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1.
Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles 总被引:1,自引:0,他引:1
Methods for the synthesis of amino(1,2,3-triazol-1-yl)-1,2,5-oxadiazoles (amino-triazolylfurazans) with CH2Cl and COCH2Br substituents in the triazole ring were developed and nucleophilic substitution for their halogen atom in reactions with
N-, O-, and S-nucleophiles were studied. The possibility of displacing the NO2 group from the furazan and triazole rings in triazolylfurazans by an azido group was investigated. Novel compounds of this
series were synthesized; the reaction rate and pathway were found to depend on the nature of the substrate and the reagent
and the position of the substituent in isomers.
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1866–1876, August, 2005. 相似文献
2.
V. V. Shchepin M. I. Kodess Yu. Kh. Sazhneva N. Yu. Russkikh 《Russian Journal of General Chemistry》2005,75(10):1622-1627
Ethyl esters of 2,4-dibromo-2-R1-4-R2-3-oxopentanoic and -hexanoic acids react with zinc and aliphatic or aromatic aldehydes under the conditions of the Reformatskii reaction to give 3-R1-5,5-R2, R2-6-R3-2,3,5,6-tetrahydropyran-2,4-diones, which are obtained in three forms: keto, enol with enolization of the keto group, and enol with enolization of the ester group. The keto form is isolated by crystallization from a mixture of CCl4 and petroleum ether; the first enol form, from MeOH, EtOH, and polar aprotic solvents; and the second enol form, from CHCl3. The second enol form is oxidized in DMSO to form a keto compound containing a hydroxy group at the 3-position of the heteroring. 相似文献
3.
N. D. Obushak N. T. Pokhodylo N. I. Pidlypnyi V. S. Matiichuk 《Russian Journal of Organic Chemistry》2008,44(10):1522-1527
5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N′-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N′-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles. 相似文献
4.
L. V. Batog V. Yu. Rozhkov E. V. Shatunova M. I. Struchkova 《Russian Chemical Bulletin》2008,57(1):165-169
Methods for the synthesis of 4-amino-4′-R-3,3′-(NNO)-azoxy-1,2,5-oxadiazoles (amino-azoxyfurazans) with 4-nitro-1,2,3-triazol-1-yl
and 1,2,3-triazolo[4,5-c]furazan-5-yl substituents (R) by cycloaddition of morpholinonitroethylene to 4′-amino-4-azido-3,3′-(ONN)-azoxyfurazan or
oxidative condensation of 3-R-4-aminofurazans with 4-trifluoroacetylamino-3-nitrosofurazan were elaborated. Related polycyclic
azo derivatives were also synthesized.
For preliminary communication, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 159–163, January, 2008. 相似文献
5.
A. Yu. Tyurin O. Yu. Smirnov A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2009,58(2):361-365
An unusual cascade of S
NAr reactions was discovered in the series of benzo-1,2,3,4-tetrazine 1,3-dioxides containing two adjacent nucleofuges X and
Y in the benzene ring. First, the 1,2,3-triazole anion displaces the anion Xs- from the more reactive site. Then the nucleo-phile Xs- displaces the adjacent group Y. For instance, 1,2,3-triazole reacts with 6-azido-5-nitrobenzotetrazine 1,3-dioxide to give
5-azido-6-(1,2,3-triazol-2-yl)benzotetrazine 1,3-dioxide, with 8-azido-7-nitrobenzotetrazine 1,3-dioxide to give 7-azido-8-(1,2,3-triazol-2-yl)benzotetrazine
1,3-dioxide and 7-azido-8-(1,2,3-triazol-1-yl)benzotetrazine 1,3-dioxide, and with 7-bromo-6-(phenylthio)benzotetrazine 1,3-dioxide
to give 7-phenylthio-6-(1,2,3-triazol-2-yl)benzotetrazine 1,3-dioxide. 相似文献
6.
A. A. Medzhidov P. A. Fatullaeva S. M. Peng R. G. Ismaiylov G. H. Lee S. R. Garaeva 《Russian Journal of Coordination Chemistry》2012,38(2):126-133
Reactions of N-(2-hydroxy-3,5-R1,R2-benzyl)-4-aminoantipyrines with copper acetate in ethanol gave complexes with Schiff bases (SBs) rather than the expected
complexes with reduced SBs; i.e., the starting ligands undergo oxidative dehydrogenation during the complexation reaction.
