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1.
G. T. Sukhanov A. G. Sukhanova Yu. V. Ilyasova 《Chemistry of Heterocyclic Compounds》2006,42(9):1197-1199
The reaction of 3-nitro-5-R-1,2,4-triazoles with diethyl sulfate gives 1-ethyl-3-R-5-nitro-, 4-ethyl-3-nitro-5-R-1,2,4-triazoles,
1,4-diethyl-, 1,4-diethyl-3-methyl-1,2,4-triazol-5-ones, and 1,4-diethyl-3-nitro-5-R-1,2,4-triazolium salts. When compared
with the use of dimethyl sulfate as alkylating agent the ethylation products have a markedly increased fraction of triazolones
(up to 30–37%) and a somewhat lowered yield of nitrotriazolium salts (up to 6–10%). The reaction time is increased by an order.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1378–1381, September, 2006. 相似文献
2.
Sergei V. Voitekhovich Pavel N. Gaponik Juliya V. Filipova Gennady T. Sukhanov 《Tetrahedron letters》2009,50(21):2577-971
The products of the alkylation of sodium 4-nitro-1,2,3-triazolate with ethyl bromide were investigated using 1H, 13C, and 15N NMR spectroscopy. It was found that alkylation proceeds on the triazole nitrogen atoms giving a mixture of three isomeric N-ethyl-4-nitro-1,2,3-triazoles. The molar ratio of N1, N2, and N3-alkylation products was 4:8:1. The formation of a minor N3-isomer, namely 1-ethyl-5-nitro-1,2,3-triazole was confirmed by X-ray structural analysis of single crystals of its tetranuclear copper(II) complex obtained by reaction of copper(II) chloride dihydrate with a mixture of the N2 and N3-isomers. 相似文献
3.
《Mendeleev Communications》2022,32(2):215-217
New selective synthesis of 1-alkyl-5-nitro-1,2,3-triazoles and 1-alkyl-4-nitro-1,2,3-triazoles has been developed, involving acid N-dealkylation of the relative 4-nitro-1,2,3- and 3-nitro- 5-R-1,2,4-triazolium salts. The assortment of novel 1-alkyl- 4(5)-nitro-1,2,3-triazoles has been thus essentially expanded. Treatment of relative 3-nitro-1,2,4-triazolium salts with HCl or HBr proceeds mostly as SNipso-substitution of the nitro group. 相似文献
4.
Yu. A. Strelenko T. I. Godovikova E. L. Ignat'eva 《Chemistry of Heterocyclic Compounds》2002,38(5):547-552
Analysis of the 14N and 15N NMR spectroscopic data of 2-methyl-4,5-dinitro-1,2,3-triazole and of substituted 2-methyl-4(5)-nitro-1,2,3-triazole 1-oxides has shown the possibility of applying them for confirmation of the structures of the studied compounds. 相似文献
5.
O. A. Ivashkevich Vadim E. Matulis P. N. Gaponik G. T. Sukhanov J. V. Filippova A. G. Sukhanova 《Chemistry of Heterocyclic Compounds》2008,44(12):1472-1482
Quantum-chemical calculations have been carried out on molecular electrostatic potentials, proton affinity in the gas phase,
gas phase basicity, and pK
BH+ values in aqueous solution for C-nitro- and N-alkyl-4(5)-nitro-1,2,3-triazoles, and the relative stability of the isomeric
N-alkyl-4(5)-nitrotriazoles (alkyl = Me, Et, i-Pr, t-Bu) in the gas phase and in aqueous solution. For all the studied substances in the gas phase the 2H-tautomer and the N(2)-isomers
were considerably more stable than the corresponding N(1) compounds, and the 3H-tautomer and N(3)-isomer were the least stable.
In aqueous solution 1- and 3-isomers had close values of energies, but in the case of C-nitro-1,2,3-triazole the 1H form became
even more stable than the 2H-form. It was established which ring nitrogen atoms of 1,2,3-triazoles are protonated in the gas
phase and in solution. The obtained data correlate well with the results of experimental investigations on the alkylation
of 1,2,3-triazoles in acidic and basic media and of the experimental investigation on the alkylation of C-nitro-1,2,3-triazoles
with diethyl sulfate carried out in the present work.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1816–1828, December, 2008. 相似文献
6.
