Skip to main content
SpringerLink
Log in

Synthesis of 8-oxoprotoberberines using acid-mediated cyclization or the Heck reaction

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A facile method of synthesizing 8-oxoprotoberberines is described from 6-benzoyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline-5-carbaldehyde via acid-mediated cyclization or from 2-(2-iodophenethyl)isoquinolin-1(2H)-one via the Heck reaction. The present method offers several advantages, such as good yields and a simple procedure.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1

Similar content being viewed by others

References

  1. Matulenko MA, Meyers AI (1996) J Org Chem 61:573

    Article  CAS  Google Scholar 

  2. Meyers AI (1992) Tetrahedron Lett 48:2589

    CAS  Google Scholar 

  3. Vollekova A, Kettmann V (2003) J Phytother Res 17:834

    Article  CAS  Google Scholar 

  4. Grycova L, Dostal J, Marek R (2007) Phytochemistry 68:150

    Article  CAS  Google Scholar 

  5. Hwang JM, Kou HC, Tseng TH (2006) Arch Toxicol 80:62

    Article  CAS  Google Scholar 

  6. Weimar CVA, Silvia W (1991) Arch Pharmacol 324:509

    CAS  Google Scholar 

  7. Boudou M, Enders D (2005) J Org Chem 70:9486

    Article  CAS  Google Scholar 

  8. Memetzidis G, Stambach JF, Jung L (1991) Eur J Med Chem 22:331

    Google Scholar 

  9. Cushman M, Dekow FW, Jacobsen LB (1979) J Med Chem 22:331

    Article  CAS  Google Scholar 

  10. Wilson WD, Gough AN, Doyle JJ (1976) J Med Chem 19:1261

    Article  CAS  Google Scholar 

  11. Cheng CC (1976) J Med Chem 19:882

    Article  Google Scholar 

  12. Somsak R, Werawat L, Pongtip T (1980) Tetrahedron Lett 21:189

    Article  Google Scholar 

  13. Cobas A, Castedo L (1988) Tetrahedron Lett 29:2491

    Article  CAS  Google Scholar 

  14. Cobas A, Castedo L (1992) J Org Chem 57:6765

    Article  CAS  Google Scholar 

  15. Grigg R, Sridharan V, Stevenson P (1990) Tetrahedron 46:4003

    Article  CAS  Google Scholar 

  16. Bombrun A, Sageot O (1997) Tetrahedron 38:1057

    Article  CAS  Google Scholar 

  17. Mann E, Herradon B (2000) Synlett 509

  18. Wakchaure PB, Easwar S, Puranik VG (2008) Tetrahedron 64:1786

    Article  CAS  Google Scholar 

  19. Yang SH, Khadka DB, Kim YC (2009) Tetrahedron 65:10142

    Article  Google Scholar 

  20. Orito K, Satoh Y, Nishizawa H, Harada R (2000) Org Lett 2:2532

    Google Scholar 

  21. Wakchaure PB, Easwar S, Argade NP (2009) Synthesis 1667

  22. Xu JQ, Shen Q, Li J, Hu LH (2010) Bioorg Med Chem 18:3934

    Article  CAS  Google Scholar 

  23. Wang XC, Zhen ZP, Gan XW, Hu LH (2009) Org Lett 11:5522

    Article  CAS  Google Scholar 

  24. Shao Y, Zhang HK, Hu LH (2009) J Nat Prod 72:1170

    Article  CAS  Google Scholar 

  25. Gan XW, Wang W, Hu LH (2009) Org Lett 11:589

    Article  CAS  Google Scholar 

  26. Zhang YN, Zhang SL, Ma L, Hu LH (2008) Adv Synth Catal 350:2373

    Article  CAS  Google Scholar 

  27. Zhang YN, Zhang W, Hu LH (2008) Bioorg Med Chem 16:8697

    Article  CAS  Google Scholar 

  28. Turner N, Hu LH, Ye JM (2008) Diabetes 57:1414

    Article  CAS  Google Scholar 

  29. Cheng Z, Chen AF, Hu LH, Li JY, Li J (2010) Bioorg Med Chem 18:5915

    Article  CAS  Google Scholar 

  30. Zalan Z, Martinek TA (2006) Tetrahedron 62:2883

    Article  CAS  Google Scholar 

  31. Wang YQ (2003) Org Lett 5:2931

    Article  Google Scholar 

  32. Endo A, Yanagisawa A, Fukuyama T (2002) J Am Chem Soc 124:6552

    Article  CAS  Google Scholar 

  33. Yao Q, Kinney EP, Yang Z (2003) J Org Chem 68:7528

    Article  CAS  Google Scholar 

  34. Thanh NL, Seong GG, Cho WJ (2004) J Org Chem 69:2768

    Article  Google Scholar 

  35. Lenz GR (1974) J Org Chem 39:2846

    Article  CAS  Google Scholar 

  36. Emmanoel VS, Elaine CC (2010) J Nat Prod 73:1180

    Article  Google Scholar 

  37. Ye ZQ, Zhou QT (1997) Acta Chim Sinica 55:202

    Google Scholar 

Download references

Acknowledgments

This work was supported by the Chinese National Science & Technology Major Project “Key New Drug Creation and Manufacturing Program” (grants 2009ZX09301-001 and 2009ZX09102-022), the National Natural Science Foundation of China (grants 30925040, 90713046, 30772638, and U0633008), CAS Foundation (grants KSCX2-YW-R-168 and KSCX2-YW-R-179), Shanghai Commission of Science and Technology (grants 08DZ2291300, 09DZ2291200, and 09431902100) and the National Hi-Tech Research and Development Program Grant of China (grants 2007AA09Z402, 2007AA02Z147, and 2008AA02Z105).

Author information

Authors and Affiliations

  1. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People’s Republic of China

    Anfeng Chen, Kun Zhao, Hankun Zhang, Xianwen Gan, Min Lei & Lihong Hu

Authors
  1. Anfeng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kun Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hankun Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xianwen Gan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Min Lei
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Lihong Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Min Lei or Lihong Hu.

Additional information

A. Chen and K. Zhao contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, A., Zhao, K., Zhang, H. et al. Synthesis of 8-oxoprotoberberines using acid-mediated cyclization or the Heck reaction. Monatsh Chem 143, 825–830 (2012). https://doi.org/10.1007/s00706-011-0656-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0656-6

Keywords

Search

Navigation