共查询到20条相似文献,搜索用时 31 毫秒
1.
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
2.
E. M. El-Telbani R. H. Swellem G. A. M. Nawwar 《Russian Journal of Organic Chemistry》2007,43(12):1815-1820
Condensation of 4-amino-4H-1,2,4-triazole-3-thiol and 4-amino-6-methyl-3-sulfanyl-1,2,4-triazin-5(4H)-one with ethyl cyanoacetate gave ethyl [1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylacetate and ethyl 3-methyl-4-oxo-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-7-ylacetate, respectively. Reactions of the condensation products with 1,3-diphenylprop-2-en-1-one, aromatic
aldehydes, and carbon disulfide or N,N-dimethylformamide dimethyl acetal (followed by treatment with hydrazine hydrate) gave the corresponding 6-hetaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and 7-hetaryl-3-methyl-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-ones. Preliminary tests revealed fungicidal activity of the pyrazolyl-substituted derivatives.
Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 12, pp. 1813–1818.
The text was submitted by the authors in English. 相似文献
3.
Gundurao Kolavi 《Tetrahedron letters》2006,47(16):2811-2814
Novel heterocyclic systems 2-alkyl/aryl-9-(2-hydroxybenzylidene)-7,9-dihydro-8H-[1,3,4]thiadiazolo[2′,3′:2,3]imidazo[4,5-d][1,2]diazepin-8-one and 9-(2-hydroxy-benzylidene)-3,3-dimethyl-3,4,7,9-tetrahydro-2H-11-thia-4b,6,7,10-tetraazaindeno[1,2-a]azulene-1,8-dione are synthesized via an intramolecular amidation reaction. An interesting ring opening and cyclization of 2-alkyl/aryl-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde and 6,6-dimethyl-8-oxo-2-(2-oxo-2H-chromen-3-yl)-5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzothiazole-3-carbaldehyde are discussed. 相似文献
4.
Demchenko A. M. Yanchenko V. A. Lozinskii M. O. 《Russian Journal of Organic Chemistry》2003,39(7):1025-1028
Starting from 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols and substituted chloroacetanilides, the corresponding (5-alkyl-4-amino-4H-1,2,4-triazol-3-ylsulfanyl)acetanilides were synthesized. The products underwent intramolecular cyclization in boiling phosphoryl chloride to afford 3-alkyl-6-arylamino-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazines. 3-Alkyl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hydrobromides were obtained by reaction of 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols with substituted phenacyl bromides. 相似文献
5.
V. S. Matiichuk M. A. Potopnyk N. D. Obushak 《Russian Journal of Organic Chemistry》2009,45(5):712-718
The reaction of ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate with the malonic acid led to the formation (2E)-3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid. In reactions of this acid chloride with 4-amino-5-aryl(hetaryl)-4H-1,2,4-triazole-3-thiols were obtained ethyl 4-[(E)-2-{3-aryl(hetaryl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl}ethenyl]-1-phenyl-1H-pyrazoe-3-carboxylates, with 5-aryltetrazoles, ethyl 4-[(E)-2-(5-aryl-1,3,4-oxadiazol-2-yl)-ethenyl]-1-phenyl-1H-pyrazole-3-carboxylates, with 1-(2-hydroxy-3,5-dimethylphenyl) followed by the Baker-Venkataraman rearrangement and the cyclization, ethyl 4-[(E)-2-(6,8-dimethyl-4-oxo-4Hchromen-2-yl)ethenyl]-1-phenyl-1H-pyrazole-3-carboxylate. 相似文献
6.
E. V. Nosovoa G. N. Lipunova A. A. Laeva L. P. Sidorova V. N. Charushin 《Russian Journal of Organic Chemistry》2007,43(1):68-76
Fluorinated derivatives of 4H-1,3-benzothiazin-4-one, [1,2,4]triazolo[4,3-a]pyrimidine, [1,2,4]triazolo[3,4-b][1,3]benzazoles, and 1,5-dihydro-1,2,4-triazole-5-thione were synthesized by addition of hydrazines and their derivatives to tetrafluorobenzoyl isothiocyanate, followed by cyclization of intermediate thiosemicarbazides. 相似文献
7.
