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1.
R. I. Vas’kevich P. V. Savitskii E. B. Rusanov V. I. Staninets 《Russian Journal of Organic Chemistry》2010,46(11):1682-1686
1-(6-Methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)-4-arylthiosemicarbazides treated with methyl iodide in the presence of sodium
acetate in ethanol convert into 6-methyl-3-arylamino[1,2,4]-triazolo[4,3-b][1,2,4]triazin-7(1H)-ones. In reaction with dicyclohexylcarbodiimide 6-methyl-3-arylamino[1,2,4]triazolo[3,4-c][1,2,4]triazin-5(1H)-ones were obtained which at heating in alcohol solution in the presence of sodium acetate or at 262–272°C underwent the
Dimroth rearrangement to give 3-methyl-7-arylamino[1,2,4]triazolo[5,1-c][1,2,4]-triazin-4(8H)-ones. 相似文献
2.
M. A. El-Badawi A. A. El-Barbary Y. M. Lokshaa Mai El-Daly 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):587-596
Some of novel N , N '-bis-(1,2,4-triazin-4-yl)dicarboxylic acid amides ( 2-5 ) and thiadiazolo[2,3- b ][1,2,4]triazin-7-yl carboxylic acid derivatives ( 6 , 7 ) were prepared by heating 4-amino-6-methyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine ( 1 ) with different dicarboxylic acids (oxalic, malonic, fumaric, maleic, succinic, and phthalic acids respectively) in POCl 3 . Refluxing 1 with 1-chloro-2,4-dinitrobenzene in DMF yielded 3-methyl-6-nitro-10 H -benzo[1,2,4]thiadiazino[2,3- c ][1,2,4]triazin-4-one ( 8 ). Condensation of 1 with 2,4-pentandione in refluxing acetic acid furnished 6-methyl-4-(1-methyl-3-oxobut-1-enylamino)-3-thioxo-3,4-dihydro-2 H -[1,2,4]triazin-5-one ( 9 ). 3,8-D imethyl[1,2,4] triazino[3,4- b ][1,3,4]thiadiazine-4,7-dione ( 11 ) was prepared by refluxing 1 with 2-bromopropionyl bromide in anhydrous benzene to afford the corresponding N -acetylated derivative 10 , which was cyclized by using triethylamine. Also, some triazinylquinazolinones 13a , b were obtained by fusion of 1 with 6-bromo(and/or 6,8-dibromo)-2-methyl-3,1-benzoxazin-4 H -ones. 相似文献
3.
L. M. Mironovich M. V. Kostina A. Yu. Podol’nikova 《Russian Journal of Organic Chemistry》2013,49(5):758-760
By reaction of carbonyl compounds with 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c]-[1,2,4]triazine-8-carbonitrile 3-tert-butyl-8-R-4,6,9,10-tetrahydropyrimido[4′,5′:3,4]pyrazolo[5,1-c][1,2,4]-triazine-4,10-diones and (3-tert-butyl-4-oxo-8-cyano-4,6-dihydropyrazolo[5,1-c][1,2,4]triazin-7-yl)acetamide were obtained. 相似文献
4.
A new, efficient, catalyst-free, one-pot, three-component method for the synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines using 3,5-diamino-1,2,4-triazoles, cyanamide, and triethyl orthoformate is developed. The reaction proceeds smoothly under microwave-assisted heating. Advantages of the method include using easily available reagents, short reaction times, and operational simplicity. 相似文献
5.
Anton V. Dolzhenko Giorgia Pastorin Anna V. Dolzhenko Wai Keung Chui 《Tetrahedron letters》2008,49(50):7180-7183
A new practical synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines is developed. The triazine ring closure of 5-guanidino-3-phenyl-1,2,4-triazole with trichloroacetonitrile proceeds chemo- and regioselectively depending on the nature of the solvent. Conducting the reaction in toluene provided 7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine as the product, which can be further aminated efficiently with replacement of the trichloromethyl group. 相似文献
6.
