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1.
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
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.
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
4.
Ho Sik Kim Yoshihisa Kurasawa Chiemi Yoshii Minako Masuyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1990,27(4):1111-1114
The pyridazino[3,4-b]quinoxalines 6a,b and pyrazolo[3,4-b]quinoxaline hydrochloride 9 were synthesized by the 1,3-dipolar cycloaddition reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 5 with dimethyl or diethyl acetylenedicarboxylate and 2-chloroacrylonitrile, respectively. The reaction mechanisms were postulated for the formation of 6a,b and 9 . 相似文献
5.
Yoshihisa Kurasawa Kaoru Yamazaki Setsuko Tajima Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(1):281-282
The reactions of 3-methyl-2-oxo-1,2-dihydroquinoxaline 3 with chlorophenyl diazonium salts afforded the hydrazones 4a-c , whose chlorinations with phosphoryl chloride gave the dichlorides 5a-c . Refluxing of the dichlorides 5a-c and base in N,N-dimethylformamide provided the 1-aryl-1H-pyrazolo[3,4-b]quinoxalines 6a-c . 相似文献
6.
The dihydropyridazine ring undergoes contraction to a dihydropyrrole ring to give 1-phenyl-2-benzylideneaminodihydropyrrolo[3,4-b]indol-3-ones when 1-phenyldihydropyridazino[4,5-b]indol-4-ones are treated with aromatic aldehydes under acid catalysis conditions. The reaction mechanism consists in the formation of a (3-indolyl)phenylmethyl cation, which leads to opening of the pyridazine ring and subsequent development of a bond between the carbonium center and the amide nitrogen atom.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1408, October, 1976. 相似文献
7.
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.
K. F. Turchin Yu. N. Sheinker T. V. Kartseva G. S. Predvoditeleva 《Chemistry of Heterocyclic Compounds》1984,20(11):1281-1286
On the basis of the spectral data (1H and 13C NMR, measurements of the nuclear Overhauser effect (NOE) and t1, UV spectra), the structure of tricyclic compounds formed in the condensation of substituted o-phenylenediamines with 3,4,6-trichloropyridazine, as well as two types of isomeric products of their alkylation, was established; tautomerism and protonation of the compounds obtained were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1549–1555, November, 1984. 相似文献
10.
Yoshihisa Kurasawa Muneto Muramatsu Kaoru Yamazaki Setsuko Tajima Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(3):959-960
The reaction of 3-(2,3-dihydro-4-methyl-3-thioxo-4H-1,2,4-triazol-5-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline 4 with o-chlorobenzenediazonium chloride gave 3-[α-(o-chlorophenylhydrazono)-2,3-dihydro-4-methyl-3-thioxo-4H-1,2,4-triazol-5-ylmethyl]-2-oxo-1,2-dihydroquinoxaline 6 , whose refluxing in phosphoryl chloride/pyridine afforded 1-(o-chlorophenyl)-3-(2,3-dihydro-4-methyl-3-thioxo-4H-1,2,4-triazol-5-yl)-1H-pyrazolo[3,4-b]quinoxaline 7. The reactions of 6 and 7 with nitrous acid resulted in sulfur extrusion to provide 1-(o-chlorophenyl)-3-(4-methyl-4H-1,2,4-triazol-5-yl)1H-pyrazolo[3,4-b]quinoxaline 8 and 3-[α-(o-chlorophenylhydrazono)-4-methyl-4H-1,2,4-triazol-5-ylraethyl]-2-oxo-1,2-dihydroquinoxaline 9 , respectively. 相似文献
11.
A. Monge Vega I. Aldana M. M. Rabbani E. Fernandez-Alvarez 《Journal of heterocyclic chemistry》1980,17(1):77-80
This paper describes the synthesis of the previously unknown 11H-1,2,4-triazolo[4,3-b]pyridazino[4,5-b]indoles (2) and 11H-tetrazolo[4,5-b]pyridazino[4,5-b]indoles (3) from 4-hydrazino-5H-pyridazino[4,5-b]indoles (1) , as well as the synthesis of 1,2,4-triazolo[3,4-f]-1,2,4-triazino-[4,5-a]indoles (10) from 2-indolecarbohydrazide (4) . Compounds 2 were obtained by acylation of compounds 1 , followed of thermal cyclization and compounds 3 by treating compounds 1 with nitrous acid. The reactions of compound 4 with formic acid or ethyl orthoformiate gave 1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indole (6) . Treating this last compound with phosphorus oxychloride or phosphorus pentasulfide, followed by hydrazine, gave 1-hydrazino-1,2,4-triazino-[4,5-a]indole (9) . Acylation of this last compound, followed of cyclization gave compounds 10 . All the compounds were characterized by elemental analysis and ir and 1H-nmr spectra. 相似文献
12.
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
13.
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
14.
Yoshihisa Kurasawa Muneto Muramatsu Kaoru Yamazaki Setsuko Tajima Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(5):1391-1394
The novel 1H-pyrazolo[3,4-b]quinoxalines (flavazoles) 9–15 were synthesized from 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline 6 via a convenient hydrazone synthesis, and these flavazoles were clarified to have the antifungal activity. 相似文献
15.
We report herein an original and rapid synthesis of substituted 2-tosyl-1,2,3,4-tetrahydropyrido[3,4-b]quinoxaline derivatives by TDAE strategy from 2,3-bis(bromomethyl)quinoxaline and N-(toluenesulfonyl)benzylimines. 相似文献
16.
He Yunhe Wang Hongxue Gao Tingyu Liu Jia Jiang Wenting Zhang Hong 《Research on Chemical Intermediates》2021,47(6):2231-2243
Research on Chemical Intermediates - In this work, a simple and convenient synthesis of a new series of benzo[h]quinoline-based α-arylidene cycloketone derivatives, namely... 相似文献
17.
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
18.
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
19.
4-Amino-5-ethyl-4H-1,2,4-triazole-3-thiol was used as a key intermediate for the synthesis of triazolo[3,4-b][1,3,4]thiadiazines, triazolo[4,3-b][1,2,4,5]tetrazines and Schiff’s base via reactions with various hydrazonoyl halides and salicyaldehyde, respectively. Moreover triazolyl-N-N′-triazole derivatives were prepared from reaction of Schiff’s base with various hydrazonoyl halides. The structures of all the newly synthesized heterocyclic compounds were established by considering elemental analysis and spectral data. 相似文献
20.
A. Poursattar Marjani J. Khalafy R. H. Prager 《Chemistry of Heterocyclic Compounds》2012,48(6):931-935
Several new derivatives of imidazo[1,2-a]quinoxalines have been synthesized in good to excellent yields starting from arylaminoisoxazol-5(2H)-ones and 2,3-dichloroquinoxaline through a rearrangement under mild base-catalyzed conditions. 相似文献