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Vitamin B1-catalyzed one-pot ultrasound-assisted synthesis of 1,2-disubstituted benzimidazole and its selective recognition of metal ions

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Abstract

An efficient one-pot synthesis of 1,2-disubstituted benzimidazoles was developed via cyclocondensation starting from o-phenylenediamine with substituted aromatic aldehydes using catalyst vitamin B1 under ultrasound-assisted, and was characterized by HR-MS, FT-IR, 1H and 13C NMR spectroscopy. N-Ts-substituted 1,2-disubstituted benzimidazoles were formed when 2 equivalents of p-toluenesulfonic acid were added to the reaction. The reaction conditions of the method are environmentally friendly, no metal is required, the operation is simple, the substrates are extensive, the yield is high, and the catalyst is non-toxic and reusable. The crystal structure of compound 1-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1H-benzoimidazole (3ab) in triclinic P21/n space group is presented. 4-(1-(2,3,4-Trihydroxybenzyl)-1H-benzoimidazol-2- yl)benzene-1,2,3-triol (3af) as a metal ion fluorescent probe, has excellent selectivity to Pb2+ and Ag+, and exhibits obvious discoloration.

Graphical abstract

An efficient one-pot synthesis of 1,2-disubstituted benzimidazoles was developed via cyclocondensation starting from o-phenylenediamine with substituted aromatic aldehydes using catalyst vitamin B1 under ultrasound-assisted, and were characterized by HR-MS, FT-IR, 1H and 13C NMR spectroscopy. N-Ts-substituted 1,2-disubstituted benzimidazoles were formed when 2 equivalents of p-toluenesulfonic acid was added to the reaction. The crystal structure of compound 1-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1H-benzoimidazole (3ab) in triclinic P21/n space group was presented.

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Acknowledgements

We are grateful to Mr. C. Y. Wang for NMR spectra, Mr. Z. L. Wei for mass spectra. Financial support from ‘the education department of Jilin province (NO. JJKH20220233KJ)’ is gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Chengde Street 45, Jilin City, 132022, People’s Republic of China

    Chang Liu, Wenbin Xu, Wenyu Li, Yulu Zhang & Dawei Zhang

  2. College of Aeronautical Engineering, Jilin Institute of Chemical Technology, Jilin City, 132022, People’s Republic of China

    Lu Ren

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  1. Chang Liu
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  4. Wenyu Li
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Contributions

CL done investigation; validation; and writing-original draft preparation. WBX and YLZ done the synthesis and characterization of compounds. LR and WYL done metal ion detection. DWZ did project administration, supervised the work, revised, and completed the manuscript.

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Correspondence to Dawei Zhang.

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Liu, C., Ren, L., Xu, W. et al. Vitamin B1-catalyzed one-pot ultrasound-assisted synthesis of 1,2-disubstituted benzimidazole and its selective recognition of metal ions. Res Chem Intermed 49, 2529–2548 (2023). https://doi.org/10.1007/s11164-023-05011-9

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