Skip to main content
SpringerLink
Log in

FeCl3-catalyzed multicomponent synthesis of 8-alkoxycarbonylnaphthyl-functionalized pyrazolo[3,4-b]pyridines involving C–C bond cleavage

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

Abstract

An efficient multicomponent reaction for the synthesis of novel 8-alkoxycarbonylnaphthyl-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles, β-ketoesters, actenaphthylene-1,2-dione, and aliphatic alcohol in the presence of inexpensive and environmentally friendly iron(III) chloride is described. It is a fascinating example for the direct conversion of actenaphthylene-1,2-dione to naphthoic ester fragment via C–C bond cleavage reaction.

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

Similar content being viewed by others

References

  1. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Acc Chem Res 29:123

    Article  CAS  Google Scholar 

  2. Liu YY, Wang H, Wan JP (2013) Asian J Org Chem 2:374

    Article  CAS  Google Scholar 

  3. Wan JP, Liu YY (2012) RSC Adv 2:9763

    Article  CAS  Google Scholar 

  4. Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  Google Scholar 

  5. Allais C, Grassot JM, Rodriguez J, Constantieux T (2014) Chem Rev 114:10829

    Article  CAS  Google Scholar 

  6. Dodiya DK, Trivedi AR, Kataria VB, Shah VH (2012) Curr Org Chem 16:400

    Article  CAS  Google Scholar 

  7. Manetti F, Schenone S, Bondavalli F, Brullo C, Bruno O, Ranise A, Mosti L, Menozzi G, Fossa P, Trincavelli ML, Martini C, Martinelli A, Tintori C, Botta M (2005) J Med Chem 48:7172

    Article  CAS  Google Scholar 

  8. Williams M (1983) J Med Chem 26:619

    Article  CAS  Google Scholar 

  9. Placheta P, Karobath M (1980) Eur J Pharmacol 62:225

    Article  CAS  Google Scholar 

  10. Patel JB, Malick JB (1982) Eur J Pharmacol 78:323

    Article  CAS  Google Scholar 

  11. Gunasekaran P, Indumathi S, Perumal S (2013) RSC Adv 3:8318

    Article  CAS  Google Scholar 

  12. Jiang B, Zhang G, Ma N, Shi F, Tu SJ, Kaur P, Li GG (2011) Org Biomol Chem 9:3834

    Article  CAS  Google Scholar 

  13. Saleh TS, Eldebss TMA, Albishri HM (2012) Ultrason Sonochem 19:49

    Article  CAS  Google Scholar 

  14. Wu LQ, Ma SY, Yan FL, Yang CY (2010) Monatsh Chem 141:565

    Article  CAS  Google Scholar 

  15. Dabiri M, Tisseh ZN, Nobahar M, Bazgir A (2011) Helv Chim Acta 94:824

    Article  CAS  Google Scholar 

  16. Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P (2010) Ultrason Sonochem 17:447

    Article  CAS  Google Scholar 

  17. Chen H, Shi DQ (2010) J Comb Chem 12:571

    Article  CAS  Google Scholar 

  18. Dabiri M, Tisseh ZN, Bazgir A (2012) Monatsh Chem 143:139

    Article  CAS  Google Scholar 

  19. Hao WJ, Xu XP, Bai HW, Wang SY, Ji SJ (2012) Org Lett 14:4894

    Article  CAS  Google Scholar 

  20. Ahadi S, Ghahremanzadeh R, Mirzaei P, Bazgir A (2009) Tetrahedron 65:9316

    Article  CAS  Google Scholar 

  21. Hao Y, Xu XP, Chen T, Zhao LL, Ji SJ (2012) Org Biomol Chem 10:724

    Article  CAS  Google Scholar 

  22. Dethe DH, Murhade GM, Ghosh S (2015) J Org Chem 80:8367

    Article  CAS  Google Scholar 

  23. Sheldrick GM (2008) Acta Cryst A64:112

    Article  Google Scholar 

  24. Farrugia LJ (1999) J Appl Cryst 32:837

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the support from the Educational Commission of Hubei Province, China (No. B2015132).

Author information

Authors and Affiliations

  1. Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002, People’s Republic of China

    Ling Fan, Chaochao Yao & Xianhong Wei

Authors
  1. Ling Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chaochao Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xianhong Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ling Fan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2010 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fan, L., Yao, C. & Wei, X. FeCl3-catalyzed multicomponent synthesis of 8-alkoxycarbonylnaphthyl-functionalized pyrazolo[3,4-b]pyridines involving C–C bond cleavage. Monatsh Chem 147, 1597–1603 (2016). https://doi.org/10.1007/s00706-016-1656-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1656-3

Keywords

Search

Navigation