The corresponding complexes with reduced SBs were obtained from sodium salts of the ligands and cupric sulfate in aqueous
solutions. Kinetic measurements showed that oxidative dehydrogenation occurs in the heteroleptic complexes Cu(L
i
)(CH3COO)(X) (L
i
H are derivatives of N-(2-hydroxy-3,5-R1,R2-benzyl)-4-aminoantipyrines; i = 6–10; X = H2O, CH3OH, CH3CH2OH) but does not occur in the complexes CH3OH, CH3CH2OH. The absence of oxidative dehydrogenation of the ligands in Cu(L
i
)2 · H2O can be explained by the octahedral environment of the Cu2+ ion and, accordingly, the absence of the coordination site for molecular oxygen. The molecular structures of two Cu(II) complexes
with SBs were determined by X-ray diffraction. 相似文献
7.
Nazariy T. Pokhodylo Roman D. Savka Olga Ya. Shyyka Mykola D. Obushak 《Journal of heterocyclic chemistry》2020,57(7):2969-2976
The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “click” reaction, with alkynes, in the presence of CuI was studied. The utility of newly synthesized 2-(azidomethyl)-1,3,4/1,2,4-oxadiazoles and chloromethyl-1,3,4/1,2,4-oxadiazole derivatives was explored, and their limitations were determined. Novel 5-([4-aryl-1H-1,2,3-triazol-1-yl]methyl)-3-(aryl)-1,2,4-oxadiazoles, 2-([4-aryl-1H-1,2,3-triazol-1-yl]methyl)-5-(aryl)-1,3,4-oxadiazoles were obtained in good yields. 相似文献
8.
V. V. Shchepin D. V. Fotin M. I. Vakhrin S. N. Shurov 《Russian Journal of General Chemistry》2004,74(9):1406-1409
The Reformatskii reagents formed from alkyl esters of -bromoacetic, -bromopropanoic, and -bromoisobutyric acids and zinc react with N-arylamides of 2-oxochromene-3-carboxylic acid, yielding 3-R1-1-R2-1-R3-4a,10b-dihydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 9, 2004, pp. 1516–1519.Original Russian Text Copyright © 2004 by Shchepin, Fotin, Vakhrin, Shurov.This revised version was published online in April 2005 with a corrected cover date. 相似文献
9.
Godovikova T. I. Vorontsova S. K. Konyushkin L. D. Firgang S. I. Rakitin O. A. 《Russian Chemical Bulletin》2010,59(2):483-485
A number of 3-methyl-4-(5-R-1H-1,2,4-triazol-3-yl)-1,2,5-oxadiazoles were obtained in high yields by thermal dehydration of acylated 4-methyl-1,2,5-oxadiazole-3-carboxamide
hydrazones. 相似文献
10.
Romanova T. V. Mel'nikova S. F. Tselinskii I. V. 《Russian Journal of Organic Chemistry》2003,39(4):574-578
By 1,3-dipolar addition of 1-azido(4-amino-1,2,5-oxadiazol-3-yl)aldoxime to propargyl alcohol and phenylacetylene bicyclic 4-amino-1,2,5-oxadiazol-3-yl(4-R-1,2,3-triazol-1-yl)ketoximes were obtained which in reaction with acetic anhydride afforded the corresponding O-acyl derivatives. Diazotization of 4-amino-1,2,5-oxadiazol-3-yl(4-R-1,2,3-triazol-1-yl)ketoximes furnished 4-azido derivatives. The treatment of 4-amino-1,2,5-oxadiazol-3-yl(4-hydroxymethyl-1,2,3-triazol-1-yl)ketoxime with SOCl2 resulted in 4-amino-1,2,5-oxadiazol-3-yl(4-chloromethyl-1,2,3-triazol-1-yl)ketoxime, whose chlorine atom was readily replaced by azide ion affording 4-amino-1,2,5-oxadiazol-3-yl(4-azidomethyl-1,2,3-triazol-1-yl)ketoxime. 相似文献
11.
B. A. Shainyan V. I. Meshcheryakov I. V. Sterkhova 《Russian Journal of Organic Chemistry》2016,52(7):1032-1035
Three-component heterocyclizations of trifluoro-N-(prop-2-yn-1-yl)methanesulfonamide, trifluoro-N-pheny-N-(prop-2-yn-1-yl)methanesulfonamide, and trifluoro-N,N-di(prop-2-yn-1-yl)methanesulfonamide with formaldehyde and sodium azide afforded N-{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}-, N-{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}-N-phenyl-, and N,N-bis{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}trifluoromethanesulfonamides as the major products together with minor 1-(hydroxymethyl)-1H-1,2,3-triazole isomers. 相似文献
12.