Navabeh Nami Masoumeh Hosseinzadeh Ehteram Rahimi 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2438-2442
The reaction of 4-oxo-2-(2-oxo-1,2-dihydroindol-3-ylidene)hydrazone-1,3-thiazin-6-methyl carboxylate 2 with hydrazine hydrate in methanol gave 4-oxo-2-(2-oxo-1,2-dihydroindol-3-ylidene)hydrazone-1,3-thiazin-6-carbonylhydrazine 3. Furthermore, the reaction of 3 with carbon disulfide and then hydrazine hydrate afforded 3-[6-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4-oxo-1,3-thiazin-2-yl] hydrazone-1,3-dihydroindol-2-one 5. the latest reacted with DMAD to give {6-hydroxy-3-[4-oxo-2-(2-oxo-1,2-dihydroindol-3-ylidene)hydrazone-1,3-thiazin-6yl]-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene}methoxycarbonylmethylene 6. 相似文献
8.
1,3-Dialkyl-5-amino-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones reacted with acetylacetone to give the corresponding 4-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5-ylamino)pent-3-en-2-ones which underwent intramolecular cyclization to 1,3-dialkyl-5,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]-[1,8]naphthyridin-2-ones on heating in polyphosphoric acid or diphenyl ether. Analogous reaction of 1,3-dialkyl-5-amino-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones with ethyl acetoacetate led to the formation of ethyl 3-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5-ylamino)but-2-enoates whose cyclization afforded 1,3-dialkyl-8-hydroxy-7-methyl-1,3-dihydro-2H-imidazo[5,4-b][1,8]naphthyridin-2-ones. 相似文献
9.
Andrey V. Khramchikhin Mariya A. Skrylnikova Iana L. Esaulkova Ekaterina O. Sinegubova Vladimir V. Zarubaev Maxim A. Gureev Aleksandra M. Puzyk Vladimir A. Ostrovskii 《Molecules (Basel, Switzerland)》2022,27(22)
This study of the interaction system of binucleophilic 3-substituted 4-amino-4H-1,2,4-triazole-5-thiols and 3-phenyl-2-propynal made it possible to develop a new approach to synthesis of such isomeric classes as 7-benzylidene-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine and 8-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine. Among the 20 compounds studied in vitro against influenza A/Puerto Rico/8/34 (H1N1) virus, half of them demonstrated selectivity index (SI) of 10 or higher and one of them (4-((3-phenylprop-2-yn-1-yl)amino)-4H-1,2,4-triazole-3-thiol) possessed the highest (SI > 300). Docking results and values showed that the preferred interactant for our ligands was M2 proton channel of the influenza A virus. Protein-ligand interactions modeling showed that the aliphatic moiety of ligands could negatively regulate target activity level. 相似文献
10.
A novel series of 1-(1-carbonylmethyl-1H-benzotriazole) thiosemicarbazides 3a-e was synthesized and then cyclized with sodium hydroxide to afford 1-(4-substituted-4H-1,2,4-triazole-3-thion-5-yl)methyl-1H-benzotriazoles 4a-e , which were alkylated with ethyl iodide to l-(3-ethylthio-4-substituted-4H-1,2,4-triazol-5-yl)-methyl-1H-benzotriazoles 5b-e . The reaction of 1H-benzotriazol-1-acetic acid hydrazide ( 2 ) with carbon disulphide and potassium hydroxide followed by hydrazine hydrate gave 1-(4-amino-4H-1,2,4-triazole-3-thion-5-yl)methyl-1H-benzotriazole ( 6 ). Its subsequent condensation with carboxylic acids in the presence of phosphorus oxychloride or with phenacyl bromides afforded two series of fused heterocycles namely; 6-substituted-3-[1-(1H-benzotriazole)methyl]-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 7a-e and 6-substituted phenyl-3-[1-(1H-benzotriazole)methyl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 8a-e respectively. The structure of the newly synthesized compounds was elucidated by elemental analyses, ir and nmr spectra. 相似文献
11.
Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N??-dicyclohexylcarbodiimide with formation of 3-[6-aryl-4-oxo-3-cyclohexyl-2-cyclohexylimino-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-ones. Thermolysis of the latter is accompanied by elimination of N,N??-dicyclohexylcarbodiimide, and aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes thus generated undergo cyclodimerization to produce 7-aroyl-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl benzoates. 相似文献
12.
