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1.
The deoxygenated derivative of 3-azidobenzo-as-triazine 1-oxide (II) exists in solution predominantly as 3-azidobenzo-as-triazine form (IVa) but in the crystalline state as tetrazolo[5,]-c]-benzo-as-triazine (IVb), a new fused heteroaromatie ring system. With the pyrido[2,3-e]-as-triazine derivatives, however, both 3-azidopyrido[2,3-e]-as-triazine (X) and pyrido[2,3-e] tetra-zolo[5,1-e]-as-triazine (XI) can be isolated in crystalline form, and these are interconvertible. Another new ring system, the pyrido[2,3-e] triazolo [3,4-c]-as-triazine (XVII) and its derivatives has also been synthesized. 相似文献
2.
Marino Artico Silvio Massa Giorgio Stefancich Romano Silvestri Roberto Di Santo Federico Corelli 《Journal of heterocyclic chemistry》1989,26(2):503-507
The preparation of 5-dimethylaminoethyl-4,6-dioxo-1-phenyl-1,4,5,6-tetrahydropyrazolo[3,4-e]pyrrolo-[3,4-g]indolizine, a derivative of the still unknown tetracyclic parent ring pyrazolo[3,4-e]pyrrolo[3,4-g]indolizine, is reported starting from 1-phenyl-5-(1-pyrryl)pyrazole-4-acetonitrile by PPA catalyzed double cyclization of the related oxalylcyanomethyl derivative and subsequent alkylation. The synthesis of 4,5-bis(isopro-pylaminocarbonyloxymethyl) and 4,5-bis-(cyclohexylaminocarbonyloxymethyl) derivatives of 1-phenyl-1H-pyrazolo[3,4-e]indolizine is also described. The new tricyclic and tetracyclic derivatives were tested as potential antitumor agents. 相似文献
3.
Treatment of 3-aminobenzo-as-triazines with bromoacetaldehyde ethylene acetal give linear tricyclic imidazobenzo-as-triazines, where 3-amino-7-methylbenzo-as-triazine 1-oxide yields the angular isomer. The structures of these compounds have been established by comparing their nmr spectra to those of pyrazolo [5,1-c]- and s-triazolo[5,1-c]benzo-as-triazines obtained form the appropriate azo derivatives by intramolecular cyclization. 相似文献
4.
Giorgio Stefancich Federico Corelli Silvio Massa Romano Silvestri Roberto Di Santo 《Journal of heterocyclic chemistry》1987,24(4):1199-1202
Suitable 1-phenyl-5-(1-pyrryl)pyrazole intermediates underwent Knoevenagel or Wittig intramolecular olefination to give derivatives of 1H-pyrazolo[3,4-e]indolizine, a hitertho unknown tricyclic heteroaromatic system. 相似文献
5.
Giuliana Biagi Irene Giorgi Oreste Livi Clementina Manera Valerio Scartoni 《Journal of heterocyclic chemistry》1999,36(5):1195-1198
Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3, 4 -c]pyrimidmes were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7 , 8 and 9 . Intramolecular cyclization of the ethoxycarbonylhydrazino derivatives 10 gave the tricyclic compounds 11 bearing an hydroxyl group in the 3 position. The v-triazolo-s-triazolopyrimidine derivatives were tested towards the A1 and A2A adenosine receptors in binding assays, but they did not show any receptor affinity. 相似文献
6.
Treatment of 4-chloro-3-nitropyridine (I) with hydrazine hydrate followed by catalytic reduction gave 3-amino-4-hydrazinopyridine (III). Acid-catalyzed cyclizations of III and subsequent dehydrogenation gave pyrido[3,4-e]-as-triazines (V). Treatment of I with guanidine followed by base-catalyzed cyclization gave 3-aminopyrido[4,3-e]-as-triazine 1-oxide (VII). The 1-oxide function was removed by reduction and subsequent dehydrogenation gave the 3-amino derivative (IX). On treatment with hot alkali VII rearranged to a triazolo[4,5-c]pyridine (X). The ultraviolet and nmr spectra of derivatives of the title ring systems are reported. 相似文献
7.
Hashime Kanazawa Sadao Nishigaki Keitaro Senga 《Journal of heterocyclic chemistry》1984,21(4):969-974
Reactions of 6-arylidenehydrazino-1,3-dimethyluracil derivatives with N-bromosuccinimide leading to pyrazolo[3,4-d]pyrimidines, pyrimido[5,4-e]-as-triazines, and pyrimido[4,5-c]pyridazines are described. 相似文献
8.
The condensation of 1-acyl-2-(morpholin-4-yl)cycloalkenes with 3-amino-1-phenyl-1H-pyrazol-5(4H)-ones gave the corresponding 2,3,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinoline and 3,6,7,8,9,10-hexahydrocyclohepta[ d]pyrazolo[3,4-b]pyridine derivatives. Alkylation of 2,3,6,7,8,9-hexahydropyrazolo[3,4-c]-isoquinolines with alkyl halides occurred at the nitrogen atom in the 3-position. The structure of 7-methyl-2,5-diphenyl-2,3,6,7,8,9-hexahydro-1H-pyrazolo[3,4-c]isoquinolin-1-one was proved by X-ray analysis. 相似文献
9.