N. T. Pokhodylo O. Ya. Shiika V. S. Matiichuk N. D. Obushak 《Russian Journal of Organic Chemistry》2010,46(3):417-421
2-, 3-, and 4-[5-(1-Aryl-5-R-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines were synthesized from the corresponding 1-aryl-5-R-1H-1,2,3-triazole-4-carbonyl chlorides and 2-, 3-, and 4-(1H-tetrazol-5-yl)-pyridines. 相似文献
13.
V. N. Britsun A. N. Borisevich V. B. Pirozhenko M. O. Lozinskii 《Russian Journal of Organic Chemistry》2007,43(2):276-279
Direction of a reaction between 3-oxo-3-R1-N-R2-propanethioamides and 2-amino-5-R-pyridines in acetic acid depends on the structure of initial thioamides: at R1 = Me, R2 = Ar, Et 2-methyl-7-R-4H-pyrido[1,2-a]-pyrimidine-4-thiones are obtained, and at R1 = Ar, R2 = Me form 1-methyl-5-(N-methylaminothiocarbonyl)-4,6-diaryl-1,2-dihydropyridine-2-thiones. 相似文献
14.
V. S. Matiichuk N. D. Obushak V. M. Tsyalkovskii 《Russian Journal of Organic Chemistry》2005,41(7):1050-1054
Meerwein reactions of arenediazonium bromides with methyl and ethyl acrylates gave 3-aryl-2-bromopropionic acid esters which were subjected to cyclocondensation with N-(2-pyridyl)- and N-(6-methyl-2-pyridyl) thioureas to obtain 5-R1-benzyl-2-(R2-2-pyridylimino)thiazolidin-4-ones. The latter were shown to exist in solution as E isomers of the imino form.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 1071–1075.Original Russian Text Copyright © 2005 by Matiichuk, Obushak, Tsyalkovskii. 相似文献
15.
N. T. Pokhodylo R. D. Savka V. S. Matiichuk N. D. Obushak 《Russian Journal of General Chemistry》2009,79(2):309-314
By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] ethanones (VIIa-VIIe) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids (IIIa–IIIe) and 2-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids (IXa, IXb), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) readily transform into [5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] acetic acids (IVa–IVc) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4H-1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole (VI).
Original Russian Text ? N.T. Pokhodylo, R.D. Savka, V.S. Matiichuk, N.D. Obushak, 2009, published in Zhurnal Obshchei Khimii,
2009, vol. 79, no. 2, pp. 320–325. 相似文献
16.
The structures of paramagnetic complexes CuCl2?L with L = HetCH2Si(OCH2CH2)3N [Het = pyrrol-1-yl (1), indol-1-yl (2), carbazol-9-yl (3), imidazole-1-yl (4), 3,5-dimethylpyrazol-1-yl (5), 1,2,4-triazol-1-yl (6), benzimidazol-1-yl (7), and 1,2,3-benzotriazol-1-yl (8)] were studied by the ESR and quantum chemical methods in terms of the density functional theory (DFT) approximation. The difference in structures of complexes CuCl2?1—CuCl2?8 is mainly determined by the nature of the five-membered heterocycle. The ESR spectra at room temperature are typical of the mononuclear complexes of CuII of axial symmetry with various types of distortions. In complexes CuCl2?1—CuCl2?3, narrow symmetric signals of zero-valent copper are recorded. These signals remain in the spectra for at least six months, which can characterize them as efficient stabilizing matrices of nanoparticles. 相似文献
17.
《Tetrahedron letters》2013,54(48):6427-6429
The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported. 相似文献
18.
19.
N. N. Il'chenko V. N. Britsun M. O. Lozinskii 《Theoretical and Experimental Chemistry》2005,41(5):284-289
The keto-enol-enethiol tautomerism in 3-oxo-3-R1-N-R2-propanethioamides under vacuum and in acetone was studied in terms of density functional theory. It was established that
the equilibrium depends on the structure of the 3-oxo-3-R1-N-R2-propanethioamides and on the nature of the solvent, but the most stable form is as a rule the keto form stabilized by an
intramolecular hydrogen bond.
__________
Translated from Teoreticheskaya i Eksperimental'naya Khimiya, Vol. 41, No. 5, pp. 272–277, September–October, 2005. 相似文献
20.
N. J. P. Subhashini Ch. Sravanthi K. Sravanthi Shivaraj 《Russian Journal of General Chemistry》2016,86(6):1405-1411
The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88% yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benzaldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, 1H NMR, 13C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial activity by the agar disc diffusion method. 相似文献