N. D. Obushak N. T. Pokhodylo I. I. Krupa V. S. Matiichuk 《Russian Journal of Organic Chemistry》2007,43(8):1223-1227
4-Amino-5-R1-4H-1,2,4-triazole-3-thiols react with 2-R2-6-R3-quinoline-4-carboxylic acids in phosphoryl chloride to give 2-R2-6-R3-4-(3-R1-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)quinolines. 相似文献
13.
Yoshihisa Kurasawa Atsushi Satoh Satoyuki Ninomiya Harumi Arai Kiyoko Arai Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(4):1229-1231
The reaction of the quinoxaline 1 with 4-ethoxycarbonyl-1H-pyrazole-5-diazonium chloride 7 at room temperature gave 3-[α-(4-ethoxycarbonyl-1H-pyrazol-5-ylhydrazono)methoxycarbonylmethyl]-2-oxo-1,2-dihydroquinoxaline 8. The pmr spectrum of 8 in deuteriodimethylsulfoxide supported the presence of two tautomers 8-I and 8-II. Refluxing of 8 in N,N-dimethylformamide or acetic acid resulted in cyclization to afford 8-ethoxycarbonyl-4-oxo-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine 9. Compound 9 was also obtained directly by the reaction of 1 with 7 under reflux in better yield. The reaction of 9 with hydrazine hydrate provided the hydrazinium salt 10 , while the reactions of 9 with triethyl and trimethyl orthoformates in the presence of 1,8-diazabicyclo[5,4,0]-7-undecene produced 8-ethoxycarbonyl-4-ethoxyl-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)pyrazolo[5,1-c][1,2,4]triazine 11a and 8-ethoxycarbonyl-4-methoxyl-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)pyrazolo[5,1-c][1,2,4]triazine 11b , respectively. The chlorination of 11a with phosphoryl chloride gave 3-(3-chloroquinoxalin-2-yl)-8-ethoxycarbonyl-4-ethoxylpyrazolo[5,1-c]-[1,2,4]triazine 12 , whose reaction with morpholine afforded 8-ethoxycarbonyl-4-ethoxyl-3-[3-(morpholin-4-yl)-quinoxalin-2-yl]pyrazolo[5,1-c][1,2,4]triazine 13. 相似文献
14.
L. M. Mironovich M. V. Kostina A. V. Bozhok 《Russian Journal of Organic Chemistry》2012,48(9):1226-1228
Treatment of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate with P2S5 in pyridine gave ethyl 7-amino-3-tert-butyl-4-thioxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate which was subjected to acylation, decarboxylation, and hydrazinolysis. 相似文献
15.
Yu. N. Oludina S. V. Bukharov A. R. Burilov R. G. Tagasheva V. V. Syakaev R. Z. Musin E. F. Akhmetova G. N. Nugumanova 《Russian Chemical Bulletin》2014,63(1):115-117
Addition of isatin to the exocyclic double bond of dimethyl (3,5-di-tert-butyl-4-oxocyclohexa-2,5-dienylidene)methylphosphonate gave dimethyl (3,5-di-tert-butyl-4-hydroxyphenyl)(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)methylphosphonate. Its subsequent functionalization in reactions with thiosemicarbazide and 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionohydrazide yielded isatin derivatives containing several pharmacophoric fragments. 相似文献
16.