The synthesis of 1H-pyrazolo[3,4-c]isoquinolin-1-ones was carried out by reacting 3-aryl(heteryl)-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones with 3-amino-1-phenyl-1H-pyrazol-5(4H)-one. The structure of the 7-acetyl-2,4,6,7,8,9-hexahydro-8-hydroxy-5,8-dimethyl-2-phenyl-6-(fur-2-yl)-1H-pyrazolo[3,4-c]isoquinolin-1-one obtained was proved by X-ray diffraction analysis. 相似文献
10.
The compounds prepared in the novel pyridazino[4,3-e]-as-triazine ring system are: 8-chloro-4-methyl-3,4-dihydropyridazino[4,3-e]-as-triazine ( 21 ), 8-chloro-2,4-dimethyl-3,4-dihydropyridazino[4,3-e]-as-triazine ( 23 ), 8-chloro-2-ethyl-4-methyl-3,4-dihydropyridazino[4,3-e]-as- triazine ( 24 ), 4-methyl-3,4-dihydropyridazino[4,3-e]-as-triazine-8-thione ( 25 ), 4-methyl-3,4-dihydropyridazino[4,3-e]-as-triazine ( 26 ), 2,4-dimethyl-3,4-dihydropyridazino[4,3-e]-as-triazine ( 27 ), and 2-ethyl-4-methyl-3,4-dihydropyridazino[4,3-e]-as-triazine ( 28 ). In the novel pyridazino[4,5-e]-as-triazine ring system the following compounds were prepared: 1,2-dihydropyridazino[4,5-e]-as-triazine ( 31 ), 3-methyl-1,2-dihydropyridazino[4,5-e]-as-triazine ( 32 ), 3-ethyl-1,2-dihydropyridazino[4,5-e]-as-triazine ( 33 ), and 1-methyl-1,2-dihydropyridazino[4,5-e]-as-triazine ( 35 ). The preparation of a number of previously unreported intermediates and compounds for structure proof are also described. 相似文献
11.
Zusammenfassung Durch Kupplung von Diazoniumsalzen mit 3-Äthoxycarbonylamino-1-phenyl-5-pyrazolon wurden einige entsprechende Hydrazone (1) hergestellt. Durch thermische Cyclisierung wurden diese Substanzen glatt in 2-Aryl-6-phenyl-3,4,6,7-tetrahydro-2H-pyrazolo[3,4-e]1,2,4-triazin-3,7-dione bzw. in die 2,3,6,7-5H-Tetrahydrotautomeren (2) übergeführt.
Cyclization of hydrazones. III: Syntheses of some pyrazolo [3,4-e]-1,2,4-triazine derivatives
By coupling diazonium salts with 3-ethoxycarbonylamino-1-phenyl-5-pyrazolone a series of arylhydrazones (1) was prepared. These substances were thermally cyclized into 2H-2-aryl-6-phenyl-3,4,6,7-tetrahydropyrazolo[3,4-e]1,2,4-triazine-3,7-diones or into their corresponding 2,3,6,7-tetrahydro-5H-tautomers (2).相似文献
12.
Mokhtar A. Abd ul-Malik Adel M. Kamal El-Dean Shaban M. Radwan Remon M. Zaki 《Journal of heterocyclic chemistry》2021,58(11):2067-2077
A new series of pyrazolopyrazinoselenolotriazolopyrimidines was synthesized by a facile method based on condensation of 5-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]selenolo[3,2-e]pyrazine-6-carbonitrile ( 3 ) with triethyl orthoformate followed by intramolecular cyclization with hydrazine to afford 7-amino-8-imino-3-methyl-1-phenyl-1,8-dihydro-7H-pyrazolo[3″,4″:5′,6′]pyrazino[2′,3′:4,5] selenolo[3,2-d]pyrimidine ( 5 ). The latter compound was utilized as a multipurpose precursor for the construction of other new triazoles fused to the pyrazolopyrazino- selenolopyrimidine moiety. Alternatively, acetylation and chloro-acetylation of compound 3 using acetic anhydride and chloroacetyl chloride yielded the acetyl amino 11 and chloroacetamido 12 derivatives, respectively. Compound 12 underwent nucleophilic substitution upon reaction with morpholine to provide the morpholinyl acetamide 13 . Furthermore, the pyrazolopyridoselenolopyrazine ring system 14 was synthesized by the reaction of the o-amino-carbonitrile 3 with malononitrile. Assignment of the chemical structures for the new compounds was confirmed depending on elemental and spectral techniques. On the other hand, most of the synthesized compounds revealed promising results against various bacterial and fungal strains. 相似文献
13.
