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1.
Yoshinori Tominaga Kenji Sasaki Raymond N. Castle 《Journal of heterocyclic chemistry》1998,35(5):1219-1234
Reactions of 1,3-disubstituted 5-aminopyrazole-4-carbonitrile derivatives 3a-o with dimethyl acetylenedicarboxylate in the presence of potassium carbonate in dimethyl sulfoxide gave the corresponding dimethyl 1,3-disubstituted pyrazolo[3,4-b]pyridine-5,6-dicarboxylates 4a-o which were allowed to react with excess hydrazine hydrate under ethanol refluxing conditions followed by heating at 250-300° to give 1,3-disubstituted 4-amino-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones 7a-s in good yields. Similarly, 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4′3′:5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones 10a-c were obtained from alkyl 1,3-disubstituted 5-aminopyrazole-4-carboxylates 8a-c . These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e]pyrazolo[3,4-b]pyridine-5,7-diones 13a-c prepared by reactions of 5-aminopyrazoles (8e-g) with methyl 1-methyl-4-methylthio-2,5-dioxo-1H-pyrrole-3-carboxylate (11a) followed by the Gould/Jacobs reaction. 1-Methyl-4-methylthio-2,5-dioxo-1H-pyrrole-3-carbonitrile smoothly reacted with 2-aminobenzimidazoles to give the corresponding 5-amino-3-methyl-1H-pyrrolo[3′4′:4,5]pyrimido[1,2-a]benzimidazole-1,3(2H)-diones 16a-e , which were readily converted to the desired 12-aminopyridazino[4′,5′:4,5]pyrimido-[1,2-a]benzimidazole-1,4(2H,3H)-diones 17a-e in good yields. Other pyridazinopyrimidine derivatives were also obtained by the reaction of the corresponding 2-aminoheterocycles with the maleimide in good yields. Substituted anilines reacted 11b in refluxing methanol to give the corresponding methyl 4-phenylamino-1-methyl-2,5-dioxo-1H-pyrrole-3-carboxylates 25a-e which were converted in good yields to 2-methylpyrrolo[3,4-b]quinoline derivatives 26a-e by heating in diphenyl ether. Reaction of 26a-c with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones 27a-e in good yields. The desired 10-aminopyridazino[4,5-b]pyridazine-1,4(2H,3H)-diones 30a-e were obtained in good yields by the chlorination of 4a-e with phosphorus oxychloride followed by aminolysis with 28% ammonium hydroxide. Some pyridazino[4,5-a][2.2.3]cyclazine-1,4(2H,3H)-diones 37a,b as luminescent compounds were synthesized via several steps from indolizine derivatives. The key intermediates, dimethyl 6-dimethylamino[2.2.3]cyclazine-1,2-dicarboxylates 34, 36 , were synthesized by the [8 + 2] cycloaddition reaction of the corresponding 7-dimethylaminoindolizines 33, 35 with dimethyl acetylenedicarboxylate in the presence of Pd-C in refluxing toluene. Some were found to be more efficient than luminol in light production. 4-Amino-3-methylsufonyl-1-phenyl-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (7r) , 10-hydroxypyridazino[4,5-b]-quinoline-1,4(2H,3H)-diones 27a-e , and 10-aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones 30a-e showed the greatest chemiluminescence intensity in the presence of hydrogen peroxide peroxidase in a solution of phosphate buffer at pH 8.0. 相似文献
2.
David T. Connor Patricia A. Young Maximilian Von Strandtmann 《Journal of heterocyclic chemistry》1981,18(4):697-702
3-Aminochromone and 3-aminocoumarin were condensed with diethyl ethoxymethylenemalonate and with dimethyl acetylenedicarboxylate to give intermediates, which were thermally cyclized to give 4,10-dihydro-4,10-dioxo-lH-[1]-benzopyrano[3,2-b]pyridinecarboxylates and 1,5-dihydro-1,5-dioxo-4H-[1]-benzopyrano-[3,4-b]pyridinecarboxylates. 2-Aminochromone was converted to 4,5-dihydro-4,5-dioxo-1H-[1]-benzopyrano-[2,3-b]pyridinecarboxylate via an intermediate condensation product with diethyl ethoxymethylenemalonate. These esters were hydrolyzed to the corresponding carboxylic acids (21, 30, 36, 50, and 60). Attempts to prepare 4,5-dihydro-4,5-dioxo-1H-[1]-benzopyrano[4,3-b]pyridinecarboxylates from 4-aminocoumarin were unsuccessful. 相似文献
3.
