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1.
Yoshihisa Kurasawa Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1993,30(6):1659-1661
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 1 with ethyl 2-ethoxymethylene-2-cyano-acetate or ethoxymethylenemalononitrile gave 6-chloro-2-[2-(2-cyano-2-ethoxycarbonylvinyl)-1-methylhy-drazino]quinoxaline 4-oxide 3a or 6-chloro-2-[2-(2,2-dicyanovinyl)-1-methylhydrazino]quinoxaline 3b , respectively. The reaction of 3a with a base afforded 7-chloro-1-methyl-1,5-dihydropyridazino[3,4-b]quinoxaline 4 . From the NOE spectral data, the 1-methyldihydropyridazino[3,4-b]quinoxalines 2a, 2b and 4 were found to exist as the 1,5-dihydro form in a dimethyl sulfoxide or trifluoroacetic acid/dimethyl sulfoxide solution. 相似文献
2.
Ho Sik Kim Yoshihisa Kurasawa Atsushi Takada 《Journal of heterocyclic chemistry》1989,26(5):1511-1513
The reaction of 2,6-dichloroquinoxaline 4-oxide 4 with methylhydrazine gave 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 5, whose reaction with dimethyl acetylenedicarboxylate or 2-chloroacrylonitrile resulted in the 1,3-dipolar cycloaddition reaction to afford 7-chloro-3,4-bismethoxycarbonyl-1-methyl-1,2-dihydropyridazino[3,4-b]quinoxaline 6 or 6-chloro-3-hydroxymethylene-1-methyl-2,3-dihydro-1H-pyrazolo[3,4-b] quinoxaline hydrochloride 7, respectively. 相似文献
3.
The transient existence of thieno[3,4-b]quinoxaline ( 2d ) as a product of dehydration of 1,3-dihydrothieno[3,4-b]quinoxaline 2-oxide ( 5 ) was demonstrated by trapping experiments with N-phenylmaleimide and dimethyl acetylenedicarboxylate. Attempts to isolate 2d from reaction mixtures arising from dehydration of 5 and from dehydrogenation of 1,3-dihydro-thieno[3,4-b]quinoxaline ( 8 ) were unsuccessful. 相似文献
4.
Yoshihisa Kurasawa Tomomi Kureyama Noriko Yoshishiba Ritsuko Katoh Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1993,30(2):537-541
The reaction of 6-chloro-2-(1-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)-1-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]quinoxa-line 4-oxide 5c , 6-chloro-2-[1-methyl-2-(4-pyridylmethylene)hydrazino]quinoxaline 4-oxide 5d and 6-chloro-2-[2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridylmethylene)-1-methylhydrazino]quinoxalme 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 6a or 8-chloro-4-hydroxy-1-methyl-3-(3-methyl-2-thienyl)-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. 相似文献
5.
Ho Sik Kim Eun Kyoung Kim Sung Sik Kim Yong Tae Park Young Seuk Hong Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》1997,34(1):39-42
The pyridazino[3,4-b]quinoxaline 12 was synthesized by the cyclization of the α-arylhydrazonoacyl-hydrazide 11. The reaction of compound 12 with phosphoryl chloride gave pyridazino[3,4-b]quinoxaline 13, whose reactions with sodium azide or cyclic secondary amines provided pyridazino[3,4-b]quinoxalines 14,17 and 18, respectively. The acylhydrazide 15 was also cyclized to pyridazino[3,4-b]quinoxaline 16. 相似文献
6.
Yoshihisa Kurasawa Muneto Muramatsu Kaoru Yamazaki Setsuko Tajima Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(2):633-635
The chlorination of the α-hydrazonoester 4 with phosphoryl chloride/pyridine gave 3-[α-(o-chlorophenylhydrazono)methoxycarbonylmethyl]-2-chloroquinoxaline 5 , whose cyclization with 1,8-diazabicyclo[5,4,0]-7-undecene afforded 3-methoxycarbonyl-1-(o-chlorophenyl)-1H-pyrazolo[3,4-b]quinoxaline 6 . The reaction of 6 with hydrazine hydrate provided 3-hydrazinocarbonyl-1-(o-chlorophenyl)-1H-pyrazolo[3,4-b]quinoxaline 7 , whose reactions with methyl and allyl isothiocyanates furnished 3-(2,3-dihydro-4-methyl-3-thioxo-4H-1,2,4-triazol-5-yl)-1-(o-chlorophenyl)-1H-pyrazolo[3,4-b]quinoxaline 2 and 3-(4-allyl-2,3-dihydro-3-thioxo-4H-1,2,4-triazol-5-yl)-1-(o-chloropheny)-1H-pyrazolo[3,4-b]quinoxaline 8 , respectively. Moreover, the reactions of 7 with triethyl orthoformate and orthoacetate gave 1-(o-chlorophenyl)-3-(1,3,4-oxadiazol-5-yl)-1H-pyrazolo-[3,4-b]quinoxaline 9a and 1(o-chlorophenyl)-3-(2-methyl-1,3,4-oxadiazol-5-yl)-1H-pyrazolo[3,4-b]quinoxaline 9b , respectively. 相似文献
7.
