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1.
ABSTRACT The reaction of 1,2,4-triazole with functionalized carbodiimide 2 or 6 under solid K 2CO 3 provide a convenient and regiospecific route to 1-(2-imidazolonyl)-1,2,4-triazole 4 or 1-(2-quinazolonyl)-1,2,4-triazole 8. 相似文献
2.
Summary Thiosemicarbazide reacted with 1,2-diaminobenzene to give 1,2-dihydro-3-thioxo-1,2,4-benzotriazine ( 1) in fairly good yield in a solvent free reaction under microwave irradiation. 1 was condensed with prop-2ynyl bromide in the presence of sodium methoxide to afford the corresponding 3-(prop-2-ynylsulfanyl)-1,2,4-benzotriazine ( 5). Transformation of 5 to 3-methylidene-2,3-dihydro-9 H-thiazolo[2,3- c][1,2,4]benzotriazine ( 6) was performed in the presence of a palladium salt.
Regioselektive Anellierung von 3-(prop-2-inylsulfanyl)-1,2,4-benzotriazin zu Thiazolo[2,3-c][1,2,4]benzotriazin Zusammenfassung Thiosemicarbazid reagierte mit 1,2-Diaminobenzol ohne Lösungsmittel und unter Bestrahlung mit Mikrowellen in guter Ausbeute zu 1,2-Dihydro-3-thioxo-1,2,4-benzotriazin (1), welches in Gegenwart von Natriummethoxid mit Prop-2-inylbromid zum entsprechenden 3-(Prop-2-inylsulfanyl)-1,2,4-benzotriazin (5) kondensiert wurde. Die Umsetzung von5 zu Methyliden-2,3-dihydro-9H-thiazolo[2,3-c] [1,2,4]benzotriazin (6) gelang unter Palladiumkatalyse. 相似文献
3.
5-Benzylidene-3-(p-chlorophenyl)-2-aminothiocarbonyl-1,2,4-triazine (2) was prepared via condensation of oxazolinone (1) with thiosemicarbazide. Fused 1,2,4-triazine derivatives (3, 4 and 9) were synthesized from the reaction of compound 2 with ω-bromomethyl aryl ketones, ethyl chloroacetate, and acetic anhydride. Treatment of 4 with acetic anhydride and aromatic aldehydes yielded the corresponding acetyl, diacetyl derivatives (6 and 7) and 7-benzylidene-5-(p-chlorophenyl)-4-thioxo-3-arylidene-1,2,4-triazino [2,1-a]-1,2,4-triazine-1,8-diones (8). The electron impact mass spectra of both the above series of compounds have also been recorded and their fragmentation pattern is discussed. All synthesized fused 1,2,4-triazine derivatives were primary in vitro screened for their antimicrobial and antitumor activity. 相似文献
4.
Convenient Synthesis of Some 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines Bearing 3-Methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}moiety as Possible Antimicrobial Activity
4-Amino-4H-3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazole-5thi-ol ( 1) was condensed with various substituted aromatic aldehydes or acid chlorides to yield a series of arylideneamines 2 or aroylamines 3. These were easily cyclized to the corresponding 6-aryl-3-methylthio7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl-1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles ( 4) on treatment with palladium-on-charcoal or phosphorus oxychloride. Compounds 4 were also prepared directly via the reaction of 1 with aromatic carboxylic acids in the presence of phosphorus oxychloride. Cyclocondensation of 1 with a variety of two-carbon cyclizing reagents, namely chloroacetone, pyruvic acid, benzoylformic acid, and benzoin led to the formation of 3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines ( 5?8). Some of the newly synthesized compounds were tested for their antibacterial and antifungal activity against a variety of microorganisms. 相似文献
5.
ABSTRACT 1,2,4-Triazines have been prepared from the one-pot condensation reaction of acid hydrazide ( 1), ammonium acetate and dicarbonyl compounds ( 2) on the surface of silica gel in the presence of triethylamine under microwave irradiation. 相似文献
6.
The novel ring system, 6 H-1,2,4-triazino[4,3— b]1,2,4-triazolo[3,4— f]-pyridazine was prepared either by ring closure of 1-(1-ethoxycarbonylethylene)-2-(1,2,4-triazolo[4,3— b]pyridazinyl-6)-hydrazine derivatives ( 4, 5, 7) in polyphosphoric acid or of a hydrazine 15 derived from pyridazino-1,2,4-triazine under the action of triethyl orthoformate. Compound 8 showed a positive inotropic effect.
