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Yoshihisa, Kurasawa,Ritsuko, Katoh,Atsushi, Takada,Kim, Ho Sik,Yoshihisa, Okamoto 대구효성가톨릭대학교 자연과학연구소 1992 基礎科學硏究論集 Vol.1992 No.1
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 4a with methyl or phenyl isothiocyanate gave 6-chloro-2-[1-methyl-2-(N-methylthiocarbamoyl)hydrazino]quinoxaline 4-oxide 7a or 6-chloro-2-[1-methyl-2-(N-phenylthiocarbamoyl)hydrazino]quinoxaline 4-oxide 7b, respectively, whose reaction with dimethyl acetylenedicarboxylate afforded 6-chloro-2-[N-methyl-N-(5-methoxycarbonylmethylene-3-methyl-4-oxo-2-thioxoimidazolidin-l-yl)]aminoquinoxaline 4-oxide 8a or 6-chloro-2-[N-methyl-N-(5-methoxycarbonylmethylene-4-oxo-3-phenyl-2-thioxoimidazolidin-l-yl)]aminoquinoxaline 4-oxide 8b, respectively.
Reaction of 2-(5-Aminopyrazol-1-yl) quinoxaline 4-Oxides with Dimethyl Acetylenedicarboxylate
Yoshihisa, Kurasawa,Ritsuko, Katoh,Fumiko, Mori,Minori, Fukuchi,Megumi, Okamoto,Atsushi, Takada,Kim, Ho Sik,Yoshihisa, Okamoto 대구효성가톨릭대학교 자연과학연구소 1992 基礎科學硏究論集 Vol.1992 No.1
The reaction of 6-chloro-2-hydrazinoquinoxaline 4-oxide 6 with ethyl 2-(ethoxymethylene)-2-cyanoacetate or (1-ethoxyethylidene)malononitrile gave 2-(5-amino-4-ethoxycarbonylpyrazol-l-yl)-6-chloroquinoxaline 4-oxide 7a or 2-(5-amino-4-cyano-3-methylpyrazol-l-yl)-6-chloroquinoxaline 4-oxide 7b, respectively. The reaction of compound 7a or 7b with dimethyl acetylenedicarboxylate resulted in the 1,3-dipolar cycloaddition reaction and then ring transformation to afford 4-(5-amino-4-ethoxycarbonylpyrazol-l-yl)-8-chloro-1,2,3-trismethoxycarbonylpyrrolo[1, 2-a]quinoxaline 8a or 4-(5-amino-4-cyano-3-methylpyrazol-l-yl)-8-chloro-1,2,3-trismethoxycarbonylpyrrolo[1,2-a]quinoxaline 8b, respectively.
A New Type of Deoxygenation of Quinoxaline N-Oxides
Yoshihisa, Kurasawa,Ritsuko, Katoh,Tomomi, Kureyama,Noriko, Yoshishiba,Atsushi, Takada,Kim, Ho Sik,Yoshihisa, Okamoto 대구효성가톨릭대학교 자연과학연구소 1992 基礎科學硏究論集 Vol.1992 No.1
The reaction of 6-chloro-2-[2-(p-chlorobenzylidene)-1-methylhydrazino]quinoxaline 4-oxide 3a or 2-[2-(p-bromobenzylidene)-1-methylhydrazino]-6-chloroquinoxaline 4-oxide 3b with dimethyl acetylenedicarboxylate under reflux in N,N-dimethylformamide resulted in deoxygenation to give 6-chloro-2-[2-(p-chlorobenzylidene)-1-methylhydrazino]quinoxaline 4a or 2-[2-(p-bromobenzilidene)-1-methylhydrazino]-6-chloroquinoxaline 4b, respectively, while the reaction of compound 3a or 3b with dimethyl acetylenedicarboxylate under reflux in dioxane precipitated dimethyl 8-chloro-4-[2-(p-chlorobenzyli-dene)-1-methylhydrazino]-3aH-isoxazolo[2,3-a]quinoxaline-2,3-dicarboxylate 6a or dimethyl 4-[2-(p-bromobenzylidene)-1-methylhydrazino]-8-chloro-3aH-isoxazolo[2,3-a]quinoxaline-2,3-dicarboxylate 6b, respectively. Further refluxing of compound 6a or 6b in N,N-dimethylformamide provided compound 4a or 4b, respectively.