V. Yu. Korotaev V. Ya. Sosnovskikh I. B. Kutyashev M. I. Kodess 《Russian Chemical Bulletin》2006,55(11):2020-2031
The nucleophilic addition of acetylacetone and ethyl acetoacetate at the double bond of 3-nitro-2-trihalomethyl-2H-chromenes in the presence of NaH affords 2,3,4-trisubstituted chromanes containing the β-dicarbonyl fragment at position
4. The trans-trans configuration and the enol structure of the reaction products were confirmed by 1H NMR spectroscopy and X-ray diffraction. Treatment of these compounds with hydrazine gives the corresponding 3-nitro-4-(pyrazol-4-yl)-2-trihalomethylchromanes.
The reactions of 3-nitro-2-trihalomethyl-2H-chromenes with nitromethane and nitroethane in the presence of K2CO3 produce 1,3-dinitro derivatives of the chromane series.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1945–1955, November, 2006. 相似文献
7.
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
8.
Based on the full-optimized molecular geometric structures at B3LYP/6-31G* and B3P86/6-31G* levels, the densities (ρ), detonation
velocities (D), and pressures (P) for a series of 1,2,3-triazole derivatives, as well as their thermal stabilities, were investigated to look for high energy
density compounds (HEDCs). The heats of formation (HOFs) are also calculated via designed isodesmic reactions. The calculations
on the bond dissociation energies (BDEs) indicate that the BDEs of the initial scission step are between 53 and 70 kcal/mol,
and 4-nitro-1,2,3-triazole is the most reactive compound, while 1-(2′,4′-dinitrophenyl)-5-nitro-1,2,3-triazole is the least
reactive compound for 1,2,3-triazole derivatives studied. The condensed phase heats of formation are also calculated for the
title compounds. These results would provide basic information for the further studies of HEDCs. The detonation data of 1-(3′,4′-dinitrophenyl)-4-nitro-1,2,3-triazole
and 1-(2′,4′-dinitrophenyl)-4-nitro-1,2,3-triazole show that they meet the requirement for HEDCs. 相似文献
9.
G. T. Sukhanov A. G. Sukhanova Yu. V. Sheikov 《Chemistry of Heterocyclic Compounds》2007,43(6):786-792
Interaction of N(1)-alkyl-substituted 3-nitro-5-R-1,2,4-triazoles with dialkyl sulphates proceeds selectively and results in the respective salts
of 1,4-dialkyl-, 1,4,5-trialkyl-3-nitro-1,2,4-triazoliums. The reaction of N(4)-alkyl-substituted 3-nitro-5-R-1,2,4-triazoles yields the mixtures of the salts of 1,4-dialkyl-, 1,4,5-trialkyl-3-nitro-1,2,4-triazoliums
and 1,4-dialkyl-, 1,3,4-trialkyl-1,2,4-triazol-5-ones with predominance of quaternary salts.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 927–934, June, 2007. 相似文献
10.
G. V. Sakovich G. T. Sukhanov Yu. V. Filippova A. G. Sukhanova K. K. Bosov 《Russian Chemical Bulletin》2013,62(1):111-116
Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in concentrated H2SO4 occurs at all three endocyclic N atoms, giving a mixture of isomeric N(1)-, N(2)-, and N(3)-alkyl-4-nitro-1,2,3-triazoles (alkyl is isopropyl, sec-butyl, and cyclohexyl). The selectivity of the alkylation depends on the alcohol used. The most selective alkylation is provided at the N(2) atom when isopropyl (81%) and sec-butyl alcohols are used (67%). With an increase in the reaction time, also in the order isopropyl-, sec-butyl-, and cyclohexyl-4-nitro-1,2,3-triazoles, the N(2)-isomers undergo isomerization into N(1)-alkyl-4-nitro-1,2,3-triazoles. In all the cases, the fraction of the N(3)-substitution products in the mixtures is 6–30%. 相似文献
11.
