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

  • Mei-Mei Zhang
  • Wei-Qing Miao
  • Xiang-Shan WangEmail author
Original Paper

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.

Graphical abstract

Keywords

Imidazoisoquinoline α-Arylation CuI Synthesis 

Notes

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.

Supplementary material

706_2018_2344_MOESM1_ESM.docx (1.2 mb)
Supplementary material 1 (DOCX 1266 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional MaterialsJiangsu Normal UniversityXuzhouPeople’s Republic of China

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