A novel domino strategy for forming poly-substituted quaternary imidazoles through a Cs2CO3-promoted aryl migration process

Hai-Wei Xu; Wei Fan; Meng-Yuan Li; Bo Jiang; Shu-Liang Wang; Shu-Jiang Tu

doi:10.1039/C3OB40666K

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A novel domino strategy for forming poly-substituted quaternary imidazoles through a Cs₂CO₃-promoted aryl migration process†

Hai-Wei Xu,^a Wei Fan,^a Meng-Yuan Li,^a Bo Jiang,*^a Shu-Liang Wang^a and Shu-Jiang Tu*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, P. R. China
E-mail: jiangchem@jsnu.edu.cn, laotu@jsnu.edu.cn
Fax: +0086-516-83500065
Tel: +0086-516-83500065

Abstract

A new domino strategy for the synthesis of highly functionalized quaternary imidazole derivatives via [3 + 2] heterocyclization, involving aryl migration and ring-opening of oxirane, has been developed. This domino reaction enables the successful assembly of three new sigma bonds including two C–N bonds in a simple operation. Features of this strategy include the mild conditions, convenient operation, and short reaction periods (15–20 min).

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Article information

DOI: https://doi.org/10.1039/C3OB40666K
Article type: Communication
Submitted: 04 Apr 2013
Accepted: 16 Apr 2013
First published: 16 Apr 2013

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Org. Biomol. Chem., 2013,11, 3603-3607

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A novel domino strategy for forming poly-substituted quaternary imidazoles through a Cs₂CO₃-promoted aryl migration process

H. Xu, W. Fan, M. Li, B. Jiang, S. Wang and S. Tu, Org. Biomol. Chem., 2013, 11, 3603 DOI: 10.1039/C3OB40666K

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Organic & Biomolecular Chemistry