Lhassane Ismaïli Bernard Refouvelet Jean Franois Robert 《Journal of heterocyclic chemistry》1999,36(3):719-722
The new pyrazolo[4,3-c]quinolin-3-one derivatives 3a-c and 6a-c were prepared by the following three steps: first the preparation of ethyl 4-hydroxyquinoline-3-carboxylate derivatives 1 and 4 by reaction of isatoic anhydrides and ethyl malonate and ethyl acetoacetate respectively, then chloration of 1 and 4 with phosphorus oxychloride to give 2 and 5 and finally the condensation of 2 and 5 with hydrazine and its derivatives. In addition, the successful synthesis of oxazolo[4,5-c]quinoline-2,4-diones 9a-f are reported. 相似文献
4.
The reaction of 5a-acetyl-6-ethoxycarbonyl-5a,6a-dihydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine-3-carbonitrile ( 1a ) with benzylamine gave ethyl l-benzyl-5-cyano-8a,9-dihydro-2-methyl-1H-pyrrolo[3,4-e]-pyrazolo[1,5-a]pyrimidine-8a-carboxylate ( 2a ), in addition to 5-acetyl-3-benzylamino-1-(4-cyanopyrazol-3-yl)- 2-pyridone ( 3 ). Reaction of 1a with aniline gave ethyl 6-acetyl-8-anilino-3-cyano-7,8-dihydro-4H-pyrazolo-[1,5-a][1,3]diazepine-8-carboxylate ( 4 ), in addition to ethyl 3-cyano-7-methyl-6-pyrazolo[1,5-a]pyrimidine-acrylate ( 5 ). On the other hand, the same reactions of 1b with benzylamine or aniline gave 2b or 8b , respectively. Though catalytic hydrogenation of 1a over 5% palladium-carbon proceeded by ring fission of cyclopropane ring to give 9 , 1a (or 1b ) afforded 4,5-dihydro derivatives ( 13 or 15 ) by catalytic hydrogenation over platinum oxide. The reactivity of 5-methoxy-4,5,5a,6a-tetrahydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine ( 16 ), which are related analogs of 1a,b , is also described. 相似文献
5.
Yoshihisa Okamoto Isao Togo Yoshihisa Kurasawa Kaname Takagi 《Journal of heterocyclic chemistry》1986,23(6):1829-1831
The reactions of multifunctional compounds 2a, b, c, 3a, b and 4a, b which were readily obtained from 4-amino-1H-1,5-benzodiazepine-3-carbonitrile 1 with orthoesters are described, and derivatives of pyrazolo-[3,4-d]pyrimidines 5 , pyrimido[1,6-a]benzimidazole 9 , and pyrazolo[3′,4′:4,5]pyrimido[1,6-a]benzimidazole 10 are synthesized. 相似文献
6.
1-Unsubstituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with 1-substituted and 1,1-disubstituted ureas in boiling acetic acid to give 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones. In contrast, the reaction of these amines with nitrourea in dioxane affords novel 3-alkyl/aryl-3-ureido-1H,3H-quinoline-2,4-diones or 9b-hydroxy-3a-alkyl/aryl-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones, which can smoothly be dehydrated to 3a-alkyl/aryl-3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones. All three types of products can be converted to 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones by refluxing in acetic acid. 相似文献
7.
Kaname Takagi Tomoji Aotsuka And Hikari Morita Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1986,23(5):1443-1449
Reactions of 4-ethoxycarbonylamino-1H-1,5-benzodiazepine-3-carbonitrile (2) with aliphatic primary amines gave 1-substituted 4-(2-aminoanilino)pyrimidin-2(1H)-one-5-carbonitriles 3. Analogous reactions of 2 with aromatic primary amines afforded 2-(2′-anilino-1′-cyanovinyl)benzimidazoles 5 and 6. Upon treatment with triethylamine, 3 underwent intramolecular cyclization to give 3-substituted 5-aminopyrimidino[4,5-b]-[1,5]benzodiazepin-2(3H,11H)-ones 8 . Heating of 3 with p-toluenesulfonic acid in ethanol gave 2-substituted pyrimidino[1,6-a]benzimidazol-1(2H)one-4-carbonitriles 9 . Reactions of 2 with hydrazines were also described. Mechanistic pathways are proposed to account for the products. 相似文献
8.
