Heterocyclic nitro compounds

Bagal, L. I.; Pevzner, M. S.; Frolov, A. N.; Sheludyakova, N. I.

doi:10.1007/bf00475005

Cited by 35 publications

(35 citation statements)

References 11 publications

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“…A similar regularity in the 1 H NMR spectra of triazoles 3b-5b permit us to identify triazole 5b as the 4-isomer. The agreement of the physical constants, in particular, the melting points, of triazoles 5a,b with the values given in earlier work [2,5,6] and comparative analysis of the 1 H NMR, IR, and UV spectra of these compounds and their analogs, 3a,b, 4a,b [1, 4,8] also support these assignments.…”

supporting

confidence: 73%

“…sodium carbonate and then distilled water, dried, and distilled in vacuum (purity ≥99.9%, the amount of acid calculated relative to sulfuric acid was ≤0.1%). Triazoles 1 and 2 were recrystallized twice from water and then from methanol; mp 214°C for 1 (210°C [5]) and mp 197°C for 2 (194°C [5]). …”

Section: Methodsmentioning

confidence: 99%

“…Thus, the chemical shift of the proton at C (5) in 4-methyltriazole 5a at 8.82 ppm is downfield relative to the ring protons in 1-methyltriazole 3a at 8.75 ppm and in 2-methyltriazole 4a at 8.15 ppm [1], while the singlet for the N-CH 3 group protons in triazole 5a at 3.93 ppm is upfield relative to the signal of the analogous protons in 1-methyltriazole 3a at 4.03 ppm and in 2-methyltriazole 4a at 4.18 ppm [1]. A similar regularity in the 1 H NMR spectra of triazoles 3b-5b permit us to identify triazole 5b as the 4-isomer.…”

mentioning

confidence: 98%

“…On the basis of the signals of the protons at C (5) in the 1 H NMR spectra, triazole 5a was identified as the 4H-isomer. Thus, the chemical shift of the proton at C (5) in 4-methyltriazole 5a at 8.82 ppm is downfield relative to the ring protons in 1-methyltriazole 3a at 8.75 ppm and in 2-methyltriazole 4a at 8.15 ppm [1], while the singlet for the N-CH 3 group protons in triazole 5a at 3.93 ppm is upfield relative to the signal of the analogous protons in 1-methyltriazole 3a at 4.03 ppm and in 2-methyltriazole 4a at 4.18 ppm [1].…”

mentioning

confidence: 99%

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Reactions of 3-Nitro-1,2,4-Triazole Derivatives with Alkylating Agents. 2. Alkylation of a Neutral Heterocycle by Dimethyl Sulfate

Суханов

Сакович

Sukhanova

et al. 2005

Chem Heterocycl Compd

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supporting

confidence: 73%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 98%

mentioning

confidence: 99%

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Reactions of 3-Nitro-1,2,4-Triazole Derivatives with Alkylating Agents. 2. Alkylation of a Neutral Heterocycle by Dimethyl Sulfate

Суханов

Сакович

Sukhanova

et al. 2005

Chem Heterocycl Compd

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“…The nitrotriazoles 1, 6, and 7 were prepared by the methods described in [35][36][37] and purified by recrystallization or vacuum sublimation just before use.…”

Section: Methodsmentioning

confidence: 99%

Radical-anions in the vicarious C-amination reactions of N-substituted nitrotriazoles

Vakul’skaya

Titova

Ларина

et al. 2006

Chem Heterocycl Compd

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The constant attention of synthetic chemists to the vicarious nucleophilic substitution of hydrogen is reflected in a series of detailed reviews [1][2][3]. During the vicarious substitution of hydrogen an amino group is readily introduced into nitro aromatic and nitro heteroaromatic compounds [4,5], and this opens up broad synthetic possibilities (in particular the Sandmeyer reaction) and in itself explains the increased interest in the vicarious nucleophilic substitution of hydrogen. Interest has recently shifted to study of the mechanism of the process [6-9].Having put forward the idea of possible electron transfer during the vicarious nucleophilic substitution of hydrogen [9] and having confirmed this for the vicarious amination of nitrobenzene and a series of N-methylated nitroazoles [10-12], we assumed that the lower the reduction potential of the nitroazole the more readily the latter should undergo amination in the vicarious nucleophilic substitution of hydrogen. Our papers on the electrochemical reduction of azoles in an aprotic medium [13,14] show that their first reduction potentials decrease both with the accumulation of nitrogen atoms in the heterocycle and with the introduction of phenylene fragments. Apparently, overlap of the orbitals of the unshared electron pairs of adjacent pyridine nitrogen atoms or increase in the aromaticity of the system help to reduce the energy of the LUMO and facilitate the transfer of an electron to the molecule being reduced. _______ * Dedicated to Academician M. G. Voronkov on his 85th birthday. __________________________________________________________________________________________

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Nitro‐substituted Oxadiazoles: Important Building Blocks in the Synthesis of Energetic Compounds

Pagoria¹

2022

Nitrogen‐Rich Energetic Materials

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Heterocyclic nitro compounds

Cited by 35 publications

References 11 publications

Reactions of 3-Nitro-1,2,4-Triazole Derivatives with Alkylating Agents. 2. Alkylation of a Neutral Heterocycle by Dimethyl Sulfate

Reactions of 3-Nitro-1,2,4-Triazole Derivatives with Alkylating Agents. 2. Alkylation of a Neutral Heterocycle by Dimethyl Sulfate

Radical-anions in the vicarious C-amination reactions of N-substituted nitrotriazoles

Nitro‐substituted Oxadiazoles: Important Building Blocks in the Synthesis of Energetic Compounds

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