A. A. Voronin
Russian Academy of Sciences
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Russian Chemical Bulletin | 2015
A. A. Voronin; V. P. Zelenov; A. M. Churakov; Yu. A. Strelenko; V. A. Tartakovsky
Abstract1H-[1,2,3]Triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide (3) was synthesized by reduction of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide (1) with PCl3, reduction of 1-methoxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide (4) with Na2S2O4, and by the reaction of compound 4 with Et3N. Both methylation of compound 3 with diazomethane and reaction of Ag-salt of compound 3 with MeI occur at the triazole cycle to give all three possible isomers. The structures of the synthesized compounds were confirmed by 1H, 13C, 14N, and 15N NMR spectroscopy.
Russian Chemical Bulletin | 2013
V. P. Zelenov; A. A. Voronin; A. M. Churakov; Yu. A. Strelenko; Marina I. Struchkova; V. A. Tartakovsky
Abstract3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ⇒ 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-[(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 7 → 8 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time.
Russian Chemical Bulletin | 2014
V. P. Zelenov; A. A. Voronin; A. M. Churakov; Yu. A. Strelenko; V. A. Tartakovsky
A new approach to the synthesis of 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazole 1-oxides 1 was developed. Compounds 1 were obtained by reactions of 3-amino-4-(tert-butyl-NNO-azoxy)furoxan with aliphatic amines RNH2 (R = Me, Et, Pri, Bu, and But). 4-Amino-5-(tert-butyl-NNO-azoxy)-2-tert-butyl-2H-1,2,3-triazole 1-oxide was transformed under the action of acids into 4-amino-5-(tert-butyl-NNO-azoxy)-1-hydroxy-1H-1,2,3-triazole. Methylation of the latter with diazomethane mainly involves the O atom of the triazole oxide ring. Reduction of compounds 1 gave 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazoles and 4-amino-5-(tert-butyldiazenyl)-2-R-2H-1,2,3-triazoles (R = Me, Pri, and But). The structures of the compounds obtained were confirmed by 1H, 13C, and 14N NMR spectroscopy.
Russian Chemical Bulletin | 2014
A. A. Voronin; V. P. Zelenov; A. M. Churakov; Yu. A. Strelenko; V. A. Tartakovsky
Alkylation of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide 1 and its silver salt 10 with different alkylating agents (diazomethane, diazoacetone, bromoacetone, α-bromoacetophenone, methyl iodide, methyl vinyl ketone) was studied. Alkylation of compound 1 with diazo compounds and salt 10 with halocompounds results predominantly in O-alkylation products, 1-alkoxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxides. The Michael reaction of compound 1 with methyl vinyl ketone involves the triazole nitrogen atom to give 1-(3-oxobutyl)-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 3,4,6-trioxide. The structures of the compounds synthesized were established by 1H, 13C, 14N NMR spectroscopy and mass spectrometry.
Russian Chemical Bulletin | 2012
V. P. Zelenov; A. A. Voronin; A. M. Churakov; M. S. Klenov; Yu. A. Strelenko; V. A. Tartakovsky
Abstract3-(N-Nitroamino)-4-phenylfuroxan, the first representative of the furoxan series that contains the N-nitroamino group in position 3 of the furoxan ring, was obtained. This compound is not very stable; its structure was confirmed by chemical transformations into an ammonium salt and N- and O-methyl derivatives. Under standard conditions for oxodiazonium ion generation from nitramine, 3-(N-nitroamino)-4-phenylfuroxan underwent a transformation into the corresponding azofuroxan, viz., 3,3′-diazenediylbis(4-phenyl-1,2,5-oxadiazole 2-oxide), while the O-methyl derivative of 3-(N-nitroamino)-4-phenylfuroxan yielded 2-hydroxyimino-2-phenylacetonitrile. The changed reactivity of the oxodiazonium ion was explained by its intramolecular interaction with the exocyclic O atom of the furoxan system.
Russian Chemical Bulletin | 2017
A. M. Churakov; S. L. Ioffe; A. A. Voronin; V. A. Tartakovsky
Nitration of N,N′-bis(trimethylsilyl)carbodiimide with N2O5 or (NO2)2SiF6 afforded N-nitro-N´-(trimethylsilyl)carbodiimide, the first representative of N-nitro carbodiimides. Its further nitration led to the release of CO2, which is presumably formed in the course of N,N´-dinitrocarbodiimide decomposition. The reactions of N-nitro-N´-(trimethylsilyl)carbodiimide with nucleophiles take place both at the tri methylsilyl group (for example, with NH3) to give nitrocyanamide salts and at the carbodiimide C atom (for example, with Et2NH) to give the corresponding nitroguan idines.
Russian Chemical Bulletin | 2015
A. A. Voronin; A. M. Churakov; Ivan V. Fedyanin; V. P. Zelenov; V. A. Tartakovsky
A new intramolecular reaction involving neighboring (tert-butyl-NNO-azoxy) and N-nitroamine groups was found, which gave the first representatives of 5-diazo-1,2,3-triazol-4-ones: 3-acetoxy- and 3-hydroxy-5-diazo-3,5-dihydro-4H-1,2,3-triazol-4-ones. The structure of the products was confirmed by X-ray diffraction and NMR spectroscopy data.
Russian Chemical Bulletin | 2018
A. M. Churakov; S. L. Ioffe; A. A. Voronin; V. A. Tartakovsky
Reaction of N-Alk-N′-(trimethylsilyl)carbodiimides (Alk = Me, But) with nitrating agents (N2O5, (NO2)2SiF6) affords alkyl(nitro)cyanamides and N-alkyl-N′-nitrocarbodiimides. The product ratio depends on the reaction conditions. N-(tert-butyl)-N′-nitrocarbodiimide can be obtained in almost pure form. This compound is stable at temperatures below 10 °C. Its structure was confirmed by 1Н, 13C, and 14N NMR. The reaction of N-(tert-butyl)-N′-nitrocarbodiimide with amines provides a new route to N-alkyl(aryl)-substituted N′-(tert-butyl)-N″-nitroguanidines.
Tetrahedron | 2014
A. A. Voronin; V. P. Zelenov; A. M. Churakov; Yurii A. Strelenko; Ivan V. Fedyanin; V. A. Tartakovsky
Russian Chemical Bulletin | 2011
V. P. Zelenov; A. A. Voronin; A. M. Churakov; M. S. Klenov; Yu. A. Strelenko; V. A. Tartakovsky