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1.
V. M. Chernyshev A. N. Sokolov V. A. Taranushich 《Russian Journal of Applied Chemistry》2007,80(10):1691-1694
A procedure for synthesis of 2-sulfonylamino-1,2,4-triazolo[1,5-a]pyrimidines by sulfonylation of 2-amino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines, followed by oxidation of intermediate 2-sulfonylamino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines, was suggested. 相似文献
2.
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
3.
N. I. Zemlyanaya T. M. Karnozhitskaya V. I. Musatov I. S. Konovalova S. V. Shishkina V. V. Lipson 《Russian Journal of Organic Chemistry》2018,54(8):1241-1249
5,5,7-Trimethyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-ol was synthesized by cyclocondensation of 3-amino-1,2,4-triazole with 4-methylpent-3-en-2-one; its chemical transformations, and also the transformations of 5-phenyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-ol were investigated in reactions with reagents of diverse electronic nature. 相似文献
4.
Kh. S. Shikhaliev P. S. Romanov A. S. Shestakov N. V. Stolpovskaya M. Yu. Krysin A. Yu. Potapov A. N. Proshin 《Russian Chemical Bulletin》2016,65(4):1008-1012
A reaction of N-substituted 5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles with dimethylformamide dimethyl acetal gave 3-(5-amino-1,2,4-thiadiazol-3-yl)-4-(dimethylamino)but-3en-2-ones, whose cyclization with hydrazine, guanidine, 1H-pyrazol-5-amines and 6-aminopyrimidin-4(3H)-ones led to 3-methyl-1H-pyrazole, 4-methylpyrimidin-2-amine, 5-methyl3-arylpyrazolo[1,5-a]pyrimidines, and 5-methyl-2-R-pyrido[2,3-d]pyrimidin-4(3H)-ones containing a 5-amino-1,2,4-thiadiazole fragment linearly bound at position 3. 相似文献
5.
S. N. Sirakanyan V. G. Kartsev E. K. Hakobyan A. A. Hovakimyan 《Russian Journal of Organic Chemistry》2018,54(6):923-928
Methods have been developed for the synthesis of new 8-amino-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine starting from 7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile. 8-Hydrazinyl-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine has been converted to isomeric pentacyclic structures with a triazole ring fused through the [c] side of the pyrimidine ring, and their Dimroth rearrangement has been accomplished in both acidic and basic media. New heterocyclic systems containing pyrrolo[1,2-a]pyrimidinone and pyrimido[1,2-a]azepinone fragments were obtained on the basis of the thieno-[2,3-c][2,7]naphthyridine derivative. 相似文献
6.
V. L. Gein L. F. Gein E. P. Tsyplyakova O. S. Panova 《Russian Journal of Organic Chemistry》2007,43(9):1382-1386
6-Acyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylic acids and methyl 6-acyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates were synthesized by fusion of 4-aryl-2,4-dioxobutanoic acids and their methyl esters, respectively, with 1H-tetrazol-5-amine and aromatic aldehydes. The reaction of methyl 2,4-dioxopentanoate with 1H-tetrazol-5-amine and 2-fluorobenzaldehyde in boiling acetic acid gave methyl 6-acetyl-5-hydroxy-7-(2-fluorophenyl)-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidine-5-carboxylate. 相似文献
7.
V. N. Britsun A. N. Borisevich A. N. Esipenko M. O. Lozinskii 《Russian Journal of Organic Chemistry》2007,43(1):103-107
N-Aryl-3-oxobutanethioamides react with 2-amino-1,3-thiazole (2-amino-1,3-benzothiazole) in acetic acid to give mixtures of 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-thione (2-methyl-4H-pyrimido-[2,1-b][1,3]benzothiazole-4-thione) and 5-arylimino-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidines (4-arylimino-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazoles), whose ratio depends on the nature of the aryl substituent in the initial butanethioamide. 相似文献
8.
V. M. Chernyshev A. N. Sokolov V. A. Taranushich 《Russian Journal of Applied Chemistry》2006,79(7):1134-1137
An improved procedure is suggested for preparing 2-amino-1,2,4-triazolo[1,5-a]pyrimidines from 3,5-diamino-1,2,4-triazole and unsaturated aromatic ketones, with acetyl protection of the amino group in the step of oxidation of 2-amino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines. 相似文献
9.
