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1.
Yoshihisa Kurasawa Muneto Muramatsu Kaoru Yamazaki Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(5):1387-1390
The reactions of 3-(α-chlorophenylhydrazono)hydrazinocarbonylmethyl-2-oxo-1,2-dihydroquinoxalines 4a,c with triethyl orthoesters resulted in the intramolecular cyclization to give the 3-(α-chlorophenylhydrazono-1,3,4-oxadiazol-2-ylmethyl)-2-oxo-1,2-dihydroquinoxalines 5a-d , but not the 1,2,4,5-tetrazepinylquinoxalines 6a-d . The cyclization mode into the 1,3,4-oxadiazole ring was confirmed by the alternate syntheses of 5a,c from the reactions of the 3-(1,3,4-oxadiazol-2-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxalines 7a,b with o-chlorobenzenediazonium chloride. Moreover, the reactions of 3-(benzimidazol-2-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline hydrochloride 8 with o-, m- and p-chlorobenzenediazonium chlorides afforded the 3-(α-chlorophenylhydrazonobenzimidazol-2-ylmethy])-2-oxo-1,2-dihydroquinoxa]ine hydrochlorides 9a-c , respectively. Compounds 5a-d and 9a-c were found to exhibit antimicrobial activities. 相似文献
2.
Yoshihisa Kurasawa Muneto Muramatsu Kaoru Yamazaki Setsuko Tajima Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1986,23(4):1245-1248
3-(α-Chlorophenylhydrazono-1,3,4-oxadiazol-2-ylmethyl)-2-oxo-1,2-dihydroquinoxalines 4a-d and 3-(α-chlorophenylhydrazono)methoxycarbonylmethyl-2-oxo-1,2-dihydroquinoxalines 5a-c have been clarified to exhibit the characteristic tautomeric equilibria between the hydrazone imine form C and the diazenyl enamine form D with a long-range prototropy by means of the pmr and 13C-nmr spectroscopies. 相似文献
3.
Yoshihisa Kurasawa Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1985,22(6):1715-1718
The reaction of the hydrazone 3a with hydrazine hydrate in DBU/ethanol conveniently gave 3-(4-amino-5-methyl-4H-1,2,4-triazol-3-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline 6 . The reactions of 6 with an equimolar and 2-fold molar amount of nitrous acid afforded 3-(α-hydroxyimino-4-amino-5-methyl-4H-1,2,4-triazol-3-ylmethyl)-2-oxo-1,2-dihydroquinoxaline 9 and 3-(α-hydroxyimino-5-methyl-2H-1,2,4-triazol-3-ylmethyl)-2-oxo-1,2-dihydroquinoxaline 10 , respectively, which were converted into the 3-heteroarylisoxazolo[4,5-b]quin-oxalines 13a,b and 11 , respectively. Compound 9 was also cyclized into the 8-quinoxalinyl-1,2,4-triazolo-[3,4-f][1,2,4]triazines 14a,b . 相似文献
4.
Yoshihisa Kurasawa Akiko Takano Kyoko Kato Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1996,33(2):421-425
The o-substituted 3-(arylhydrazono)methyl-2-oxo-1,2-dihydroquinoxalines 1a-c and 2a , c were synthesized to investigate the tautomeric behavior between the hydrazone imine A and diazenylenamine B forms in a series of mixed dimethyl sulfoxide/trifluoroacetic acid media. The chemical shifts of the hydrazone NH, N4-H, hydrazone CH, and diazenyl CH protons for o-, m-, and p-substituted 3-(arylhydrazono)methyl-2-oxo-1,2-dihydroquinoxalines 1 and 2 synthesized so far are summarized in Tables 3 and 4, respectively, which are found to be useful for the specification of the proton signals due to the hydrazone imine form A (hydrazone NH, hydrazone CH) and diazenylenamine form B (N4-H, diazenyl CH). 相似文献
5.