Angelina N. Kravchenko Sergei V. Vasilevskii Galina A. Gazieva Vladimir V. Baranov Valery A. Barachevsky Olga I. Kobeleva Olga V. Venidiktova Valentina A. Karnoukhova 《Tetrahedron》2018,74(19):2359-2368
For the first time 5,7-di-tert-butyl-1,3-dimethyl-3a,9a-diphenyl-3,3a-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-d]imidazol-2(9aH)-one 13 and complex 9 of 4,6-di-tert-butyl-3-nitrobenzene-1,2-diol with 1,3-dimethyl-4,5-diphenyl-1H-imidazol-2(3H)-one 10a were prepared by the reactions of 3-alkylthio-5,7-dimethyl-4a,7a-diphenyl-4a,5,7,7a-tetrahydro-1H-imidazo[4,5-e]-1,2,4-triazin-6(4H)-ones with 3,5-di-tert-butyl-1,2-benzoquinone 1 and 4,6-di-tert-butyl-3-nitro-1,2-benzoquinone 2, respectively. Photochemical transformations of compounds 9 and 10a as well as products of its photooxygenation involving singlet oxygen under UV irradiation: urea 16, isomeric 1,3-dimethyl-4,5-diphenylimidazolidin-2-ones 17 and 17′, and compound 18 were studied by the spectral-kinetic method. Data on the absorption and fluorescence properties of synthesized compounds and their photoproducts were obtained. 相似文献
17.
N. V. Gorbulenko T. M. Tkachuk T. V. Shokol V. V. Semeniuchenko A. V. Turov V. P. Khilya 《Chemistry of Heterocyclic Compounds》2007,43(5):569-575
The interaction has been studied of a series of substituted 3-hetaryl-7-hydroxychromones with amino acids and formaldehyde
(reactants ratio 1: 1: 2 respectively). In the case of glycine and Het = 3-isoxazolyl the product of aminomethylation at position
8 of the chromone was obtained, and with other Het (including Het = 4-phenyl-1,2,4-triazol-3-yl) 2-[6-alkyl-3-hetaryl-4-oxo-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-9-yl]acetic
acids were formed. With β-alanine and Het = 4-phenyl-1,2,4-triazol-3-yl the corresponding β-substituted propionic acid was
synthesized, but proline did not participate in the reaction, leading to bis(6-ethyl-3-hetaryl-7-hydroxychromon-8-yl)methane.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 683–689, May, 2007. 相似文献
18.
Reactions of 3-Z-aroylmethylene-6-chloro-3,4-dihydro-2H-1,4-benzoxazine-2-ones with oxalyl chloride afford 3-aroyl-8-chloro-1,2-dihydro-4H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones and Z-3-(2-aryl-2-chlorovinyl)-6-chloro-2H-1,4-benzoxazine-2-ones. Aroyl(imidoyl)ketenes generated by decarbonylation of pyrrolobenzoxazinetriones undergo dimerization through [4+2]-cycloaddition to form 4-aroyl-3-aroyloxy-2-(2-oxo-2H-1,4-benzoxazin-3-yl)-1H, 5H-pyrido[2,1-c][1,4]benzoxazine-1,5-diones. 相似文献
19.
Monika Kowalewska 《Tetrahedron》2008,64(22):5085-5090
2-Alkyl-7-methoxy-5-nitrobenzo[b]furan, 2-alkyl-9-methoxy-7-nitro-3-oxo-2,3-dihydro-5H-benzo[e][1,4]-dioxepin-5-yl acetate and 2-alkyl-5-hydroxy-9-methoxy-7-nitro-5H-benzo[e][1,4]-dioxepin-3-one were formed as a result of the cyclization of 2-(2-formyl-6-methoxy-4-nitrophenoxy)alkanoic acids under classical Perkin reaction conditions. The products were characterized by spectroscopic methods and the mechanism of the cyclization is discussed. 相似文献
20.
V. A. Mamedov L. V. Mustakimova A. T. Gubaidullin I. A. Litvinov Ya. A. Levin 《Russian Journal of Organic Chemistry》2004,40(9):1309-1317
4-Amino-3-(2-R-5-phenylthiazol-4-yl)-1,2,4-triazole-5-thiones react with methyl 3-chloro-2-oxo-3-phenylpropionate to give methyl 3-(2-R-5-phenylthiazol-4-yl)-7-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-6-carboxylates. According to the X-ray diffraction data, the thiazole ring in the products is planar, while the thiadiazine ring has a distorted unsymmetrical boat conformation. Depending on the substituent in the thiazole ring, methyl 3-(2-R-5-phenylthiazol-4-yl)-7-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-6-carboxylates in crystal give rise to different supramolecular structures, lamellar and cylindrical.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1358–1365.Original Russian Text Copyright © 2004 by Mamedov, Mustakimova, Gubaidullin, Litvinov, Levin. 相似文献