A. T. Baryshnikov V. I. Erashko N. I. Zubanova B. I. Ugrak S. A. Shevelev A. A. Fainzil'berg A. L. Laikhter L. G. Mel'nikova V. V. Semenov 《Russian Chemical Bulletin》1992,41(4):751-757
Several chemoselective syntheses have been developed for 4-nitro-1,2,3-triazoles from sodium azide and gem-dinitroethylenes prepared from readily available transformation products of dinitroacetic acid ester: N-(,-dinitroethyl)-N,N-dialkylamines, 2,2-dinitroethanol acetate, a mixture of dinitroacetic acid ester with aliphatic aldehydes, or 1,1,1-trinitroalkanes. Hitherto-unknown 4-nitro-5-amino- and 4,5-dinitro-1,2,3-triazoles have been synthesized via successive transformations of the CH3 groups in 5-nitro-4-methyltriazole. Nitration of 4-nitro-1,2,3-triazole with nitronium fluoroborate or acetyl nitrate gave an unknown 2,4-dinitro-1,2,3-triazole.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 4, pp. 958–966, April, 1992. 相似文献
12.
The complex formation of 1,2,3-selenadiazoles with boron trifluoride etherate and phenyldichloroborane has been studied. The
molecular structure of the5-ethoxycarbonyl-4-methyl-1,2,3-selenadiazole has been confirmed by X-ray analysis.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 289–293, February, 2007. 相似文献
13.
T. I. Vakul’skaya I. A. Titova L. I. Larina O. N. Verkhozina G. V. Dolgushin V. A. Lopyrev 《Chemistry of Heterocyclic Compounds》2006,42(11):1427-1434
The vicarious nucleophilic substitution of hydrogen in symmetrical and vicinal nitrotriazoles by 1,1,1-trimethylhydrazinium
iodide in t-BuOK/DMSO was studied by ESR. In the ESR monitoring of the reactions the primary radical-anions of 4-nitro-2-phenyl-1,2,3-triazole
and 1-methyl-3-nitro-1,2,4-triazole were detected and characterized. It was shown by NMR that the amination of 4-nitro-2-phenyl-1,2,3-triazole
takes place exclusively in the triazole ring with the formation of 5-amino-4-nitro-2-phenyl-1,2,3-triazole. 1-Methyl-3-nitro-1,2,4-triazole,
like 3-nitro-1,2,4-triazole, does not form amination products. A possible mechanism for the vicarious C-amination of nitrotriazoles
and the formation of the radical-anions of the substrates is discussed.
Dedicated to Academician M. G. Voronkov on his 85th birthday.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1662–1670, November, 2006. 相似文献
14.
A. V. Serebryannikova L. V. Lapshina I. E. Efremova V. V. Gurzhiy A. E. Ryabinin 《Russian Journal of General Chemistry》2018,88(8):1612-1617
2-Benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and its analogs have been introduced in the aza-Michael reaction with hydrazine derivatives. Novel polysubstituted nitrosulfolenes have been obtained; their structures have been confirmed using 1Н NMR and IR spectroscopy as well as X-ray diffraction analysis. 相似文献
15.
V. M. Berestovitskaya N. A. Anisimova O. N. Kataeva N. G. Makarova G. A. Berkova 《Russian Journal of General Chemistry》2007,77(9):1567-1575
1,3-Dipolar cycloaddition of alkyl 3-nitro-and 3-bromo-3-nitroacrylates to phenyl azide gives regioisomeric alkyl 5(4)-nitro-1-phenyl-4,5-dihydro-1H-1,2,3-triazole-4(5)-carboxylates, the corresponding triazoles both with and without nitro group, and alkyl 3-nitro-1-phenylaziridine-2-carboxylates. Nitrotriazolecarboxylates were found to lose the ester moiety during chromatographic separation of the products on aluminum oxide. The structure of the products was determined on the basis of IR, 1H NMR, and X-ray diffraction data. 相似文献
16.
T. M. Khomenko D. V. Korchagina K. P. Volcho N. F. Salakhutdinov 《Russian Journal of Organic Chemistry》2009,45(9):1402-1404
Both enantiomers of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole 1-oxide as analogs of Varacins B and C were synthesized
for the first time. The use of the Modena method ensures higher optical purity but lower yields of the chiral sulfoxides,
as compared to the Kagan procedure. 相似文献
17.