Yuzuru Sanemitsu Yoshinori Nakayama Masao Shiroshita 《Journal of heterocyclic chemistry》1983,20(6):1671-1675
A regioselective synthesis of 2-aminotriazinones 6a-d is reported, by reaction of 3-methylthio-1,2,4-triazinones 5a-d with O-(2,4-dinitrophenyl)hydroxylamine (2) as an amino-transfer agent. A spectroscopic study and an unequivocal synthesis of 2-amino-4-methyl-6-phenyl-1,2,4-triazinedione ( 11a ) has shown the site of amination to be N2 of the 1,2,4-triazinone ring. Subsequent reaction of 2-amino-1,2,4-triazinones 6a-b with amines, followed by ring closure with aliphatic acids provided [1,2,4]triazolo[2,3-b][1,2,4]triazine-7(1H)ones 13a-e. Conversion of [1,2,4]triazolo[2,3-b][1,2,4]triazinone 13c to unsubstituted [1,2,4]triazolo[2,3-6][1,2,4]triazine (15) was attained. 相似文献
7.
Britsun V. N. Esipenko A. N. Kudryavtsev A. A. Lozinskii M. O. 《Russian Journal of Organic Chemistry》2004,40(2):232-238
A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H-1,2,4-triazole-5-thiones. 相似文献
8.
Yoshiko Miyamoto 《Journal of heterocyclic chemistry》2000,37(6):1587-1590
Diaminomethylenehydrazones of cyclic ketones 1–5 reacted with ethyl N‐cyanoimidate (I) at room temperature or with bis(methylthio)methylenecyanamide (II) under brief heating to give directly the corresponding spiro[cycloalkane[1′,2′,4′]triazolo[1′,5′,‐a][1′,3′‐5′]triazine] derivatives 7–12 in moderate to high yields. Ring‐opening reaction of the spiro[cycloalkanetriazolotriazine] derivatives occurred at the cycloalkane moiety upon heating in solution to give 2‐alkyl‐5‐amino[1,2,4]triazolotriazines 13–16. Diaminomethylenehydrazones 17–19, of hindered acyclic ketones, gave 2‐methyl‐7‐methylthio[1,2,4]‐triazolo[1,5‐a][1,3,5]triazines 21–23 by the reaction with II as the main products with apparent loss of 2‐methylpropane from the potential precursor, 2‐tert‐butyl‐2‐methyl‐7‐methylthio[1,2,4]triazolo[1,5‐a]‐[1,3,5]triazines 20, in good yields. In general, bis(methylthio)methylenecyanamide II was found to be a favorable reagent to the one‐step synthesis of the spiro[cycloalkanetriazolotriazine] derivatives from the diaminomethylenehydrazones. The spectral data and structural assignments of the fused triazine products are discussed. 相似文献
9.
Mohammed Loubidi Anaïs Moutardier Joana F. Campos Sabine Berteina-Raboin 《Tetrahedron letters》2018,59(11):1050-1054
A rapid and efficient method is reported for the synthesis of the [1,2,4]triazolo[1,5-a]pyrimidine motif. Palladium catalyzed Suzuki and Sonogashira cross coupling reactions on 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine were performed. The direct sp3 arylation of compounds resulting from the Suzuki reaction was then carried out. 相似文献
10.
G. G. Danagulyan L. G. Sahakyan G. A. Panosyan 《Chemistry of Heterocyclic Compounds》2000,36(2):185-189
The condensation of substituted 2-benzyl-4-hydrazinopyrimidines with phenylpyruvic acid gave the corresponding hydrazones, which cyclize upon the action of POCl, to give derivatives of pyrimido[6,1-c][1,2,4]-triazine. The substituted 2-benzylpyrimidinylhydrazides of some carboxylic acids react with POCl, to give 1,2,4-triazolo[4,3-c]pyrimidines. The reaction of 7-benzyl-5-methyl-l-phenyl-1,2,4-triazolo[2,3-c]pyrimidine with sodium ethylate leads to rearrangement and formation of 7-benzyl-5-methyl-2-phenyl-1,2,4-triazolo[2,3-c]pyrimidine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 225–229, February, 2000. 相似文献
11.
Cevher Altu? Yasar Dürüst Mark C. Elliott Benson M. Kariuki 《Tetrahedron letters》2009,50(34):4919-4986
The reaction of alkylidenepyrrolidines with nitrolic acids gives rise to the formation of novel 3,7a-disubstituted (1,2,4-oxadiazol-5-yl)-5,6,7,7a-tetrahydropyrrolo[1,2-d][1,2,4]oxadiazoles. A plausible mechanism for this reaction is proposed, which features nitrosation of the enamine by the nitrous acid that is liberated from the nitrolic acid. 相似文献
12.
