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새로운 1,2,4-Triazole 유도체의 합성에 관한 연구
김호식,박태주,도이향,이만길,창택가구,Kim, Ho Sik,Park Tae Joo,Doh Yi Hyang,Lee Man Kil,Kurasawa Yoshihisa 대한화학회 1992 대한화학회지 Vol.36 No.5
${\circo}-페닐렌디아민(3)을 출발물질로 하여 4단계를 거쳐 {\alpha}-arylhydrazonoacylazide(7)를 합성하였다. 얻어진 {\alpha}-arylhydrazonoacylazide(7)는 디메틸슬폭시드 용액에서 hydrazone imine형과 diazenyl enamine형으로 존재하는데 이들 사이의 토오토메리 현상을 ^1H-NMR 스펙트럼 데이타에 의하여 측정된 토오토머 비로서 고찰하였다. {\alpha}-arylhydrazonoacylazide(7)를 벤젠용매에서 환류시켜 1-aryl-3-quinoxalinyl-1,2,4-triazol(8)을 합성하였다.$ ${\alpha}-Arylhydrazonoacylazide(7) was synthesized starting from {\circo}-phenylenediamine(3) in four steps. The tautomeric behavior of {\alpha}-arylhydrazonoacylazide(7) between the hydrazone imine and diazenyl enamine forms in the dimethyl sulfoxide solution was investigated on the basis of the tautomer ratio determined by the ^1H-NMR spectral data. The 1-aryl-3-quinoxalinyl-1,2,4-triazol(8) was synthesized from {\alpha}-arylhydrazonoacylazide(7) by refluxing in benzene.$
새로운 1-Aryl-3-quinoxalinyl-1,2,4-triazole 의 합성과 α-Arylhydrazonoacylazide 의 토토머화 현상에 관한 연구
鄭周怜,金恩娥,韓盛旭,李萬吉,倉澤嘉久,金浩植 대구효성가톨릭대학교 자연과학연구소 1994 基礎科學硏究論集 Vol.8 No.-
The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydro-quinoxaline(10) with m-trifluoromethylbenzenediazonium chloride gave 3-[α-(m-tri-fluoromethylphenylhydrazono)methoxycarbonylmethyl]-2-oxo-1,2dihydroquinoxaline(1 1), whose reaction with hydrazine hydrate afforded 3-[α-(m-trifluoromethylphenylh-ydrazono)hydrazinocarbonylmethyl]-2-oxo-1,2-dihydroquinoxaline(12). The reaction of α-arylhydrazonoacylhydrazide 12 with nitrous acid resulted in the Curtius re-arrangement to give 1-(m-trifluoromethylphenyl)-3-(3-oxo-3,4-dihydroquinoxalin-2- yl)-4,5-dihydro-lH-1,2,4-triazol-5-one(13) viα the α-arylhydrazonoacylazide(A). Attem-pts to isolation α-arylhydrazonoacylazide(A) was not successful, but it was found that the tautomerism of α-arylhydrazonoacylazide(A) between the hydrazone imine and diazenyl enamine forms in the solid state was investigated on the basis of the azide group determined by the IR spectrum.
새로운 3-Amino-1-aryl-lH-pyrazlo[3,4-b]quinoxaline의 합성
鄭周怜,李盛旭,金銀娥,韓盛旭,倉澤嘉久,金浩植 대구효성가톨릭대학교 자연과학연구소 1996 基礎科學硏究論集 Vol.10 No.-
The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydro-quinoxaline(13) with p-nitrobenzenediazonium chloride gave 3-[α-(p-nitrophenylhy-drazono)methoxycarbonylmethyl]-2-oxo-1,2-dihydroquinoxaline(14). The chlorina-tion of the α-arythydrazonoquinoxaline 14 with phosphoryl chloride provided 3-[α- (p -nitrophenylhydrazono)methoxycarbonylmethyll-2chloroquinoxaline(15), whose reaction with hydrazine hydrate afforded 3-hydrazinocarbonyl-1-(p-nitrophenyl)-1H-pyrazolo[3,4-blquinoxaline(16). The reaction of compound 16 with nitrous acid resulted in the Curtius rearrangement to give 3-amino-1-(p-nitrophenyl)-1H-pyrazo-lo(3,4-b)quinoxaline(17). The tautomeric behavior of 3-[α-(p-nitrophenylhydrano-no)methoxycarbonylmethyll-2-chloroquinoxaline(15) between the hydrazone imine and djazenylenarnine forms in the dimethyl sufoxide solution was investigated on the basis of the tautomer ratio determined by the 1H-NMR spectral data. The tautomer ratio of the hydrazone imine form versus the diazenylenarnine form in the compound 15 was 2 : 1.