将1,3,4-噁二唑基团引入二芳基乙烯分子中, 合成了2种新的二芳基乙烯类光致变色化合物1-氰基-2-(2H-5-苯基-1,3,4-噁二唑)-1,2-二(2,4,5-三甲基-3-噻吩)乙烯(3)和1,4-二{[1-氰基-2-(2H-5-苯基-1,3,4-噁二唑)-1,2-二(2,4,5-三甲基-3-噻吩)乙烯]-1,3,4-噁二唑}苯(4). 通过IR, NMR, MS和元素分析对化合物进行了结构表征, 并研究了其UV-Vis吸收、荧光发射、动力学特性和抗疲劳性质. 实验结果表明, 化合物[STHZ]3[STBZ]和[STHZ]4[STBZ]具有良好的光致变色性质, 光致变色闭环反应为零级反应, 开环反应为一级反应. 相似文献
6.
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
7.
New 3-acylamino-2-oxazolidinone derivatives 3 were obtained in good yields by reaction of 5-aryl (or benzyl)3-(2-hydroxyethyl)1,3,4-oxadiazol-2(3H)ones 1 with sodium ethylate. Treatment of ethyl 5-aryl-2-oxo-1,3,4-oxadiazole-3(2H)-acetates 7 with aromatic aldehydes in the presence of sodium ethylate or sodium hydride afforded 3-acylamino-5-aryl-4-ethoxycarbonyl-2-oxazolidinone derivatives as two trans- 5 and cis- 6 racemics. Only RS,SR-racemates were obtained with acetophenone under the same conditions. 相似文献
8.
A convenient method has been developed for the synthesis of 3-alkanoyl-and 3-benzoyl-2-oxo-1,2-dihydroquinoxalines from the
corresponding 3-(α-azidoalkyl)quinoxalines using acetic acid.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 574–577, 2007. 相似文献
9.
Conclusions The reaction of dialkylamides of 3-phenyl-3-chloro-2-oxopropionic acid with orthophenylenediamine gave 2-(N,N-dialkylcarbamoyl)-1,4-dihydroquinoxalines, while esters of this acid react with ortho-phenylenediamine to give 3-(-chlorobenzyl)-2-oxo-1,2-dihydro-quinoxalines, which react with phosphites to yield the corresponding 3-(O,O-dialkylphos-phonobenzyl)-2-oxo-1,2-dihydroquinoxalines.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1412–1414, June, 1989. 相似文献
10.
O. A. Komarova N. M. Igidov A. E. Rubtsov V. V. Zalesov A. S. Makarov Yu. S. Toksarova 《Russian Journal of Organic Chemistry》2010,46(2):236-240
Reactions of 1,2-diphenylethane-1,2-dione hydrazone with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic
acids provided 4-aryl-4-oxo-2-[2-(2-oxo-1,2-diphenylethylidene) hydrazino]but-2-enoic and 5,5-dimethyl-4-oxo-2-[2-(2-oxo-1,2-diphenylethylidene)hydrazino]hex-2-enoic
acids. The acids derivatives can exist in solutions as Z- and β-enehydrazino-or β-ketohydrazone forms, and under the treatment with acetic anhydride they undergo cyclization into
5-aryl- and 5-tert-butyl-3-[2-(2-oxo-1,2-diphenylethylidene)hydrazono]-2,3-furandiones. 相似文献
11.
5-(N-Methoxy-N-methyl)amino-3-aryl-1,3,4-oxadiazol-2(3H)-ones 3 undergo a heteroretro-ene reaction in refluxing methanol in which the leaving enophile is formaldehyde. The resulting 5-(methylimino)-3-aryl-1,3,4-oxadiazolidin-2-one 4 may be viewed as a kinetic product which tautomerizes to the more stable 5-(methylamino)-3-aryl-1,3,4-oxadiazol-2(3H)-one 5 as the thermodynamic product. Comparison of calculated reaction energies reveals that the presence of the heterocyclic ring facilitates the retro-ene reaction, but the expulsion of formaldehyde is predicted to be highly exothermic even in its absence. 相似文献
12.