Oxidative amination of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with primary alkylamines and potassium amide in liquid ammonia gives rise to the corresponding 4-amino derivatives as the major products. The reactions with acyclic secondary amines are accompanied by annelation of the pyrrole moiety to the starting heterosystem to form 1-R-3-R"-6,8-dimethylpyrrolo[2",3";3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones. The reaction with piperidine as the aminating agent occurs exclusively as aminodehalogenation. The Sonogashira cross-coupling of 4-amino-3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones with terminal alkynes affords 1-R-2-R"-6,8-dimethylpyrrolo[3",2";3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones. 相似文献
9.
Some 5H-pyrimido[4,5-e](1,2,4)-triazolo[3,4-b](1,3,4)-thiadiazine-7,9-(6H,8H)-diones (4 a–d) have been synthesised by the condensation of 3-alkyl-4-amino-5-mercapto-(1,2,4)-triazoles (1 a–d) with 5-bromobarbituric acid (2a). Similarly some 9a-nitro-5H-pyrimido[4,5-e](1,2,4)-triazolo[3,4-b](1,3,4)-thiadiazine-7,9(8H,9aH)-diones (5 a–d) have been obtained by the condensation of1 a–d with 5-bromo-5-nitrobarbituric acid (2b) and final cyclisation withPPA. The structures have been confirmed by PMR spectra and analytical results.
Pyrimido[4,5-e](1,2,4)-triazolo[3,4-b](1,3,4)-thiadiazin-7,9(6H,8H)-dione
Zusammenfassung Es wurden einige 5H-pyrimido[4,5-e](1,2,4)-triazolo[3,4-b](1,3,4)-thiadiazin-7,9(6H,8H)-dione (4 a–d) mittels Kondensation von 3-Alkyl-4-amino-5-mercapto-(1,2,4)-triazolen (1 a–d) mit 5-Brombarbitursäure (2 a) dargestellt. Des weiteren wurden einige 9a-Nitro-5H-pyrimido[4,5-e](1,2,4)-triazolo[3,4-b](1,3,4)-thiadiazin-7,9(8H,9aH)-dione (5 a–d) über die Kondensation von1 a–d mit 5-Brom-5-nitrobarbitursäure (2 b) und anschließender Cyclisierung mitPPA synthetisiert. Die angeführten Strukturen wurden mittels PMR-Spektren und analytischen Daten abgesichert.相似文献
10.
Sonogashira cross-coupling of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with terminal alkynes afforded the corresponding 3-(alkyn-1-yl) derivatives. Oxidative amination of the latter compounds with primary alkylamines was accompanied by heterocyclization to give 6,8-dimethylpyrrolo[3",2":3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones. 相似文献
11.
Konstantinos E. Litinas Demetrios N. Nicolaides Evangelia A. Varella 《Journal of heterocyclic chemistry》1990,27(3):769-774
Regioselective 1,3-dipolar cycloaddition of nitrile oxides 5a-c to ethyl o-hydroxycinnamate (3) gave the corresponding ethyl trans-3-aryl-4,5-dihydro-5-(2-hydroxyphenyl)-4-isoxazolecarboxylates 6a-c . Their structure was confirmed by reductive cleavage to 1 and compounds 9a-c . Compounds 6a-c afforded upon heating in the presence of pyridine the 3-aryl-4H-[1]benzopyrano[3,4-d]isoxazol-4-ones 11a-c . Compound 10c was also isolated from 6c and transformed thermally into 11c . 相似文献
12.
E. S. Denislamova N. V. Bubnov Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2011,47(9):1362-1365
Methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 3-methyl-4-phenyl-1H-pyrazol-5-amine to give methyl 7-arylcarbamoyl-6-aroyl-2-methyl-3-phenylpyrazolo[1,5-a]-pyrimidine-5-carboxylates. The molecular and crystalline structures of methyl 6-benzoyl-7-(4-chlorophenylcarbamoyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylate were studied by X-ray analysis. 相似文献
13.