Maksim A. Kolosov Elena H. Shvets Dmitriy A. Manuenkov Sergey A. Vlasenko Irina V. Omelchenko Svetlana V. Shishkina Valeriy D. Orlov 《Tetrahedron letters》2017,58(12):1207-1210
6-Unsubstituted 7-R-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines (R = H or Me) were synthesized via two pathways: (a) deacylation of the corresponding 5-acetyl Biginelli-like precursors in KOH/H2O and (b) reduction of the corresponding 1,2,4-triazolo[1,5-a]pyrimidines using LiAlH4. The products could be easily formylated at position 6, which is promising for the further synthesis of functionalized 6-substituted derivatives of 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines. In contrast, 6-acetyl-7-(4-(N,N-dimethylaminophenyl))-5-methyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine undergoes a cascade process in KOH/H2O, leading to the formation of a 4,5,8,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazoline derivative. 相似文献
10.
V. V. Lipson T. M. Karnozhitskaya S. V. Shishkina O. V. Shishkin A. V. Turov 《Russian Journal of Organic Chemistry》2008,44(11):1695-1707
Reaction of 5-amino-3-methylpyrazole, 3-amino-, 5-amino-3-methylsulfanyl-1,2,4-triazole and 5-amino-1,2,4-triazole-3-thione with 3-phenylacryloyl-chloride under mild conditions is characterized by low selectivity and does not lead to the formation of fused heterocyclic systems but gives mixtures of products of mono- and diacylation of the nucleophilic sites in the molecules of α-aminoazoles. Endocyclic monoacyl derivatives of aminotriazoles in DMF undergo a transacylation at the exo-amino-group followed by cyclization into dihydro-1,2,4-triazolo[1,5-a]-pyrimidin-5-ones. 相似文献
11.
V. V. Lipson S. M. Desenko V. V. Borodina M. G. Shirobokova T. M. Karnozhitskaya V. I. Musatov S. V. Kravchenko 《Chemistry of Heterocyclic Compounds》2005,41(2):216-220
The cyclocondensation of methylcinnamates and arylidene derivatives of Meldrums acid with 3-amino-5-methylthio-1,2,4-triazole in DMF gives 2-methylthio-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]-pyrimidin-5-ones. The reaction involving arylidene derivatives of Meldrums acid or its synthetic equivalents in ethyl acetate with a catalytic amount of pyridine gives a mixture of 2-methylthio-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidin-5- and -7-ones.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 246–251, February, 2005. 相似文献
12.
A. A. Moroz V. E. Zhulanov M. V. Dmitriev D. N. Babentsev A. N. Maslivets 《Russian Journal of Organic Chemistry》2018,54(5):780-784
1H-pyrrol-2,3-diones react with nitrones affording substituted pyrrolо[3,2-d]isoxazoles. The structures of ethyl (3R*,3aR*,6aR*)-6-benzyl-3-(4-bromophenyl)-4,5-dioxo-2,6a-diphenylhexahydro-3aHpyrrolo[ 3,2-d]isoxazole-3a-carboxylate and dimethyl (3R*,3aR*,6aS*)-3-(4-bromophenyl)-4,5-dioxo-2,6-diphenyltetrahydro-3aH-pyrrolo[3,2-d]isoxazole-3a,6a(4H)-dicarboxylate were proved by single-crystal X-ray analysis. 相似文献
13.
Brigitte Bouteau Jean-Charles Lancelot Max Robba 《Journal of heterocyclic chemistry》1990,27(6):1649-1651
The synthesis of 1,2,4-triazolo[4,3-a] and [2,3-a]pyridines 7, 8 was achieved by cyclization of 2-hydrazino-8-nitropyridine 3a with formic acid. The 4,5,6,7-tetrahydro-1,2,4-triazolo[2,3-a]pyridine 13 and 8-amino-1,2,4-triazolo[2,3-a]pyridine 9 were obtained by catalytic hydrogenation. The reduction of triazolo pyridine 8 using stannous chloride led to the intermediate compound 10 which with acetic anhydride afforded 8-acetylamino-5-chloro-1,2,4-triazolo[2,3-a]pyridine 10a . The structure of the derivatives was determined by 1H-nmr (DMSO-d6). 相似文献
14.
V. V. Lipson T. M. Karnozhitskaya S. M. Desenko S. V. Shishkina O. E. Shishkin V. I. Musatov 《Russian Journal of Organic Chemistry》2007,43(2):249-255
Cyclocondensations of diethyl benzylidenemalonate with 3-amino-5-methylpyrazole, 3,5-diamino-1,2,4-triazole, 3,4,5-triamino-1,2,4-triazole, and 2-amino-benzimidazole in alcohols take a single route and lead to the formation of functionally substituted partially hydrogenated pyrazolo-, triazolo[1,5-a]-pyrimidin-5-ones and pyrimido[1,2-a]benzimidazol-2-one respectively. From reaction mixtures involving 3-amino-1,2,4-triazole and its 5-methylsulfanyl analog in methanol the intermediate products of heterocyclization were isolated forming as a result of alkylation with the β-carbon of the unsaturated ester the endocyclic nucleophilic sites of aminoazoles. The structure of one among the products obtained, diethyl(3-amino-5-methylsulfanyl-1,2,4-triazol-2-yl)benzylmalonate was proved by X-ray crystallography. In DMF the same reagents yielded mixtures of partially hydrogenated triazolo[1,5-a]pyrimidin-5-ones. 相似文献
15.