Über Pyridazinring enthaltende Verbindungen, 20. 6H-1,2,4-Triazino[4,3—b]1,2,4-triazolo[3,4—f]pyridazin, ein neues angulares Ringsystem Zusammenfassung Das neue Ringsystem 6H-1,2,4-Triazino[4,3—b]1,2,4-triazolo[3,4—f]-pyridazin wurde entweder durch Ringschluß der1-(1-Ethoxycarbonylethylen)-2-(1,2,4-triazolo[4,3—b]pyridazinyl-6)-hydrazin-Derivate(4, 5, 7) 4, 5, 7 in Polyphosphorsäure, oder aus einem von Pyridazino-1,2,4-triazin abgeleiteten Hydrazin15 durch Ringschluß mit Orthoameisensäuretriethylester hergestellt. Verbindung8 zeigte einen positiven inotropen Effekt. 相似文献
7.
Thermal cyclization of 3-R-5-chloro-1,2,4-triazoles (R = Cl, Ph) afforded 2,6,10-tri-R- tris[1,2,4]triazolo[1,5- a:1′,5′ c:1″,5″- e][1,3,5]triazines 5 (R = Ph) and 7 (R = Cl). These compounds are first representatives of this class of heterocycles, whose structures were unambiguously established. Treatment of these compounds with nucleophiles (H 2O/NaOH, NH 3) results in the triazine ring opening to give compounds consisting of three 1,2,4-triazole rings linked in a chain. For example, treatment of cyclic compound 5 with aqueous alkali affords 3-phenyl-1-3-phenyl-1-(3-phenyl-1 H-1,2,4-triazol-5-yl)-1,2,4-triazol-5-yl-1 H-1,2,4-triazol-5-one. Treatment of 3,7,11-triphenyltris[1,2,4]triazolo[4,3- a:4′,3′ c:4″,3″- e][1,3,5]triazine ( 2) with HCl/SbCl 5 leads to the triazine ring opening giving rise to 5-(3-chloro-5-phenyl-1,2,4-triazol-4-yl)-3-phenyl-4-(5-phenyl-1 H-1,2,4-triazol-3-yl)-1,2,4-triazole. Thermal cyclization of the latter produces 3,7,10-triphenyltris[1,2,4]triazolo[1,5- a:4′,3′ c:4″,3″- e][1,3,5]triazine ( 13). Thermolysis of both cyclic compound 2 and cyclic compound 13 is accompanied by the Dimroth rearrangement to yield 3,6,10-triphenyl-tris[1,2,4]triazolo[1,5- a:1′, 5′- c:4″,3″- e][1,3,5]triazine ( 14). Compounds 13 and 14 are the first representatives of cyclic compounds with this skeleton. 13C NMR spectroscopy allows the determination of the isomer type in a series of tris[1,2,4]triazolo[1,3,5]triazines.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 706–712, March, 2005. 相似文献
8.
Abstract Recently, we have prepared a number of N-ethoxycarbonyl-N′-(2-azinyl)thioureas, which could be cyclized by oxidation into derivatives of 1,2,4-thiadiazolo/2,3-a/azines. 相似文献
9.
Cyclic α-oxo-α-(1,2,4-triazolyl)ketene S,S-acetals 1a-e react with hydrazine affording the substituted pyrazolyl-1,2,4-triazoles 3a-e. With hydroxylamine hydrochloride under basic conditions the substituted isoxazolyl-1,2,4-triazoles 5a-c are obtained. 相似文献
10.
An unequivocal synthesis of 5-chloro-7-methyl- ( 8) and 7-methyl-1,2,4-triazolo[1,5- a]pyrimidine ( 10) from 2-amino-4-chloro-6-methylpyrimidine ( 5) through the corresponding amidine 6 and formamide oxime 7 was developed. It was unambigously shown by comparison of the chemical shifts and the magnitude of coupling constants that the compounds obtained by condensation of 3-amino-1,2,4-triazole ( 12) and ethyl acetoacetate ( 13) and some further transformations are isomeric 5-methyl substituted 1,2,4-triazolo[1,5- a]pyrimidines 1, 9, and 11.