Onofrio Migliara Salvatore Petruso Vincenzo Sprio 《Journal of heterocyclic chemistry》1980,17(3):529-531
Reaction of 4-acyl-3H-imidazo[1,5-b]pyridazine-5,7-(6H)diones with hydrazine hydrate gave 3R-5R′-8-oxo-1,4,7,8-tetrahydropyridazino[4,5-c]pyridazine together with 3R-5R′-8-oxo-7,8-dihydropyridazino[4,5-c]pyridazine derivatives. Their structures were assigned by means of elemental analyses and spectroscopic data (ir, uv, nmr and ms). The conclusive structural elucidation involved the fact that 2R-4-ethoxycarbonyl-3H-imidazo[1,5-b]pyridazine-5,7-(6H)-diones treated with hydrazine hydrate afforded 3R-5,8-dioxo-1,4,5,6,7,8-hexahydropyridazino-[4,5-c]pyridazine which, upon dehydrogenation, gave products previously reported in the literature. 相似文献
14.
To determine the structures of two isomeric products, 2-phenacylidene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one (2) and 3-phenacylidene-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (3) obtained by condensation of 2,3-diaminopyridine (1) with ethyl benzoylpyruvate [1–3], these compounds were hydrolyzed to give 2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (4) and 3-methyl-1H-pyrido[2,3-b]pyrazin-2-one (5) , respectively [4,5]. Both hydrolysates 4 and 5 were hydrogenated to afford 2-methyl-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one (6) and 3-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (7) . The latter compound was identical with an unequivocally synthesized compound providing proof for the structures of all these compounds. 相似文献
15.
The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-c]pyrrole-2,5-diones (5) and 4-hydroxy-1,2,6,7-tetrahydro-5H-pyrrolo[3,4-b]pyridine-2,5-diones (6) by reacting 1,5-diaryl-pyrrolidine-2,4-diones (1) and 1,5-diaryl-1,5-dihydro-4-amino-2H-pyrrol-2-ones (3) with bis-2,4,6-trichlorophenyl malonates (4) is described.Dedicated to Prof. Dr. Dr. h. c.O. Kratky, Graz, on the occasion of his 80th birthday. 相似文献
16.
Yasumitsu Tamura Ling Ching Chen Masanobu Fujita Yasuyuki Kita 《Journal of heterocyclic chemistry》1980,17(1):1-4
The Synthesis of novel 1-substituted 3-anilino-4-diethylaminomethyl-5-oxo-3,4-dehydro-piperidines and 2-substituted 1,2,3,5,6,11-hexahydro-5-phenyl-4H-pyrido[3,4-b][1,5]benzo diazepin-4-ones from the β-arylaminovinylketones derived from N-substituted piperidine-3,5-diones is described. 相似文献
17.
Cyclization of thioglycolic acids derivatives 3a-d gave isoindolo[1,2-b]thieno[2,3(3,2 or 3,4)-e][1,3]-thiazocines 4a-d . Isoindolo[2,1-a]thieno[2,3(3,2 or 3,4)-f][1,4] or [1,5]diazocines 10b or 11a-c were synthesized from Beckmann or Schmidt rearrangement of the ketones 7a-c . 相似文献
18.
Shuntaro Mataka Kazufumi Takahashi Masashi Tashiro 《Journal of heterocyclic chemistry》1981,18(6):1073-1075
The reaction of 3,4-dibenzoyl-1-methyl-2,5-diphenylpyrrole ( 1 ) and -1-phenylpyrazole ( 2 ) with methylamines ( 3a-c ) afforded pyrrolo[3,4-c]pyridine ( 4 ), and isomeric 2H-pyrazolo[3,4-c]pyridines ( 5a-c ) and [4,3-c]pyridines ( 6a-c ), respectively. 相似文献
19.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
20.
This paper describes the synthesis of a new series of 4-amino-1-(unsubstituted and chloro or fluoro substituted benzyl)-7,8-dihydro-6H-pyrazolo[3,4-b]quinolin-5-ones 8 and the corresponding 7,8-dihydro-6H,9H-pyrazolo[3,4-b]quinoline-4,5-diones 13 . The derivatives obtained by reaction of these compounds with sodium azide in concentrated sulfuric acid are also reported. 相似文献