By the action of thionyl chloride on 3(5)-R-4-phenacylpyrazole-5(3)-carboxylic acid ( 3c,d ), 3-R-5-phenylpyrano[3,4-c]pyrazole-7-(1H)ones ( 4c,d ) were obtained. When 4c,d were treated with hydrazine hydrate followed by refluxing in ethanol containing acetic acid, 4,7-dihydro-3-R-5-phenylpyrazolo[3,4-d][1,2]-diazepin-8-(1H)ones ( 6c,d ) were formed. Compounds 6c,d , in turn, were refluxed in ethanol saturated with hydrochloric acid to yield 6-amino-1,6-dihydro-3-R-5-phenyl-7H-pyrazolo[3,4-c]pyridin-7-ones ( 7c,d ). Compounds 7c,d could be obtained directly from 5c,d. The starting materials 3c,d were prepared by hydrolysis of the oxime of 3(5)-R-4-phenacyl-5(3)carboalcoxypyrazoles ( 1a,b ). Structural assignments rested on correct elemental analysis, molecular weights determined by mass spectrometry, and spectroscopic evidence. 相似文献
14.
L. M. Mironovich M. A. Ivanov E. P. Koval'chuk 《Chemistry of Heterocyclic Compounds》2001,37(9):1150-1152
8-tert-Butyl-9-oxo-1,2,4-triazolo[4,5-b]-1,2,4-triazolo[3,4-c]-1,2,4-triazine has been synthesized by the interaction of 6-tert-butyl-3-hydrazino-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one with formic acid. The conditions of carrying out the reaction are discussed. Spectral characteristics are given. 相似文献
15.
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
16.
Sadao Nishigaki Misuzu Ichiba Kiyoko Fukami Keitaro Senga 《Journal of heterocyclic chemistry》1982,19(4):769-773
Reaction of 5-arylazo-6-arylidenehydrazino-1,3-dimethyluracils (II), prepared by the treatment of 6-aryl-idenehydrazino-1,3-dimethyluracils (I) with diazotized arylamines, with dimethylformamide dimethylacetal resulted in the formation of pyrimido[5,4-e]-as-triazine (V) system, while the thermolysis of II resulted in the formation of purine (X), v-triazolo[4,5-d]pyrimidine (XII), and pyrazolo[3,4-d]pyrimidine (XIV, XIX) systems in lieu of the expected V. Reasonable mechanisms have been proposed for the formation of the various ring systems in these reactions. 相似文献
17.
Abolghasem Davoodnia Rahele Zhiani Niloofar Tavakoli-Hoseini 《Monatshefte für Chemie / Chemical Monthly》2008,81(2):1405-1407
Starting from 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones, a synthesis pathway to the tricyclic pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines is described. Reaction of 1,5-dihydro-4H-pyrazolo[3,4-d] pyrimidin-4-ones with phosphoryl chloride afforded the corresponding 4-chloro-1H-pyrazolo[3,4-d]pyrimidines. Treatment of these compounds with hydrazine hydrate at reflux temperature gave the hydrazino derivatives, which
were subsequently cyclized to the titled compounds on heating with orthoesters in ethanol. 相似文献
18.
Ring closure of 5, 6-diamino-3-methylthio-as-triazine with 40% aqueous glyoxal provided the 6, 7-dihydrate of the pyrazino[2, 3-e]-as-triazine (4-azapteridine) ring system. The C7 hydroxy group of this dihydrate underwent exchange in methanol or ethanol affording the 7-alkoxy, 6-hydroxy derivatives. 相似文献
19.
P. Molina A. Arques I. Cartagena M. V. Valcarcel 《Journal of heterocyclic chemistry》1986,23(1):43-48
2-Aryl-4-thioxo-1,3-benzothiazines react with thiocarbohydrazide to give the new mesoionic compounds an-hydro 1-amino-5-aryl-2-mercapto-1,3,4-triazolo[3,2-c]quinazolin-4-ium hydroxides. These compounds react with methyl iodide, aldehydes and phenacyl bromides to give 1-amino-5-aryl-2-methylthio-1,3,4-triazolo-[3,2-c]quinazolin-4-ium iodides, 4-arylidenamino-3-(o-aroylamino)phenyl-1H-1,2,4-triazolin-5-thiones and 3-(o-aroylamino)phenyl-6-aryl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines, respectively. These latter compounds by sequential treatment with methyl trifluoromethanesulphonate and triethylamine lead to 3-(o-aroylamino)-phenyl-6-aryl-1-methyl-7-mercapto-1H-pyrazolo[5,1-c]-1,2,4-triazoles. 相似文献
20.
Marjo Merslavi
Andrej Petri
Branko Stanovnik Miha Tiler 《Journal of heterocyclic chemistry》1989,26(3):581-583
The transformations of 7-methyl-7H- and 8-methyl-8H-pyrazolo[4, 3-d]tetrazolo[1, 5-b]pyridazines 1, 2, 9 and 10 into 8-methyl-8H- and 9-methyl-9H-pyrazolo[3, 4-H]-s-triazolo[4, 3-b]pyridazines 7 and 8 , and 1-methyl-1H-and 2-methyl-2H-imidazo[1, 2-b]pyrazolo[3, 4-d]pyridazines 13 and 14 are described. 相似文献