새로운 1,2,4-Triazole 유도체의 합성에 관한 연구
金浩植,朴胎晝,都理香,李萬佶,倉澤嘉久 대구효성가톨릭대학교 자연과학연구소 1992 基礎科學硏究論集 Vol.1992 No.1
o-페닐렌디아민(3)을 출발물질로 하여 4단계를 거쳐 α-arylhydrazonoacylazide(7)를 합성하였다. 얻어진 α-arylhydrazonoacylazide(7) 디메틸슬폭시드 용액에서 hydrazone imine형과 diazenyl enamine 형으로 존재하는데 이들 사이의 토오토메리 현상을 ^1H-NMR 스펙트럼 데이터에 의하여 측정된 토오토머비로서 고찰하였다. α-Arylhydrazonoacylazide(7)를 벤젠용매에서 환류시켜 1-aryl-3-quinoxalinyl-1,2,4-triazole(8)을 합성하였다. α-Arylhydrazonoacylazide(7) was synthesized starting from o-phenylenediamine(3) in four steps. The tautomeric behavior of α-arylhydrazonoacylazide(7) between the hydrazone imine and diazenyl enamine forms in the dimethyl sulfoxide solution was investigated on the basis of the tautomer raio determined by the ^1H-NMR spectral data. The 1-aryl-3-quinoxalinyl-1,2,4-triazol(8) was synthesized from α-arylhydrazonoacylazide(7) by refluxing in benzene.
새로운 Quinoxalin-2-ylhydrazone類의 合成
郭美玉,鄭謚朱,金恩娥,金盛植,金銅恩,金浩植,倉澤嘉久 대구효성가톨릭대학교 자연과학연구소 1995 基礎科學硏究論集 Vol.9 No.-
The reaction of 2,6-djchloroquinoxaline(9) with m-chloroperbenzoic acid gave 2,6-dichloroquinoxaline 4-oxide(10), whose reaction with hydrazine hydrate provided 6-chloro-2-hydrazinoquinoxaline 4-oxide(11). Condensation of 6-chloro-2-hydrazinoquinoxaline 4-onide with substituted benzaldehydes or ketones to yieldsubstituted benzaldehyde quinoxalin-2-ylhydrazones(12a~c) or ketone quinoxalin-2-ylhydrazones(12d~f)was investigated. The structures of the synthesized com-pounds were confirmed on the basis of ir, 1H-nmr and mass spectral data,
2-Hydroxy-7(or 8)-methoxyphenazine-5,10-dioxide 의 合成
金浩植,金恩慶,金眞嬉,鄭謚朱,李萬佶,韓盛旭,倉澤嘉久 대구효성가톨릭대학교 자연과학연구소 1995 基礎科學硏究論集 Vol.9 No.-
2-Hydroxy-7(or 8)-methoxyphenazine-5,10-dioxide(13) was synthesizedby the reaction of hydroquinone with 5(or 6)-methoxybenzofuroxan(12) which had been obtained from p-anisidine. The structures of the synthesized compounds were confirmed on the basis of ir, 1H-nmr and elemental analysis. A possible mechan-ism for the formation of phenazine ring is discussed.
2-Hydroxy-7(or 8)-nitrophenazine-5,10-dioxide의 合成과 抗菌性
金浩植,鄭謚朱,金東一,鄭克,韓盛旭,倉澤嘉久 대구효성가톨릭대학교 자연과학연구소 1996 基礎科學硏究論集 Vol.10 No.-
2-Hydroxy-7(or 8)-nitrophenazine-5,10-dioxide(14) was synthesized by the reaction of hydroquinone with 5(or 6)-nitrobenzofuroxan(13) which had been obtained from 4-nitroaniline. And 2-hydroxyphenazine-5,10-dioxide(16) was prepared by the reaction of hydroquinone with benzofuroxan(15). The antibacterial activities of these phenazine dioxides were investigated in terms of minimum in-hibitory concentration by the common twofold dilution technique. It was observed that the antibacterial activity of phenazine dioxide bearing electron releasing substituent was stronger that of bearing electron withdrawing substituent.
Terazoloquinoxaline類의 간편한 合成에 관한 硏究
南順花,郭美玉,鄭周怜,韓盛旭,李萬佶,倉澤가久,金浩植 대구효성가톨릭대학교 자연과학연구소 1992 基礎科學硏究論集 Vol.6 No.-
The reaction of o-phenylenediamine with methyl pyruvate gave 3-methyl-2-oxo-1,2-dihydroquinoxaline, whose reaction with phosphoryl chloride afforded 2-ch-loro -3- methylquinoxaline . The reaction of 2- chloro-3- methylquinoxaline with sodium azide in dimethyl sulfoxide provided 4-rnothyltetrazolo(1,5-a)quinoxaline. The reac-tion of 2-chloro-3-methylquinoxaline with m-chloroperbenzoic acid gave 2-chloro-3-methylquinoxaline 4-oxide, whose reaction with sodium azide in dimethyl sulfoxide provided 4-mothyltetrazolo(1,5-a)quinoxaline 5-oxide. The tautomeric behavior of compound 15 and 17 between the azido and tetrazolo forms in a solid and solution was investigated on the basis of the tautomer ratio determined by the 1H-NMR spectral data. The tautomer ratios of the azido form versus the tetrazolo form were 1 : 2 and1 . 4.