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Kurasawa, Yoshihisa,Kureyama, Tomomi,Yoshishiba, Noriko,Kathoh, Ritsuko,Takada, Atsushi,Kim, Ho Sik,Okamoto, Yoshihisa 대구효성가톨릭대학교 자연과학연구소 1993 基礎科學硏究論集 Vol.1993 No.1
The reaction of 6-chloro-2-(l-methylhydrazino)quinoxaline 4-oxide 8 with furfural, 3-methyl-2-thiophene-carbaldehyde, 2-pyrrolecarbaldehyde, 4-pyridinecarbaldehyde and pyridoxal hydrochloride gave 6-chloro-2-[2-(2-furylmethylene)-l-methylhydrazino]quinoxaline 4-oxide 5a, 6-chloro-2-[1-methyl-2-(3-methyl-2-thienyl-methylene)hydrazino]quinoxaline 4-oxide 5b, 6-chloro-2-[1-methyl-2-(2-pyrrolylmethylene)hydrazino]quinoxaline 4-oxide 5c, 6-chloro-2-[1-methyl-2-(4-pyridylmethylene)hydrazino]qunoxaline 4-oxide 5d and 6-chloro-2-[2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridylmethylene)-1-methylhydrazino]quinoxaline 4-oxide 5e, respectively. The reaction of compound 5a or 5b with 2-chloroacrylonitrile afforded 8-chloro-3-(2-furyl)-4-hydroxy-1-methyl-2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline-5-carbonitrile 6b, respectively, while the reaction of compound 5e with 2-chloroacrylonitrile furnished 11-chloro-7,13-dihydro-4-hydroxy-methyl-5,14-methano-1,7-dimethyl-16-oxopyrido[3',4':9,8][1,5,6]oxadiazonino[3,4-b]quinoxaline 7.
Kurasawa, Yoshihisa,Kureyama, Tomomi,Yoshishiba, Noriko,Okano, Tomoko,Takada, Atsushi,Kim, Ho Sik,Okamoto, Yoshihisa 대구효성가톨릭대학교 자연과학연구소 1993 基礎科學硏究論集 Vol.1993 No.1
The reaction of 7-chlorotetrazolo[1,5-a]quinoxaline 50oxide 4a or 7-chloro-1,2,4-triazolo[4,3-a]quinoxaline 5-oxide 4b with 2-chloroacrylonitrile gave 7-chloro-4-(2-cyano-2-hydroxyvinyl)tetrazole[1,5-a]quinoxaline 5a or 7-chloro-4-(2-cyano-2-hydroxyvinyl)-1,2,4-triazolo[4,3-a]uinoxaline 5b, respectively. Alcoholysis of com-pound 5a or 5b afforded 7-chloro-4-ethoxycarbonylmethylene-4,5-dihydrotetrazolo[1,5-a]quinoxaline 6a or 7-chloro-4-ethoxycarbonylmethylene-4,5-dihydro-1.2.4-triazolo[4,3-a]quinoxaline 6b, respectively. Compounds 5a,b were found to exist as a syn and anti mixture of the enol form, while compounds 6a,b occurred as the enamine and methylene imine forms. The tautomeric character and/or D-H exchange of the vinyl protons are described for compounds 5a,b and 6a,b.
Yoshihisa, Kurasawa,Noriko, Yoshishiba,Tomomi, Kureyama,Tomoko, Okano,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 5 with thriethyl orthoformate gave 7-chloro-1,2,4-triazolo[4,3-a]quinoxaline 5-oxide 6. The reaction of compound 6 with phenyl isocyanate afforded 7-chloro-4-phenylamino-1,2,4-triazolo[4,3-a]quinoxaline 7, while the reaction of compound 6 with phenyl isothiocyanate resulted in deoxygenation to provide 7-chloro-1,2,4-triazolo[4,3-a]quinoxaline 8. However, the reaction of compound 6 with allyl isothiocyanate effected the 1,3-dipolar cycloaddition reaction, but not deoxygenation, to furnish 9-chloro-4,5-dihydroisoxazolo[2,3-a][1,2,4]triazolo[3,4-c]quinoxaline-5-ylmethylisothiocyanate 9. Moreover, the reduction of compound 9 with iron/acetic acid resulted in ring transformation to give 11-chloro-7-hydroxy-4-thioxo-4,5,6,7,8,9-hexahydro-1,2,4-triazolo[4,3,2-o,p][1,3]diazocino[4,5-b]quinoxaline 10, whose acetylation afforded 5-acetyl-11-chloro-7-hydroxy-4-thioxo-4,5,6,7,8,9-hexahydro-1,2,4-triazolo[4,3,2-o,p][1,3]diazocino[4,5-b]quinoxaline 11.
Reaction of Enol Type Acyl Cyanide with o-Aminophenol
Kurasawa, Yoshihisa,Yoshishiba, Noriko,Kureyama, Tomomi,Takada, Atsushi,Kim, Ho Sik,Okamoto, Yoshihisa 대구효성가톨릭대학교 자연과학연구소 1993 基礎科學硏究論集 Vol.1993 No.1
The reaction of 7-chloro-4-(2-cyano-2-hydroxyvinyl)tetrazolo[1,5-a]quinoxaline 2a with o-aminophenol gave 7-chloro-4-(b-hydroxyphenylcarbamoylmethylene)-4,5-dihydrotetrazolo[1,5-a]quinoxaline 4, while the reaction of compound 2a with o-aminophenol hydrochloride afforded 4-[2-(2benzoxazolyl)-2-hydroxyvinyl]-7-chloro-tetrazolo[1,5-a]quinoxaline 5, whose acetylation provided 4-[2-acetoxy-2-(2-benezoxazolyl)vinyl]-7-chlorotetra-zolo[1,5-a]quinoxaline 6. The behavior in a deuteriodimethyl sulfoxide or deuteriotrifluoroacetic acid solu-tion is described for compounds 4-6.
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.