Eine eindeutige Synthese einiger substituierter 1,2,4-Triazolo[1,5-a]pyrimidine Zusammenfassung Es wurde ein eindeutiger Syntheseweg für 5-Chlor-7-methyl- (8) und 7-Methyl-1,2,4-triazolo[1,5-a]pyrimidin (10) ausgehend von 2-Amino-4-chlor-6-methylpyrimidin (5) über das entsprechende Amidin6 und das Formamidoxim7 entwickelt. Durch Vergleich von chemischen Verschiebungen und Kopplungskonstanten konnte eindeutig gezeigt werden, daß die Verbindungen, die bei der Kondensation von 3-Amino-1,2,4-triazol (12) and Ethylacetoacetat (13), sowie einige weitere Transformationsprodukte, isomere 5-Methylsubstituierte 1,2,4-Triazolo[1,5-a]pyrimidine sind (1,9,11). 相似文献
11.
The synthesis of some 3-substituted amino-6,7-diphenyl-1,2,4-triazolo[4,3-b][1,2,4]triazines ( 15) by cyclodesulfurisation of the corresponding N-(5,6-diphenyl-1,2,4-triazin-3-yl)-N-[substituted thio (carbamoyl)]hydrazines ( 3) using dicyclohexylcarbodiimid ( DCC) and mercuric chloride is described. Moreover, trials to prepare 3-substituted amino-7-hydroxy-6-methyl-1,2,4-triazolo[4,3-b][1,2,4]triazines were not successful.
Synthese einiger substituierter Triazolo[4,3-b][1,2,4]-triazine als potentielle Antikrebswirkstoffe Zusammenfassung Es wird die Synthese einiger 3-substituierter Amino-6,7-diphenyl-1,2,4-triazolo[4,3-b][1,2,4]-triazine (15) mittels Cyclodesulfurisierung der entsprechenden N-(5,6-Diphenyl-1,2,4-triazin-3-yl)-N-[subst.thio(carbamoyl)]-hydrazine (3) unter Verwendung von Dicyclohexylcarbodiimid (DDQ) beschrieben. Versuche zur Herstellung von 3-substituierten Amino-7-hydroxy-6-methyl-triazolo[4,3-b][1,2,4]-triazinen schlugen fehl. 相似文献
12.
A straightforward method has been developed for the synthesis of 1-phenyl-imidazo [2,1-c][1,2,4]triazole derivatives 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones derivatives 6a–g starting from 5-amino-1-phenyl[1,2,4]triazole and p-toluenesulfonic acid (PTSA). This methodology affords a number of 1-phenyl-imidazo [2,1-c][1,2,4]triazoles 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones 6a–g in reasonable yields and short reaction times. The structures of all new compounds were elucidated using infrared, 1H and 13C NMR, and high-resolution mass spectrometry. Some of the newly synthesized compounds were screened for their antimicrobial activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications ® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
13.
The reaction of trimethylsilyl- and pentafluorophenyl- N-sulfinylamine respectively with 3,5-dihalogeno-1,2,4-trithia-3,5-diborolanes yields the 1,2-dithia-4-aza-3,5-diborolidines 1-3. Tert-butyl- N-sulfinylamine and 3,5-dimethyl-1,2,4-trithia-3,5-diborolane react analogous. Other N-sulfinylamines however split the disulfane bridge in 3,5-dimethyl-1,2,4-trithia-3,5-diborolane and the 1,4-dithia-2-aza-3,5-diborolidines 5A- 7(A) are formed. Besides of boroxines, cyclo-2,4,6-trimethyl-1,3-dioxa-5-aza-2,4,6-triboranes and cyclo-2,4,6-trimethyl-1-oxa-3,5-diaza-2,4,6-triboranes are formed as byproducts, 8–10 have been isolated. In 1,2,4-trithia-3,5-diborolanes and 1,2-dithia-4-aza-3,5-diborolidines the bromo-atoms can be substituted by alkyl ( 13, 14), by amino ( 15–20) and by isothiocyanato groups. The compounds were characterised analytically and spectroscopically (MS; NMR: 1H, 11B, 19F, 29Si; IR). 相似文献
14.