L. I. Vereschagin F. A. Pokatilov V. N. Kizhnyaev 《Chemistry of Heterocyclic Compounds》2008,44(1):1-19
Published data on methods for the synthesis of substituted 4(5)-nitro-1,2,3-triazoles and their properties are reviewed.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–25, January, 2008. 相似文献
18.
A. G. Sukhanova G. V. Sakovich G. T. Sukhanov 《Chemistry of Heterocyclic Compounds》2008,44(11):1368-1373
Reaction of 3-nitro-1,2,4-triazole and 5-methyl-3-nitro-1,2,4-triazole with secondary and tertiary alcohols in conc. H2SO4 takes place at the N(2) atom. Alkylation by 2-propanol occurs regioselectively to form the 1-isopropyl-3-nitro-and 1-isopropyl-3-methyl-5-nitro-1,2,4-triazoles.
As a consequence of isomerization the alkylation using cyclohexyl or tert-butyl alcohols gives respectively a mixture of regioisomers
substituted at atom N(1) (1-cyclohexyl-3-nitro-and 1-cyclohexyl-5-methyl-3-nitro-1,2,4-triazoles) and at atom N(2) (5-nitro-1-cyclohexyl-and
1-cyclohexyl-3-methyl-5-nitro-1,2,4-triazoles) and, in the second case, to 1-tert-butyl-3-nitro-1,2,4-triazole.
* For Communication 5 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1680–1687, November, 2008. 相似文献
19.
C. G. Overberger Y. Kawakami 《Journal of polymer science. Part A, Polymer chemistry》1978,16(6):1249-1263
Water-soluble copolymers containing imidazole and N-alkylated imidazole pendant groups have been synthesized in order to investigate the hydrophobic interactions between polymeric catalysts and long alkyl chain ester substrates. Copoly[1-methyl-4-vinyl-imidazole/4(5)-vinylimidazole],copoly[1-methyl-5-vinylimidazole/4(5)-vinylimidazole], copoly[1-ethyl-5-vinylimidazole/4-(5)-vinyl-imidazole] and copoly[1-propyl-5-vinylimidazole/4(5)-vinylimidazole] were synthesized and their catalytic activity toward 3-nitro-4-acyloxybenzoic acid substrates (Sn?) was determined in 28.5% ethanol–water and in water and compared with that of the mixtures of homopolymers. Hydrophobic interactions were important for rate enhancement of the hydrolysis of long-chain ester substrates compared to that of short-chain ester substrates. The copolymers catalyzed the hydrolysis of 3-nitro-4-dodecanoyloxy-benzoic acid (S12?) about two times faster than the mixtures at pH 7.11 in 28.5% ethanol–water. The hydrolysis of S12? by the copolymers was about five times faster in water than 28.5% ethanol–water. 相似文献
20.
A. I. Gurkovskii N. N. Tonkikh M. V. Petrova A. Ya. Strakov 《Chemistry of Heterocyclic Compounds》1999,35(5):625-629
Reaction of 5,5-dimethyl-2-formylcyclohexane-1,3-dione with 4-methyl-, 4-benzoyl-, and 4-nitro-1,2-diaminobenzenes gave the
corresponding 2-(2-amino-4-methylphenylaminomethylene)-, 2-(2-amino-5-benzoylphenylaminomethylene)-, and 2-(2-amino-5-nitrophenylaminomethylene)-5,5-dimethylcyclohexane-1,3-diones.
When treated with hydrochloric acid, they cyclize to 7-methyl-, 8-benzoyl-, and 8-nitro-3,3-dimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinon
hydrochlorides. Under hydrolytic conditions the salts of 3,3,7-trimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinone
and 3,3-dimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinone undergo the C11−N10 bond cleavage to give N-(2-aminophenyl)- and N-(2-amino-5-methylphenyl)-substituted 3-amino-2-formyl-5,5-dimethylcyclohex-2-enones.
Ring opening of the hydrochlorides of 8-benzoyl-, and 3,3-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinones
occurs at the C−N5 bond and gives the starting enamines.
Riga Technical University, Riga LV-1658, Latvia; Translated from Khimiya Geterotsiklicheskikh Soedinenii, N. 5, pp. 696–700,
May, 1999. 相似文献