• 대한화학회지
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• 제55권2호
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• pp.230-234
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• 2011

4,5-Dihydro-6-(4-methoxy-3-methylphenyl)-3(2H)-pyridazinone derivative계 화합물의 합성연구를 수행하였다. 첫 번째로, 4,5-dihydro-6-(4-methoxy-3-methylphenyl)-3(2H)-pyridazinone (1)은 o-cresyl methyl ether와 succinic anhydride를 Friedel-Crafts 아실화 반응을 통하여 얻은 다음에, 고리화 반응을 통하여 합성하였다. 얻어진 화합물 1을, NaOEt조건 하에서, 방향족 알데히드와 반응시켜서 4-substituted benzyl pyridazinones (3a-d)을 합성하였으며, 화합물 1을 탈수소화반응을 시켜서 화합물 4를 얻었다. 한편 pyridazine 5는 화합물 1과 1,3-diphenyl-2-propen-1-one을 Michael 첨가반응을 이용하여 합성하였다. N-Dialkylaminomethyl 화합물 6a-b는 pyridazinone 1과 formaldehyde 및 2차 amine을 바능시켜서 얻은 반면에, 화합물 7은 pyridazinone 1을 반응시켜서 얻었으며, 화합물 8은 pyridazinone 3b를 phosphorus oxychloride 와 반응시켜서 얻었다.

• Archives of Pharmacal Research
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• 제27권1호
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• pp.13-18
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• 2004

In this study, 6-[( 4-arylidene-2-phenyl-5-oxoimidazolin-1-yl)phenyl]-4,5-dihydro-3(2H)-pyridazinone and 4-[(4-arylidene-2-phenyl-5-oxoimidazolin-1-yl)phenyl]-1(2H)-phthalazinone derivatives were synthesized by reacting 6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone or 4-(4-aminophenyl)-1(2H)-phthalazinone compound with different 4-arylidene-2-phenyl-5(4H)-oxazolone derivatives. The vasodilator activities of the compounds were examined both in vitro and in vivo. Some pyridazinone derivatives showed appreciable activity.

• 대한화학회지
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• 제14권1호
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• pp.61-64
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• 1970

trichloroethylideneacetophenone과 hydrazine hydrate의 반응으로 3-phenyl-5-trichloromethyl-2-pyrazoline을 합성하였다. 또한 trichloroethylideneacetophenone과 phenylhydrazine 또는 치환된 phenylhydrazine의 반응으로 pyridazinone 유도체들을 합성하였다.

• Archives of Pharmacal Research
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• 제28권5호
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• pp.509-517
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• 2005

A series of structurally diverse amide derivatives of [6-(3,5-dimethyl-4- chloro-pyrazole-1-yl)-3(2H)-pyridazinone-2-yl]acetic acid were prepared and tested for their in vivo analgesic and anti-inflammatory activity by using p-benzoquinone-induced writhing test and carrageenan induced hind paw edema model, respectively. The analgesic and anti-inflammatory activity of the compounds, 7c, 7d and 7k were found to be equipotent to aspirin (as an analygesic) and indometacin (as an anti-inflammatory drug), respectively. The other amide derivatives generally resulted in lower activity on comparision with reference compounds.

• 대한화학회지
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• 제16권3호
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• pp.189-192
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• 1972

2, 6-Disubstituted-3-pyridazinones were synthesized from the reaction of trichloroethylideneacetophenone with substituted phenylhydrazines. Trichloroethylideneacetophenone 2, 4-dinitrophenylhydrazone was isolated from the reaction of trichloroethylideneacetophenone with 2, 4-dinitrophenylhydrazine and it gave 2-(2, 4-dinitrophenyl)-6-phenyl-3-pyridazinone through ring closure. This indicates that pyridazinones are produced through hydrazone formation and ring closure as suggested previously. The effect of substituents of phenylhydrazine on the reaction was also discussed.

• 대한화학회지
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• 제16권4호
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• pp.229-231
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• 1972

2, 6-Disubstituted-3-pyridazinones were synthesized from the reaction of trichloroethylideneacetone with substituted phenylhydrazines. From the reaction of trichloroethylideneacetone with ο-nitrophenylhydrazine, pyridazinone derivative was not obtained, but ${\gamma},{\gamma}$-dichloro-${\gamma}$-(o-nitrophenylhydrazino)-ethylideneacetone was obtained in 24% yield.

• 약학회지
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• 제57권5호
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• pp.316-322
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• 2013

The new pyridazinone analogs were synthesized for development of candidates to retain anticancer activity. Various 6-substituted pyridazin-3(2H)-ones were prepared from the pyridazinyl chloride 3a~d via endothermic nucleophilic substitution with hydroxide ion as nucleophile for 2~48 h. Pyridazinyl chloride 3a~d could be converted to hydroxypyridazines (or pyridazin-3(2H)ones) using 1~5 equivalents of water (or 1 equivalent of sodium hydroxide) at reflux in DMF. The tautomerism of lactim form to lactam form was also accomplished in pyridazine derivatives. Formation of pyridazinones 10 was undertaken with stirring using sodium hydroxide at reflux in DMF for 2 h. Synthetic compounds were identified using NMR spectrum.

• 대한화학회지
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• 제19권1호
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• pp.38-42
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• 1975

2-Acetothienone과 chloral을 축합시켜 chloral-2-acetothienone을 생성하였으며 이것을 탈수하여 trichloroethylidene-2-acetohienone을 합성하였다. Trichloroethylidene-2-acetothienone과 phenylhydrazine 또는 치환된 phenylhydrazine들과의 반응으로 2-aryl-6-(2-thienyl)-3(2H)-pyridazinone들을 얻었으며 hydrazine과의 반응에서는 3-(2-thienyl)-5-trichloromethyl-2-pyrazoline이 합성되었다.

• Bulletin of the Korean Chemical Society
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• 제24권11호
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• pp.1655-1658
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• 2003

Chemoselective N-benzenesulfonylation of aliphatic amines using 2-(4-nitrobenzenesulfonyl)-4,5-dichloropyridazin-3(2H)-one (2) gave the corresponding 4-nitrobenzenesulfonamides in good or excellent yield. This method is a simple, mild and general procedure for the chemoselective N-benzenesulfonylation of aliphatic amines.

• 대한화학회지
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• 제17권1호
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• pp.25-30
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• 1973

$\gamma$,$\gamma$,$\gamma$-Trichloroethylidene-m-Nitroacetophenone과 phenylhydrazine및 치환된 phenylhydrazine들과의 반응으로 2,6-disubstituted-3-pyridazinone들을 합성하였으며 2,4-dinitrophenylhydrazine과의 반응에서는 hydrazone을 중간체로 분리하였다. hydrazinehydrate와의 반응에서는 3-(mnitrophenyl)-5-trichloromethyl-2-pyrazoline이 좋은 수득률로 얻어졌다. 또한$\gamma$,$\gamma$,$\gamma$-trichloroethylidene-m-nitroacetophenone과 치환된 phenylhydrazine과의 반응에서 phenyl기에 결합된 치환기의 효과를 검토하였다.