S. O. Kasatkina E. E. Stepanova M. V. Dmitriev A. N. Maslivets 《Russian Journal of Organic Chemistry》2018,54(10):1515-1518
Hetero-Diels–Alder reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with styrene afforded diastereoisomeric (5R*,6aR*)- and (5S*,6aR*)-3,5-diaryl-5,6-dihydropyrano[4′,3′:2,3]pyrrolo[1,2-a]-quinoxaline-1,2,7(8H)-triones. 相似文献
16.
Thermally induced [4 + 2]-cycloaddition of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with alkyl vinyl ethers afforded mixtures of diastereoisomeric (5S*,6aR*)- and (5R*,6aR*)-5-alkoxy-3-aryl-5,6-dihydropyrano[ 4′,3′: 2,3]pyrrolo[1,2-a]quinoxaline-1,2,7(8H)-triones. 相似文献
17.
Treatment of 1,2,4-triazoles (1) with diethylmalonate in bromobenzene gave 1,2,4-triazolo-[1,5-a]pyridines 2. Chlorination of 2 using POCl3/DMF (Vilsmeier reagent) led to the isolation of 7-chloro-6-formyl-1,2,4-triazolo[1,5-a]pyridine derivative 4, which reacted with the stabilized ylid 5 to afford 6-ethoxycarbonylvinyl-1,2,4-triazolo[1,5-a]-pyridines 6. Azidation of 6 yielded the corresponding azido compound 7, (Scheme 2). Reduction of 7 with Na2S2O4 gave the corresponding 7-amino compound 8, which cyclized in boiling DMF to give the novel 1,2,4-triazolo[1,5-g][1,6]naphthyridines 9. On the other hand, reacting 7 with one equivalent of PPh3 (aza-Wittig reaction) in CH2Cl2 gave 7-imino-phosphorane derivative 10, and subsequent cyclization in boiling DMF afforded the new 1,2,4-triazolo[1,5-g][1,6]naphthyridine derivative 11 (Scheme 3). However, treatment of 10 with phenyl isothiocyanate in 1,2-dichlorobenzene at reflux temperature gave the new 1,2,4-triazolo[1,5-g][1,6]naphthyridine derivative 14 (Scheme 4). Refluxing 6 with excess of a primary amines 15a,b in absolute. EtOH yielded the corresponding 7-alkyl-amino-1,2,4-triazolo[1,5-a]pyridines 16a,b. These obtained amines 16a,b underwent intramolecular heterocyclization in boiling DMF to give the novel 9-alkyl-1,2,4-triazolo[1,5-g][1,6]-naphthyridines 17a,b, in excellent yields (Scheme 5). 相似文献
18.
K. V. Savateev E. N. Ulomsky V. L. Rusinov M. L. Isenov O. N. Chupakhin 《Russian Chemical Bulletin》2015,64(6):1378-1384
A universal method was developed for the synthesis of 7-alkylamino-6-nitro-1,2,4-triazolo-[1,5-a]pyrimidines by the chlorodeoxygenation of the corresponding triazolopyrimidones. 相似文献
19.
M. V. Pryadeina Ya. V. Burgart V. I. Saloutin P. A. Slepukhin E. V. Sadchikova E. N. Ulomskii 《Russian Journal of Organic Chemistry》2009,45(2):242-247
Methods were developed of the synthesis of alkyl 2-hydroxy-2-fluoroalkyl-4-phenyl-1,2,3,4—tetrahydroimidazo-[1,5-a]pyrimidine-3-carboxylates and alkyl-5-hydroxy-2,7-diphenyl-5-fluoroalkyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-6-carboxylates by regioselective [3+3]-cycloaddition of 5-aminoimidazole or 5-aminopyrazole to alkyl 2-benzylidene-3-oxo-3-fluoroalkylpropionates at the fluoroacylvinyl fragment. 相似文献
20.
Pryadeina M. V. Burgart Ya. V. Saloutin V. I. Kodess M. I. Ulomskii E. N. Rusinov V. L. 《Russian Journal of Organic Chemistry》2004,40(6):902-907
Fluorinated 3-oxo esters react with aldehydes and 3-amino-1,2,4-triazoles and 5-aminotetrazoles to give, respectively, 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-triazolo[1,5-a]pyrimidines and -tetra-zolo[1,5-a]pyrimidines. The same heterocyclic products can be obtained by reaction of 2-benzylidene-2-fluoroacyl esters with the corresponding aminoazoles. 相似文献