A method of one-step C-C coupling of 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane ( 1a) and 1,8-bis(2,6-dimethylphenoxy)-3,6-dioxaoctane ( 1b) with 3-methylthio- ( 2) and 3-amino-1,2,4-triazine ( 3) and 3-aryl-1,2,4-triazin-5-one ( 6-8) has been described. The reaction of compounds 1a,b with compounds 2 and 3 in the presence of trifluoroacetic acid results in the addition of the dimethylphenoxy group to the unsubstituted C(5) carbon atom of the triazine ring. The reactions of triazinones 6-8 with compounds 1a,b in a mixture of trifluoroacetic acid and organic anhydrides are accompanied by the acylation of the nitrogen atom adjacent to the reaction center and affords bis[(3-R-1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)-2,6-dimethylphenoxy]-3-oxapentane or -3,6-dioxaoctane. The obtained adducts can smoothly be oxidized under mild conditions to form more stable products of nucleophilic hydrogen substitution in the triazine ring. The extraction and transport of Ca 2+ and Mg 2+ cations through an organic membrane by the compounds synthesized are discussed.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2210–2215, October, 2004. 相似文献
15.
A three-component condensation of 3,4,5-triamino-1,2,4-triazole ( 1) with aromatic aldehydes 2a–f and dimedone ( 3) or cyclohexanone ( 8) afforded partially hydrogenated 9-aryl-[1,2,4]triazolo[5,1- b]quinazolin-8-ones. The structure of 2-amino-6,6-dimethyl-3-(4-nitrobenzylidene)amino-9-(4-nitrophenyl)-5,6,7,9-tetrahydro[1,2,4]triazolo[5,1- b]quinazolin-8-one ( 4e) was confirmed by X-ray diffraction data.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1178–1182, July, 2006. 相似文献
16.
Abstract 1,2,4-triazole and 1,3,4-thiadiazole derivatives are still considered a viable lead structure for the synthesis of more efficient antimicrobial agents having a broad spectrum of activity. This study presents the synthesis and antimicrobial evaluation of a new series of substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Reaction of 4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thione with ethyl bromoacetate yields the corresponding ethyl acetate ( 1). In the subsequent reaction with 100% hydrazine hydrate, the hydrazide ( 2) was obtained, which was converted with isothiocyanates to new acyl derivatives of thiosemicarbazide ( 3a– l). The cyclization of these compounds in alkaline media resulted in the formation of new derivatives of 1,2,4-triazole ( 4a–i), whereas in acidic media new derivatives of 1,3,4-thiadiazole ( 5a, b, g) were obtained. All synthesized compounds were screened for their in vitro antimicrobial activities. 相似文献
17.
A facile synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives under focused microwave irradiation (FMWI) is reported. Arylamidoximes 1a– i and dicyclohexylcarbodiimide (DCC) were carried out in DMF under FMWI to obtain 1,2,4-oxadiazoles 2a– i in 61–81% yields. All compounds exhibited antiproliferative activities in vitro against three human cancer cell lines HCT-116, PC-3, and SNB-19. 相似文献
18.
Abstract 5-Amino-3-methyl- and 5-amino-3-phenylisothiazoles ( 3a and 3b) afforded 1 : 1 adducts with aromatic nitriles and imidates. On the basis of their spectral data and the structure of hydrolysis products, the adducts were identified as 3-substituted 5-(2-aminovinyl)-1,2,4-thiadiazole derivatives ( 2a-g), where ring transformation took place from isothiazole to 1,2,4-thiadiazole. 相似文献
19.
A preparative method for the synthesis of 2-alkyl-1,2,4-benzotriazin-3(2 H)-ones 3 was developed. The method involves treatment with sodium cyanate of 2-alkylbenzotetrazinium tetrafluoroborates, which exist
in solutions in equilibrium with o-(alkylazo)aryldiazonium tetrafluoroborates. Reduction of compounds 3 with zinc in acetic acid afforded 2-alkyl-1,4-dihydro-1,2,4-benzotriazin-3(2 H)-ones.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 346–349, February, 2006. 相似文献
20.
A general method for inclusion of the 15N label into the position 1 of 6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazin-7-one by using K 15NO 3 has been developed. 相似文献
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