The o-diamine, 3,4-diamino-1,2,5-thiadiazole ( 2 ), was synthesized from 3,4-dichloro-1,2,5-thiadiazole ( 3 ) hy three methods. Aqueous glyoxal cyclized 2 into [1,2,5]thiadiazolo[3,4–6]-pyrazine ( 14 ). 3,4-Dichloro-1,2,5-thiadiazole 1,1-dioxide ( 18 ) reaeted with 2 to give 1,3-dihydro-bis[1,2,5]thiadiazolo[3,4-b:3′,4′-e]pyrazine 2,2-dioxide ( 19 ). The reaction of 2 with selenium oxyehloride led to [1,2,5]selenadiazolo[3,4-c] [1,2,5]thiadiazole ( 12 ). Ring closure of 2,3-diaminoquinoxaline ( 4 ) with thionyl chloride or selenium oxychloride gave [1,2,5]thiadiazolo-[3,4-b]quinoxaline ( 21 ) and [1,2,5]selenadiazolo[3,4-b]quinoxaline ( 22 ), respectively. Sulfurous acid reduced 21 to the 4,9-dihydro derivative 23 , which was reoxidized to 21 with chloranil. Aqueous hase hydrolyzed 21 to 4 via the hydrated intermediate 24 . Aqueous glyoxal cyclized 4 to the covalent hydrate of pyrazino[2,3-b]quinoxaline ( 26 ), 27 , which was dehydrated to 26 . Compound 26 underwent rapid addition of two alcohols in a process analogous to covalent hydration. 相似文献
8.
A facile synthesis of novel 1,2-diazepino[3,4-b]quinoxalines by a 1,3-dipolar cycloaddition reaction
Ho Sik Kim Yoshihisa Kurasawa Chiemi Yoshii Minako Masuyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1990,27(3):819-822
The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxides 4a,b with 2-chloroacrylonitrile gave the 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxalines 5a,b , respectively, which were converted into the 2,3,4,6-tetrahydro-1H-1,2-diazepino[3,4-b]quinoxalines 7a,b and 8a,b , respectively. 相似文献
9.
Maria S. Vrettou John K. Gallos Demetrios N. Nicolaides 《Journal of heterocyclic chemistry》1988,25(3):813-814
Pyrazino[2,3-b]quinoxaline 1,4-dioxides 3a-e were prepared by reacting Furoxano[3,4-b]quinoxaline with alkynes and alkenes. 相似文献
10.
Joseph Armand Yvette Armand Line Boulares Christian Bellec Jean Pinson 《Journal of heterocyclic chemistry》1985,22(6):1519-1525
The reaction of o-phenylenediamine with a β-ketoacid, leads in most cases to quinoxalinones. Their structure has been determined as well as that of their corresponding hydrazones. The reaction of hydrazine with these quinoxalinones gives dihydropyridazino[3,4-b]quinoxalines, the structure of which has been ascertained. It has been shown that among the six possible formulas, the only 1,2-dihydro structure fits with the spectroscopic data. On the contrary, N-substituted o-phenylenediamines lead to 2,10-dihydro derivatives. The electrochemical behavior of the 2,10-dihydro-10-methyl-3-phenylpyridazino[3,4-b]quinoxaline has been investigated. It has also been shown that the 3,4,6-trichloropyridazine reacts with o-phenylenediamines to give 5,10-dihydropyridazino[3,4-b]quinoxalines. These compounds can be oxidized to give the new heterocycle pyridazino[3,4-b]quinoxaline. 相似文献
11.
Yoshihisa Kurasawa Harumi Arai Kiyoko Arai Atsushi Satoh Satoyuki Ninomiya Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(4):1219-1220
Novel 4-chlorophenylhydrazono-3-oxo-1,2,3,4-tetrahydropyridazino[3,4-b]quinoxalines 10a-c were synthesized by the cyclization of the α-hydrazonohydrazides 8a-c. The chlorination of 10a with phosphoryl chloride afforded 3-chloro-4-[2-(o-chlorophenyl)hydrazino]pyridazino[3,4-b]quinoxaline 12. 相似文献
12.
Yoshihisa Kurasawa Noriko Yoshishiba Tomomi Kureyama Tomoko Okano Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1992,29(6):1653-1656
The reaction of 6-chloro-2-hydrazinoquinoxaline 4-oxide 5 with triethyl 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]quinoxalin-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. 相似文献
13.