Pascal Cauliez Daniel Couturier Benoît Rigo Dominique Fasseur Patrice Halama 《Journal of heterocyclic chemistry》1993,30(4):921-927
The condensation of pyroglutamic acids with 1,2-phenylenediamine leads to 2-(5-oxo-2-pyrrolidinyl)benzimidazoles and the cyclization of disilylated diacylhydrazines derived from the same acids gives 2-(5-oxo-2-pyrrolidinyl)-1,3,4-oxadiazoles. These compounds show weak antifungal activity. 相似文献
13.
为了选择性检测小分子生物硫醇,以具有优良荧光性能的喹啉酮为荧光团,依据依布硒啉中Se—N键易与硫醇分子反应的性质,将喹啉酮组块(E)-3-(5-巯基-1,3,4-恶二唑-2-基)-N-(4-甲基-2-氧代-1,2-二氢喹啉-7-基)丙烯酰胺(MQ5)与依布硒啉2-(4-溴苯基)苯并[d][1,2]硒唑-3(2H)-酮(SQ6)对接,设计合成了一种新型荧光探针(E)-N-(4-甲基-2-氧代-1,2-二氢喹啉-7-基)-3-(5-((4-(3-氧代苯并[d][1,2]硒烯唑-2 (3H)-基)苯基)硫基)-1,3,4-噁二唑-2-基)丙烯酰胺(MNQ)。 通过傅里叶变换红外光谱(FT-IR)、核磁共振波谱仪(NMR)和高分辨质谱(HRMS)和荧光光谱等测试手段对其进行了结构表征,探究了其荧光性能。 结果表明,MNQ对谷胱甘肽(GSH)有明显的荧光猝灭,在其他氨基酸等干扰时,探针具有良好的抗干扰能力,可作为识别检测GSH的荧光猝灭型探针。 检测限为2.99×10-8 mol/L,响应时间在35 s可完成,有望作为检测谷胱甘肽的荧光探针。 相似文献
14.
Ren Milcent Go Barbier Tatiana Tzirenstchikow Luc Lebreton 《Journal of heterocyclic chemistry》1989,26(1):231-236
Some 5-aryl-3-carbazoyl-1,3,4-oxadiazol-2(3H)-one derivatives 6 and 9 have been synthesized in two ways. The expected thermal ring transformation into 2,5-disubstituted 1,3,4-oxadiazoles did not occur but, by acid hydrolysis of 5-aryl-3-[3-benzylidene-2-methyl(or phenyl)carbazoyl]-1,3,4-oxadiazol-2(3H)-ones 6 , a new ring transformation took place and the corresponding 4-benzamido-1-methyl(or phenyl)-1,2,4-triazolidine-3,5-dione derivatives 11 were formed. The 4-amino-1-phenyl-1,2,4-triazolidine-3,5-dione ( 19 ) has been prepared and its structure was confirmed by some reactions. 相似文献
15.
The cyclization of o-aminobenzoylhydrazine ( 1a ) and its 5-methyl derivative 1b with four equivalents and with one equivalent of triethyl orthoacetate (TEOA) was studied. 3-Amino-2-methyl-4(3H)-quinazolinone ( 2a ), 3,4-dihydro-2-methyl-5H-1,3,4-benzotriazepin-5-one ( 3a ) and an imino ether derivative of 2a , N-[2-methyl-4-oxo-3(4H)quinazolinyl]ethanimidic acid ethyl ester ( 4a ) were obtained from the reaction of 1a with four equivalents of TEOA. These results were compared with those of Merour [1] who isolated 2a and 3a using the same conditions. When 1a was treated with one equivalent of TEOA, 2a, 3a , and a new product, 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzenamine ( 5a ) were produced, and 4a was not. Similar results were obtained with the reactions of 1b with TEOA. Authentic samples of oxadiazoles 5a and b were prepared by alternate routes. Novel acid-catalyzed rearrangements of benzotriazepinones 3a and b , to mixtures of aminoquinazolinones 2a and b and oxadiazoles 5a and b , respectively, were found. The different relative amounts of aminoquinazolinones 2 and oxadiazoles 5 which were produced from these rearrangements allowed us to choose between two potential mechanisms for these interesting rearrangements. Treatment of 5-nitrobenzoylhydrazine ( 37 ) with four equivalents of TEOA gave three products which were characterized, but did not lead to benzotriazepinone formation. 相似文献
16.
