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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.
Synthesis of Mesoionic Triazolo[4,3-α]quinoxalines
Yoshihisa, Kurasawa,Tae, Kawano,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 1 or 6-chloro-2-(1-methylhydrazino)-quinoxaline 5 with phenyl isothiocyanate under reflux in N,N-dimethylformamide gave 7-choloro-3-methyl-1,2,4-triazolo[4,3-a]quinoxalin-3-ium-1-thioate 4, which was also obtained by refluxing of 6-chloro-2-[1-methyl-2-(N-phenylthiocarbamoyl)hydrazino]quinoxaline 4-oxide 2b or 6-chloro-2-[1-methyl-2-(N-phenylthiocarbamoyl)hydrazino]quinoxaline 6 in N,N-dimethylformamide.
Yoshihisa, Kurasawa,Kim, Ho Sik,Tae, Kawano,Ritsuko, Katoh,Atsushi, Takada,Yoshihisa, Okamoto 대구효성가톨릭대학교 자연과학연구소 1991 基礎科學硏究論集 Vol.1991 No.1
The reaction of the 1,2-diazepino[3,4-b]quinoxalines 2a,b or 3a,b with N-bromosuccinimide/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxalines 4a,b, respectively.
Yoshihisa, Kurasawa,Kim, Ho Sik,Ritsuko, Katoh,Tae, Kawano,Atsushi, Takada,Yoshihisa, Okamoto 대구효성가톨릭대학교 자연과학연구소 1991 基礎科學硏究論集 Vol.1991 No.1
The reaction of the hydrazones 5a-c with 2-chloroacrylonitrile produced the 1,2-diazepino[3,4-b]quinoxaline hydrochlorides 6a-c, which were transformed into the 5,6,7,13-tetrahydro-5,14-methano-16-oxo-1,5,6-benzoxadiazonino[3,4-b]quinoxalines 7a-c, respectively. The oxidation of 7a-c with diethyl azodicarboxylate afforded the 7,13-dihydro-5,14-methano-16-oxo-1,5,6-benzoxadiazonino[3,4-b]quinoxalines 8a-c, respectively. Compounds 7a-c and 8a-c were also obtained by a one-pot synthesis from 5a-c and 6a-c, respectively.
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.