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Copper/l-proline-catalyzed synthesis of 5-amino-2,3-diphenylimidazo[2,1-a]isoquinolines in the presence of Cs2CO3

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Abstract

Malononitrile underwent α-arylation with 2-(2-bromophenyl)-4,5-diphenyl-1H-imidazole to give a subsequent nucleophilic addition and dehydration products of 5-amino-2,3-diphenylimidazo[2,1-a]isoquinoline-6-carbonitriles catalyzed by CuI/l-proline. Under the same reaction conditions, this novel procedure had a good chemoselectivity in cyanacetates for the efficient synthesis of 5-aminoimidazo[2,1-a]isoquinoline-6-carboxylate derivatives in good yields.

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Acknowledgements

This work was financially supported by NSFC of China (No. 21702078), Natural Science Foundation of Jiangsu Higher Education Institution (17KJA150003), the Priority Academic Program Development of Jiangsu Higher education Institution, and TAPP.

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Authors and Affiliations

  1. School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Mei-Mei Zhang, Wei-Qing Miao & Xiang-Shan Wang

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  1. Mei-Mei Zhang
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  2. Wei-Qing Miao
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  3. Xiang-Shan Wang
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Correspondence to Xiang-Shan Wang.

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Zhang, MM., Miao, WQ. & Wang, XS. Copper/l-proline-catalyzed synthesis of 5-amino-2,3-diphenylimidazo[2,1-a]isoquinolines in the presence of Cs2CO3. Monatsh Chem 150, 681–689 (2019). https://doi.org/10.1007/s00706-018-2344-2

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  • DOI: https://doi.org/10.1007/s00706-018-2344-2

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