以N-吡啶基吡唑甲酸和2-氨基-3-甲基苯甲酸为起始原料,经由亲核加成、环化和酰化等多步反应合成了一系列结构新颖的N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类化合物.测试了所合成化合物的杀虫及抑菌活性,结果表明,新化合物大多化合物在200 mg·L^-1浓度下对东方粘虫(Mythimna separataWalker)具有一定的杀虫活性,尤其是N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)乙酰胺(8a)和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3-氯-2,2-二甲基丙酰胺(8e)致死率可达70%;部分化合物在50 mg·L^-1浓度下对油菜菌核病菌的抑菌活性相对较好(54.5%~63.6%),优于triadimefon和chlorantraniliprole;部分化合物如N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3,3-二甲基丁酰胺80和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-4-氟苯甲酰胺(8h)对苹果轮纹病菌具有中等抑菌活性.值得注意的是,化合物8e的杀粘虫活性和对油菜菌核病菌的抑菌活性都较为突出,可用作新农药创制研究的新型参考结构. 相似文献
17.
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
18.
A. Monge J. A. Palop T. Goí A. Martínez E. Fernndez-Alvarez 《Journal of heterocyclic chemistry》1985,22(5):1445-1451
The Vilsmeier-Haack reaction with ethyl 2-(1-methylindole)acetate and N,N-Dimethylamides/phosphorus oxychloride gave (65–85%) of ethyl 2-(3-acyl-1-methylindole)acetates 2 , which when boiled with hydrazine yielded about 90% of 4,5-dihydro-6-methyl-4-oxo-3H[1,2]diazepino[5,6-b]indoles 3. The attempted cyclization of 2-(1-methylindole)acetohydrazones 6 with acyl (acetyl and benzoyl) chlorides/triethylamine, to [1,2]diazepino[5,6-b]indole derivatives was fruitless and the bis(acyl)hydrazones 9 were obtained. Several transformations of 9 are reported. Similarly, the attempted cyclization of 3-indoleacetohydrazones 14 with acetyl chloride/triethylamine to [1,2]diazepino[4,5-b]indole derivatives was also fruitless and the bis(acyl)hydrazones 16 were again obtained. 相似文献
19.
(Z)-3-(α-Alkoxycarbonyl-α-cyanomethylene)-2-oxo-1,2,3,4-tetrahydroquinoxalines 3 and (Z)-3-(α-alkoxycarbonyl-α-cyanomethylene)-3,4-dihydrobenzo[g]quinoxalin-2(1H)-ones 5 possessing various alkoxycarbonyl groups were prepared in good yields directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates 1 with o-phenylenediamine ( 2 ) or with 2,3-diaminonaphthalene ( 4 ), respectively. Furthermore, 2,3-diaminopyridine ( 6 ) and 3,4-diaminopyridine ( 7 ) were reacted with the diethyl ester 1b to give (Z)-2-(α-cyano-α-ethoxycarbonylmethylene)-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one ( 8 ) and (Z)-3-(α-cyano-α-ethoxycarbonylmethylene)-3,4-dihydro-1H-pyrido[3,4-b]pyrazin-2-one ( 9 ), respectively. The structural studies of 3, 5, 8 , and 9 were carried out by nmr experiments in some details. 相似文献
20.
5-Aryl(or benzyl)-3-(2-bromoethyl)-1,3,4-oxadiazol-2(3H)-ones 3 have been prepared. They were reacted with secondary alkylamines without any change of the heterocycle to give amino derivatives 6 , but with primary alkylamines, cyclic transformation occurred to give 1-acylamino-3-alkylimidazolidin-2-ones 7 . In the presence of sodium alcoholate, bromo compounds 3 were transformed into 2-aryl(or benzyl)-4-alkoxycarbonyl-5,6-dihydro-4H-1,3,4-oxadiazines 9 . 相似文献