Yoshihisa Kurasawa Ho Sik Kim Tae Kawano Ritsuko Katoh Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1991,28(1):199-201
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. 相似文献
14.
Yoshihisa Kurasawa Ho Sik Kim Ritsuko Katoh Tae Kawano Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1991,28(3):787-792
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. 相似文献
15.
Starting from the readily available 2-methyl-3-benzoylfuran, 1-phenylthieno[3,4-b]furan and 1-phenyl-seleno[3,4-b]furan were prepared. Also, starting from phenyl 3-methylindol-2-yl ketone and aryl 2-methyl-indole-3-yl ketones a series of substituted thieno[3,4-b]indoles and substituted seleno[3,4-b]indoles were prepared. 相似文献
16.
George Bobowski 《Journal of heterocyclic chemistry》1987,24(2):473-479
Treatment of 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1-methylcyclohexanol ( 2a ) with acetic anhydride or methyl isocyanate gave 2-acetyl-2,3,4,9-tetrahydro-1-(6-oxoheptylidene)-1H-pyrido[3,4-b]indole ( 3 ) or 1,3,4,9-tetrahydro-N-methyl-1-(6-oxoheptylidene)-2H-pyrido[3,4-b]indole-2-carboxamide ( 4 ), respectively. Simpler analogues, 1-alkyl-4,9-dihydro-3H-pyrido[3,4-b]indoles, 7 , subjected to identical reaction conditions, gave 2-acetyl-1-alkylidene-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles 8 and 1,3,4,9-tetrahydro-N-methyl-1-alkyli-dene-2H-pyrido[3,4-b]indole-2-carboxamides 9 , respectively. A limited lanthanide shift reagent study to determine stereochemical assignments was also performed. 相似文献
17.
Yoshihisa Kurasawa Akiko Takano Kyoko Kato Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1996,33(3):757-762
The reaction of 6-chloro-2-(l-methylhydrazino)quinoxaline 1-oxide 3 with acetylenedicarboxylates gave the 8-chloro-1-memyl-1,5-dihydropyridazino[3,4-b]quinoxaline-3,4-dicarboxylates 4a,b and 2-(pyrazol-4-yl)quinoxaline 1-oxides 5a,b . The formation of compounds 4a,b would follow the 1,3-dipolar cycloaddition reaction, subsequent 1,2-hydrazino migration, and then dehydrative cyclization, while the production of compounds 5a,b would proceed via the addition of the hydrazino group to acetylene-dicarboxylate leading to the construction of a pyrazole ring, followed by rearrangement of the pyrazole ring. Compounds 5a,b were deoxidized with phosphoryl chloride/N,N-dimethylformamide to change into the 4-(quinoxalin-2-yl)pyrazole-3-carboxylates 8a,b . 相似文献
18.
The synthesis of some pyrido[3,4-b]pyrano[3,4-b]indoles ( 3 ) from 3-hydroxy-4-(3-indolyl)piperidines ( 6 ) is reported. 相似文献
19.
Starting from the readily available aryl 3-methyl-2-benzo[b] furyl ketones a series of 3-sub-stituted thieno[3,4-b] benzofurans and 3-substituted selenolo[3,4-b] benzofurans were prepared in high yield. The parent compound, thieno[3,4-b] benzofuran was prepared through the reaction of thioacetamide with 2-chloromethyl-3-formylbenzo[b] furan in moderate yield. 相似文献
20.
Ho Sik Kim Eun Ah Kim Geuk Jeong Yong Tae Park Young Seuk Hong Yoshihisa Okamoto Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》1998,35(2):445-450
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 8 with acetic anhydride resulted in the intramolecular cyclization to give 8-chloro-2,4-dimethyl-4H-1,3,4-oxadiazino[5,6-b]quinoxaline 7a , while the reaction of compound 8 with acetic anhydride/pyridine or acetic anhydride/acetic acid afforded 3-(2,2-diacetyl-1-memymydrazmo)-7-chloro-2-oxo-1,2-dihydroquinoxaline 9 , effecting no intramolecular cyclization. The reaction of 2-(2-acetyl-1-methylhydrazino)-6-chloroquinoxaline 4-oxide 10a or 6-chloro-2-(1-methyl-2-trifluoroacetylhydrazino)quinoxaline 4-oxide 10b with phosphoryl chloride provided compound 7a or 8-chloro-4-memyl-2-trifluoromethyl-4H-1,3,4-oxadiazino[5,6-b]quinoxaline 7b , respectively. The reaction of compound 7b with phosphorus pentasulfide gave 7-chloro-3-(1-methyl-2-trifluoroacetylhydrazino)-2-thioxo-1,2-dihydroquinoxaline 11 , whose dehydration with sulfuric acid in acetic acid afforded 8-chloro-4-methyl-2-trifluoromemyl-4H-1,3,4-thiadiazino[5,6-b]quinoxaline 12 . 相似文献