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\(\hbox {I}_{2}\)-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine

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Abstract

Under solvent-free high-speed ball milling, an I\(_{2}\)-promoted condensation/cyclization of easily available methyl ketones or 1,3-dicarbonyl compounds with 2-aminopyridines has been developed, which allows the quick assembly of 2,3-substituted imidazo[1,2-a]pyridines (IPs) with broad molecular diversity, including the antiulcer drug zolimidine. The advantages of high yields, good functional group compatibility, short reaction time (within 90 min), free use of heating, solvent and metal, employment of cheap starting materials, and simple work-up procedure make this protocol a very efficient alternative to traditional synthesis of IPs.

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Acknowledgments

We are grateful to financial support from the National Natural Science Foundation of China (21242013) and Key Projects for Outstanding Young Talents in Colleges and Universities of Anhui Province (No. gxyqZD2016121).

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Authors and Affiliations

  1. School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu, 241000, Anhui, People’s Republic of China

    Fang-Jian Wang, Hui Xu & Ze Zhang

  2. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Ming Xin

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  1. Fang-Jian Wang
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  2. Hui Xu
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Correspondence to Ze Zhang.

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Wang, FJ., Xu, H., Xin, M. et al. \(\hbox {I}_{2}\)-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine. Mol Divers 20, 659–666 (2016). https://doi.org/10.1007/s11030-016-9666-y

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