A series of novel 5-amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles were synthesized by a one-pot reaction of 3-amino-1,2,4-triazole, malononitrile and aryl aldehydes in the presence of 20 mol% NaOH in ethanol under heating or ultrasonic irradiation. The structures of the target compounds were confirmed by inspection of their (1)H- NMR, (13)C-NMR, IR and MS spectra. The advantages of this method are short reaction times, good yields, high selectivity and operational simplicity. 相似文献
13.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2005,41(6):782-786
The products of the reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with aryl bromomethyl ketones are 2-aryl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones and aryl methyl ketones or 2,5-diaryl[1,3]thiazolo[3,2-b][1,2,4]triazoles and 3-phenyl-2-propenoic acid, depending on the structure of R. The reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with benzyl bromide yields 5-aryl-3-benzylthio-4H-1,2,4-triazoles and 3-aryl-2-propenoyl bromide.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 905–909, June, 2005. 相似文献
14.
Asier Unciti-Broceta María José Pineda-de-las-Infantas Antonio Espinosa 《Tetrahedron letters》2010,51(17):2262-2264
The synthesis and characterization of five different 9-alkyl-6-amino[1,2,3]triazolo[3,4-c]-5-azaquinoxalines is described. Due to the notable electrophilic character of the C-6 position of the [1,2,4]triazolo[3,4-c]-5-azaquinoxaline tricyclic system, SNAr amination was achieved simply by reacting the corresponding 6-chloro derivative with ammonia-saturated acetonitrile (a non-nucleophilic polar solvent) in a sealed reaction vessel, using microwave-mediated or conventional heating. 相似文献
15.
V. N. Britsun 《Russian Journal of Organic Chemistry》2008,44(10):1528-1531
Reactions of N-aryl-3-oxobutanethioamides with 1H-1,2,4-triazole-5-amine give mixtures of 7-arylamino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidines, 5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-7-thione, 7-methyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-5-thione, and 5-arylamino-7-methyl[1,2,4]triazolo[ 1,5-a]pyrimidines whose ratio depends on the substituent in the aryl group of initial N-aryl-3-oxobutanethioamide and solvent nature (the presence of a proton-donor solvent). 相似文献
16.
Mamdouh A. M. Taha 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2525-2533
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
17.
V. N. Britsun A. N. Borisevich L. S. Samoilenko A. N. Chernega M. O. Lozinskii 《Russian Journal of Organic Chemistry》2006,42(10):1516-1520
Reactions of 3-oxo-N-phenylbutanethioamide with 3-substituted 5-amino-1H-1,2,4-triazoles in acetic acid led to the formation of 5-methyl-7,8-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-7-thiones, 7-methyl-5,8-dihydrol[1,2,4]triazolo[1,5-a]pyrimidine-5-thiones and 7-methyl-5-phenylamino[1,2,4]triazolo[1,5-a]pyrimidines. The structure of the products was proved by the 1H and 13C NMR spectra, X-ray diffraction data, and chemical transformations. 相似文献
18.
AbstractA novel series of bis(tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8-ones) and bis(tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolinones) containing amide linkages were regionselectively prepared via a three-component reaction of bis(aldehydes) with dimedone and 3-amino-1,2,4-triazole (or 2-aminobenzimidazole) under conventional heating as well as under microwave irradiation. 相似文献
19.
The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones was performed. The 2-thioxopyrimidin-4-ones used in the synthesis reacted with hydrazonoyl chlorides in a regioselective manner to produce the angular regioisomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones rather than the linear isomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones. The synthesis process took place with electronic control. The angular regiochemistry of the products was confirmed by X-ray experiments and two-dimensional NMR studies. 相似文献
20.
Vas’kevich R. I. Bentya A. V. Staninets V. I. 《Russian Journal of Organic Chemistry》2010,46(2):286-290
The reaction of 1-(4-oxo-1-R-5H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-arylthiosemicarbazides with methyl iodide gave rise to 1,2,4-triazolo-pyrazolopyrimidinones of linear structure,
and with dicyclohexylcarbodiimide the products had angular and linear structure. The heating of compounds obtained higher
than their melting point resulted in their isomerization into 7-aryl-amino-1-R-1,8-dihydro-4H-pyrazolo[3,4-d]-[1,2,4]triazolo[1,5-a]pyrimidin-4-ones. 相似文献