- Sensitive Energetics from the N-Amination of 4-Nitro-1,2,3-Triazole
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Energetic N-amino-C-nitro compounds 1-amino-4-nitro-1,2,3-triazole and 2-amino-4-nitro-1,2,3-triazole are characterized for the first time as energetic materials. These compounds were characterized chemically by nuclear magnetic resonance (NMR), Infrared
- Wozniak, Dominique R.,Salfer, Benjamin,Zeller, Matthias,Byrd, Edward F. C.,Piercey, Davin G.
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p. 806 - 811
(2020/05/25)
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- Regioselective ortho-Acylation of N-Aryl-1,2,3-triazoles with Alcohols in Water
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A palladium-catalyzed regioselective ortho-acylation of N-aryl-1,2,3-triazoles has been achieved under aqueous conditions without the assistance of surfactants or additives. The reaction takes place by using benzylic, heterocyclic, and aliphatic alcohols as the acylating reagents and tert-butyl hydroperoxide (TBHP) as the oxidant and provides an alternative route for the synthesis of triazole-substituted aryl, heteroaryl, and aliphatic ketones in moderate to excellent yields.
- Premi, Chanchal,Patel, Shyam Sunder,Jain, Nidhi
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p. 3788 - 3795
(2016/08/16)
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- Synthetic approaches to 3,3'-biindolyl and 3,3'-biindazolyl derivatives
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In this paper new syntheses of 3,3'-biindolyl and 3,3'-biindazolyl derivatives are described. Formation of 3,3'-biindolyl derivatives by oxidative coupling of N-acetylindole with TeCl4 gave a good yield, while attempt to use the same reaction conditions for synthesis of 3,3'-biindazolyl derivatives failed. However, conversion of 3-haloindazole derivatives to its trimethylstannane derivative, followed by palladium-catalyzed Stille cross-coupling reaction, resulted in formation of 3,3'-biindazolyl derivatives.
- Nakhai, Azadeh,Bergman, Jan
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p. 309 - 318
(2014/01/17)
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- Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives
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The reaction of phenylhydrazine with a sugar dialdehyde in water, as a key step for the synthesis of the 3-amino-3-deoxy-d-glucose moiety contained in kanamycin, has been revisited. Structural studies (IR and NMR as well as a simple theoretical model base
- Franconetti, Antonio,Borrachero, Pastora,Gómez-Guillén, Manuel,Cabrera-Escribano, Francisca
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p. 249 - 253
(2013/03/14)
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- Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles
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2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium-zinc combination was next selected to apply the deprotonation-iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.
- Chevallier, Floris,Blin, Thomas,Nagaradja, Elisabeth,Lassagne, Frédéric,Roisnel, Thierry,Halauko, Yury S.,Matulis, Vadim E.,Ivashkevich, Oleg A.,Mongin, Florence
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scheme or table
p. 4878 - 4885
(2012/07/28)
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- Reaction of unsaturated esters with the oxidative system aluminum tri-tert-butoxide-tert-butyl hydroperoxide
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Unsaturated esters containing double bonds in the acyl (methyl acrylate) or in the alcohol (vinyl and allyl acetates) fragments are cleaved under mild conditions (20°C) by the system aluminum tri-tert-butoxide-tert-butyl hydroperoxide to give tert-butyl esters of peroxycarboxylic acids and unsymmetrical aluminum alkoxides. The double bond in the acyl fragment is inert to this oxidation system. Vinyloxy- and allyloxy derivatives are oxidized to hydroxyethanal and (hydroxymethyl)oxirane, respectively. Carbon-hydrogen bonds are oxidized only in allyl acetate.
- Stepovik,Martynova,Dodonov
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p. 1225 - 1229
(2007/10/03)
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- Thiol oxidation by 1,2,3-oxadiazolinium ions, presumed carcinogens
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3-Alkyl-1,2,3-oxadiazolinium ions 1 have been proposed as reactive intermediates in the activation of (2-hydroxyethyl)nitrosamines. The reaction of 3-methyl-1,2,3-oxadiazolinium tosylate (1a), 2-ethyl-1-methoxy-2- phenyldiazenium tetrafluoroborate (3), and 3-phenyl-1,2,3- oxadiazolinium triflate (1b) with thiols was investigated to determine the behavior of these compounds toward typical 'cellular nucleophiles'. Each of these substances oxidizes benzenethiol to diphenyl disulfide. The reaction aqueous buffer at pH 7.4 is rapid. Reaction of 1b with benzenethiol gives, in addition to the disulfide, benzene, biphenyl, azobenzene, diphenylsulfide, aniline, and glycolaldehyde. Similar products are obtained from 3. Phenyldiazene is postulated as an intermediate in this process, and its generation from phenyldiazoformate in the presence of benzenethiol gives similar products. Diazenes are presumed to arise by proton abstraction from the CH adjacent to N. The kinetic reaction of 1a with N-acetylcysteine to give the corresponding disulfide show first order dependence on each reactant and base catalysis. The data from these model chemical experiments suggests that 1,2,3- oxadiazolinium ions could react with abundant thiols in cells to lead to either their detoxification or radical processes emanating from diazenes. The occurrence of thiol-oxadiazolinium ion redox transformations could modulate the alkylation chemistry of these substances as well.
- Loeppky,Srinivasan
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p. 817 - 820
(2007/10/03)
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- Reactions of Substituted Hydrazines with Glyoxal
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Substituted hydrazines have been reacted with glyoxal to yield bis(hydrazone) derivatives.Cyclized products were not observed.Thermal decomposition of the glyoxal adducts was investigated.
- Gallucci, Robert R.
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p. 217 - 219
(2007/10/02)
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