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


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


Imidazoisoquinoline α-Arylation CuI Synthesis 



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)


  1. 1.
    Xi Q, Wu GZ, Yang N, Shen YH, Tang J, Zhang WD (2018) Biochem Biophys Res Commun 502:202CrossRefGoogle Scholar
  2. 2.
    Mirhadi E, Rezaee M, Malaekeh-Nikouei B (2018) Biomed Pharmacother 104:465CrossRefGoogle Scholar
  3. 3.
    Wang C, Wang H, Zhang Y, Guo W, Long C, Wang J, Liu L, Sun X (2017) Oncol Rep 37:2109CrossRefGoogle Scholar
  4. 4.
    Jin TY, Li SQ, Jin CR, Shan H, Wang RM, Zhou MX, Li AL, Li LY, Hu SY, Shen T, Xiang L (2018) J Nat Prod 81:768CrossRefGoogle Scholar
  5. 5.
    Savarese JJ, Wastila WB (1995) Acta Anaesth Scand 106:91CrossRefGoogle Scholar
  6. 6.
    Li Y, Zuo GY (2010) Chin Tradit Herb Drugs 41:1006Google Scholar
  7. 7.
    Anukumar A, Tamizmani M, Jeganmohan M (2018) J Org Chem 83:8567CrossRefGoogle Scholar
  8. 8.
    Zhang L, Liu Z, Wang R, Jin Y, Xia XF (2018) Synlett 29:1520CrossRefGoogle Scholar
  9. 9.
    Sun Q, Zhang YY, Sun J, Han Y, Jia X, Yan CG (2018) J Org Chem 83:6640CrossRefGoogle Scholar
  10. 10.
    Zhang L, Zhang G, Li Y, Wang S, Lei A (2018) Chem Commun 54:5744CrossRefGoogle Scholar
  11. 11.
    Molina A, Pascual-Escudero A, Adrio J, Carretero JC (2017) J Org Chem 82:11238CrossRefGoogle Scholar
  12. 12.
    Yu Y, Liu Y, Liu A, Xie H, Li H, Wang W (2016) Org Biomol Chem 14:7455CrossRefGoogle Scholar
  13. 13.
    Ma MY, Liu JQ, Wang XS (2017) Tetrahedron 73:4698CrossRefGoogle Scholar
  14. 14.
    Dhiman S, Pericherla K, Nandwana NK, Kumar D, Kumar A (2014) J Org Chem 79:7399CrossRefGoogle Scholar
  15. 15.
    Palucki M, Buchwald SL (1997) J Am Chem Soc 119:11108CrossRefGoogle Scholar
  16. 16.
    Hamann BC, Hartwig JF (1997) J Am Chem Soc 119:12382CrossRefGoogle Scholar
  17. 17.
    Yang BW, Dao PDQ, Yoon NS, Cho CS (2017) J Organomet Chem 851:136CrossRefGoogle Scholar
  18. 18.
    Miao WQ, Liu JQ, Wang XS (2017) Org Biomol Chem 15:5325CrossRefGoogle Scholar
  19. 19.
    Dong F, Pan WC, Liu JQ, Wang XS (2018) Monatsh Chem 149:569CrossRefGoogle Scholar
  20. 20.
    Lee HK, Dao PDQ, Kim Y, Cho CS (2018) Synthesis 50:3248Google Scholar
  21. 21.
    Nandwana NK, Dhiman S, Shelke GM, Kumar S (2016) Org Biomol Chem 14:1736CrossRefGoogle Scholar
  22. 22.
    Lu J, Gong X, Yang H, Fu H (2010) Chem Commun 46:4172CrossRefGoogle Scholar
  23. 23.
    Liu T, Wang R, Yang H, Fu H (2011) Chem Eur J 17:6765CrossRefGoogle Scholar
  24. 24.
    Chen DS, Dou GL, Li YL, Liu Y, Wang XS (2013) J Org Chem 78:5700CrossRefGoogle Scholar
  25. 25.
    Feng BB, Liu JQ, Wang XS (2017) J Org Chem 82:1817CrossRefGoogle Scholar
  26. 26.
    Li C, Zhang WT, Wang XS (2014) J Org Chem 79:5847CrossRefGoogle Scholar

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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