Thermal transformations of 2H-benzimidazole 1,3-dioxides

Samsonov, V. A.; Bagryanskaya, I. Yu.; Gatilov, Yu. V.; Savel'ev, V. A.

doi:10.1007/s11172-011-0257-x

Cited by 7 publications

(4 citation statements)

References 18 publications

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“…It should be noted that the nitrosation reaction of phloroglucinol led to 2,4,6‐trihydroxyimino‐cyclohexane‐1,3,5‐trione in the forms of sodium salts [19] . In our case, with an intensive nitrosation reaction proceeding about 1–2 hours, NaH 2 L 1 was precipitated, but if keep stirring vigorously more than 3 hours, a homogeneous red solution is formed and cannot separated the precipitation.…”

Section: Resultsmentioning

confidence: 53%

Novel Products of Nitrosation of a Series of Trihydroxybenzene Derivatives and Their Complexation with Cu(II), Cd(II) and Fe(III): Synthesis, Characterization, and Theoretical Modeling

et al. 2021

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Three novel bis-and trinitroso compounds derived from 1,3,5trihydrohybenzene (phloroglucinol), 2,4,6-trihydroxy benzoic acid, and 2,4,6-trihydroxyacetophenone were isolated, their spectral characteristics, ionization constants and thermodynamic parameters of dissociation process were calculated. The comparison of the stability of nitroso and hydroxylimino tautomeric forms was performed by DFT calculations. Nine complexes of the ligands with Cu(II), Cd(II), and Fe(III), were isolated and studied by elemental analyses, X Ray analysis and spectroscopic methods. According to the crystal structure determination, the Cd complex with the phloroglucinol based ligand exists in the form of a binuclear compound. The QTAIM Bader topological analysis indicated that the binuclearity of the Cd complex is due to strong interatomic interactions between Cd atoms with bifurcate carbonyl groups of the ligands and strong H-interactions involving coordinated and lattice water molecules. The equilibria of reactions of complex formation of the organic species with Cu 2 + , Cd 2 + , and Fe 3 + was studied by spectrophotometric titration, and the composition of the complexes in solutions and their stability constants were calculated. The ability of the isolated organics to remove metal cations from the aqueous solutions was studied in the pH interval 3-6 and the rate of Cu 2 + removal from aqueous solutions was found close to 100 %.

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Section: Resultsmentioning

confidence: 53%

Novel Products of Nitrosation of a Series of Trihydroxybenzene Derivatives and Their Complexation with Cu(II), Cd(II) and Fe(III): Synthesis, Characterization, and Theoretical Modeling

et al. 2021

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“…Presumably, initial elimination of N-oxide oxygen atoms from molecule I gives the corresponding 2H-benzimidazole which then reacts with aromatic amine. As shown by us previously [10], compound I is a strong oxidant, and it loses N-oxide oxygen atoms on heating. This is likely to be responsible for the formation of a considerable amount of tars in the reaction of I with aromatic amines.…”

Section: -Nitrospiro[benzimidazole-21′mentioning

confidence: 53%

“…The elemental compositions were determined at the Microanalysis Laboratory, Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences. Compounds I [7] and VI [10] were synthesized by known methods.…”

Section: Methodsmentioning

confidence: 99%

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Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with nucleophiles

et al. 2012

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Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with aliphatic amines and sodium hydroxide resulted in removal of one N-oxide oxygen atom and formation of 4-alkylamino-or 4-hydroxy-substituted 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1-oxides, respectively. The title compound reacted with ammonia and methylamine in the presence of MnO 2 with conservation of both N-oxide moieties, and the products were 4-amino-and 4-methylamino-5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxides. The reactions with aromatic amines were accompanied by removal of both N-oxide oxygen atoms with formation of N-

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2H-Benzimidazole N-oxides: synthesis, chemical properties, and biological activity

et al. 2018

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Thermal transformations of 2H-benzimidazole 1,3-dioxides

Cited by 7 publications

References 18 publications

Novel Products of Nitrosation of a Series of Trihydroxybenzene Derivatives and Their Complexation with Cu(II), Cd(II) and Fe(III): Synthesis, Characterization, and Theoretical Modeling

Novel Products of Nitrosation of a Series of Trihydroxybenzene Derivatives and Their Complexation with Cu(II), Cd(II) and Fe(III): Synthesis, Characterization, and Theoretical Modeling

Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with nucleophiles

2H-Benzimidazole N-oxides: synthesis, chemical properties, and biological activity

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