower reaction temperature and a shorter reaction time when the equal slurry mixture of fluorocycloolefines and DMF was reacted at a high pressure in a sublimer. The yield of the coupling product was greatly improved by this process. For a typical example, the coupling reaction of the 1-chloro-2-iodotetrafluorocyclobutene was proceeded with a higher yield of the product than that of the reported reaction, when the present method was adopted. A plausible reaction mechanism of the present coupling reactiont was proposed and the physical characteristics of the coupling product were confirmed.

• YAKHAK HOEJI
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• v.34 no.1
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• pp.15-21
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• 1990

-4,9-dione derivatives were prepared from $2-chloro-3-({\alpha}-accetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. $2-Chloro-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ was reacted with amines to give $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ derivatives. Subsequent treatment of $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium ${\alpha}-cyano$ ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.

• The Korean Journal of Pesticide Science
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• v.9 no.1
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• pp.23-25
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• 2005

3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole, which is the key intermediate of cyclic imide type compounds such as EK 5439 and S-275 series, were practically synthesized by the procedure of hydrolysis of by-products and were produced in the reaction of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydroindazol-3-one with phosgene.

• Archives of Pharmacal Research
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• v.27 no.12
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• pp.1189-1193
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• 2004

The total synthesis of norneolignans isolated from Krameria species, 2-aryl-5-(E)-propenylbenzofurans (5, 11), is described. The key step involves the one-pot reaction for 2-arylbenzofurans (2, 7) from 4-hydroxyphenylacetone with 4'-acetoxy-2-chloro-2-(methylthio)acetophenone (1) and 2-chloro-2-methylthio-(2',4',6'-trimethoxy)acetophenone (6) under Friedel-Crafts reactionconditions.

• Journal of the Korean Chemical Society
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• v.40 no.11
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• pp.681-685
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• 1996

New 6-cyanomethyl-1,3,5-triazine derivatives 4 containing amino, n-propylamino, isopropylamino and anilino groups at 2-and 4-position on the 6-cyanomethyl-1,3,5-triazine ring were prepared from 6-chloro-l,3,5-triazine derivatives 2' and 3 with tert-butyl cyanoacetate. The derivatives of 6-chloro-l,3,5-triazine 2' and 3 containing amino, n-propylamino, isopropylamino and anilino groups at 2- and 4-position on the 6-chloro-1,3,5-triazine ring were prepared from 2,4,6-trichloro-1,3,5-triazine as well as 4,6-dichloro-1,3,5-triazine derivatives 2 with amine derivatives.