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Domino [3+1+1] heterocyclization providing an efficient umpolung strategy for synthesis of 2-(2′-azaaryl)imidazoles

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Abstract

Concise and efficient three-component domino [3+1+1] heterocyclization to highly substituted 2-(2′-azaaryl)imidazoles, promoted by K2CO3 under microwave irradiation conditions, has been developed. The reactions have broad substrate scope which includes a wide range of common commercially available aromatic aldehydes and heteroaryl-amidines. A mechanism involving the umpolung process has been proposed for formation of the 2-(2′-azaaryl)imidazoles.

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Acknowledgments

We are grateful for financial support from the National Science Foundation of China (21072163, 21232004, 21272095, and 21102124), PAPD of Jiangsu Higher Education Institutions, the NSF of Jiangsu Education Committee (11KJB150016), Jiangsu Science and Technology Support Program (no. BE2011045), the Qing Lan Project (12QLG006), and the Doctoral Research Foundation of Xuzhou Normal University (XZNU, no. 10XLR20).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 211116, People’s Republic of China

    Wei Fan, Li-Ping Fu, Bo Jiang & Shu-Jiang Tu

  2. Yunhe Teachers College, Xuzhou, Jiangsu, 221300, People’s Republic of China

    Xiao-Jing Zhang

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  1. Xiao-Jing Zhang
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  2. Wei Fan
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  3. Li-Ping Fu
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  4. Bo Jiang
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  5. Shu-Jiang Tu
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Correspondence to Bo Jiang or Shu-Jiang Tu.

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Zhang, XJ., Fan, W., Fu, LP. et al. Domino [3+1+1] heterocyclization providing an efficient umpolung strategy for synthesis of 2-(2′-azaaryl)imidazoles. Res Chem Intermed 41, 773–783 (2015). https://doi.org/10.1007/s11164-013-1227-8

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