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One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles

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Abstract

An efficient strategy for the synthesis of pyrrolo[1,2-\(a\)]-benzimidazole (PBI) linked to an ionic liquid (ILs) as a soluble support under microwave irradiation was explored. The key intermediate benzimidazoles were synthesized via N-acylation followed by cyclodehydration of IL-supported methyl-3-amino-4-(isobutylamino) benzoate. The synthesis of the IL-bound PBI was performed by one-pot three-component condensation under microwave dielectric heating, which involved a Knoevenagel condensation and a [4+1]-cycloaddition reaction. The reaction was monitored directly by means of \(^{1}\)H NMR. All final products were obtained in good yield and high purity after precipitation.

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Acknowledgments

The authors wish to thank the National Science Council (NSC) of Taiwan for financial support and the authorities of the National Chiao Tung University for providing the laboratory facilities. This study was particularly supported by the “Centre for bioinformatics research of aiming for the Top University Plan” of the National Chiao Tung University and Ministry of Education, Taiwan.

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  1. Department of Applied Chemistry, National Chiao Tung University, Hsinchu, 300, Taiwan, ROC

    Wei-Shun Hsu, Vijaykumar Paike & Chung-Ming Sun

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  1. Wei-Shun Hsu
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Correspondence to Chung-Ming Sun.

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Hsu, WS., Paike, V. & Sun, CM. One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles. Mol Divers 17, 285–294 (2013). https://doi.org/10.1007/s11030-013-9433-2

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