Structural analysis of 1-vinylbenzazoles by 1H and 13C NMR spectroscopy

1-Vinylbenzotriazole undergoes lithiation at the a-carbon and subsequent reactions with electrophiles to afford 1-(1-substituted viny1)benzotriazoles (3a -d). Similarly, 1-( 1-substituted propeny1)-(9a-c. 9e, 10a-c, 10e) and 2-(1-methylpropenyl)-benzotriazoles (14 and 15) were prepared by lithiation of the corresponding 1-and 2-propenyl-benzotriazoles followed by alkylation. 1-and 2-Allylbenzotriazoles 4 and 5 are also lithiated at the a-carbon and the intermediates react with electrophiles at this position. The structures of the propenyl derivatives were supported by an alternative synthetic route via rearrangements of the corresponding allyl isomers. 1-Propargylbenzotriazole (16) undergoes lithiation first at the acetylenic CH and then at the CH2 group. The dilithiated species, produced by treatment of 16 with two equivalents of butyllithium, reacts with an electrophile first at the carbon atom adjacent to the nitrogen atom, and then at the terminal carbon atom. Hence lithiation of 16 and subsequent reactions with electrophiles afford alkylated products l?a -d, 18a -d, 19a -b and 20a -c depending upon the amount of butyllithium and of the electrophile(s) used. The structures of each class of product were supported by spectral and analytical data.

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N‐Vinyl‐, N‐Allyl‐, N‐Propenyl‐ and N‐Propargyl‐benzotriazoles: Reactions of Their Lithium Derivatives

Katritzky

Malhotra

1992

Liebigs Ann. Chem.

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Metal Complexes of Cobalt Chloride with Vinyl‐, Allyl‐ and Styrylbenzimidazole Ligands: Synthesis, Structure, and Properties

Sterkhova,

Parshina,

Grishchenko

et al. 2024

ChemistrySelect

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Three N‐substituted benzimidazole cobalt(II) complexes have been synthesized and fully characterized by elemental analysis, FT‐IR spectroscopy, and X‐ray crystallography. The crystal packing formation features were studied by AIM analysis, and the energy and nature of both weak noncovalent interactions in the crystal and metal–ligand coordination bonds were assessed. These N‐coordinated cobalt(II) complexes were screened for antimicrobial activities against Gram‐negative (Escherichia coli, Bacillus subtilis) and Gram‐positive (Enterococcus durans) bacteria. Minimal inhibitory concentrations (MIC = 6.2 mg/mL) were found for complex cobalt chloride with allylbenzimidazole ligands against E. durans and E. coli. Its antimicrobial activity is several times higher compared to the reference gentamicin. Molecular docking made it possible to consider the nature of binding of cobalt metal complexes with vinyl‐, allyl‐ and styrylbenzimidazole ligands to biological targets and estimate their energy. The binding energy meanings depend on protein and ligand type, and reaches 8 kcal/mol.

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Structural analysis of 1-vinylbenzazoles by 1H and 13C NMR spectroscopy

Cited by 2 publications

References 3 publications

N‐Vinyl‐, N‐Allyl‐, N‐Propenyl‐ and N‐Propargyl‐benzotriazoles: Reactions of Their Lithium Derivatives

N‐Vinyl‐, N‐Allyl‐, N‐Propenyl‐ and N‐Propargyl‐benzotriazoles: Reactions of Their Lithium Derivatives

Metal Complexes of Cobalt Chloride with Vinyl‐, Allyl‐ and Styrylbenzimidazole Ligands: Synthesis, Structure, and Properties

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