Skip to main content
SpringerLink
Log in

4-dimethylaminopyridine-catalyzed cascade reaction for efficient synthesis of naphthofurans

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A convenient and efficient method was developed for the synthesis of naphtho[2,1-b]furans via 4-dimethylaminopyridine(DMAP)-catalyzed cascade reaction of 2-hydroxy-1-naphthaldehydes and α-halogenated ketones in moderate to good yields in the presence of Na2CO3 at 80 ºC for 6 h. The mechanism for this process was briefly discussed with a tentative catalytic cycle proposed. Moreover, this method features organocatalysts and high step-economy, which make it practical and attractive.

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

Similar content being viewed by others

References

  1. Srivastava V., Negi A. S., Kumar J. K., Faridi U., Sisodia B. S., Darokar M. P., Luqman S., Khanuja S. P. S., Bioorg. Med. Chem. Lett., 2006, 16(4), 911

    Article  CAS  Google Scholar 

  2. Rao V. K., Shelke G. M., Tiwari R., Parang K., Kumar A., Org. Lett., 2013, 15(9), 2190

    Article  CAS  Google Scholar 

  3. Le Guével R., Oger F., Lecorgne A., Dudasova Z., Chevance S., Bondon A., Barath P., Simonneaux G., Salbert G., Bioorg. Med. Chem., 2009, 17(19), 7021

    Article  Google Scholar 

  4. Gan C. S., Nan D. D., Qiao J. P., Wang C. W., Zhou J. N., J. Nucl. Med., 2012, 53(Sup.1), 1620

    Google Scholar 

  5. Zeni G., Larock R. C., Chem. Rev., 2006, 106(11), 4644

    Article  CAS  Google Scholar 

  6. Patil N. T., Yamamoto Y., Chem. Rev., 2008, 108(8), 3395

    Article  CAS  Google Scholar 

  7. Butin A. V., Melchin V. V., Abaev V. T., Bender W., Pilipenko A. S., Krapivin G. D., Tetrahedron, 2006, 62(34), 8045

    Article  CAS  Google Scholar 

  8. Park K. K., Jeong J., Tetrahedron, 2005, 61(3), 545

    Article  CAS  Google Scholar 

  9. Guo X., Yu R., Li H., Li Z., J. Am. Chem. Soc., 2009, 131(47), 17387

    Article  CAS  Google Scholar 

  10. Lingam V. S. P. R., Dahale D. H., Mukkanti K., Gopalan B., Thomas A., Tetrahedron Lett., 2012, 53(42), 5695

    Article  Google Scholar 

  11. Hou C. D., Xu X. L., An J. Z., Jia X. D., Wang X. C., Wang C., J. Org. Chem., 2012, 77(18), 8310

    Article  Google Scholar 

  12. Hou C. D., An J. Z., Xu X. L., Jia X. D., Wang X. C., Kang L. S., Tetrahedron Lett., 2013, 54(9), 1145

    Article  Google Scholar 

  13. France S., Guerin D. J., Miller S. J., Lectka T., Chem. Rev., 2003, 103(8), 2985

    Article  CAS  Google Scholar 

  14. Tian S. K., Chen Y. G., Hang J., Tang L., McDaid P., Deng L., Acc. Chem. Res., 2004, 37(8), 621

    Article  CAS  Google Scholar 

  15. Jin L. L., Lei Y. T., Chem. Res. Chinese Universities, 2013, 29(4), 710

    Article  CAS  Google Scholar 

  16. Liu Z. M., Fang J., Yan C. G., Chem. Res. Chinese Universities, 2013, 29(6), 1089

    Article  CAS  Google Scholar 

  17. Shang Y. J., Wang C. E., He X. W., Ju K., Zhang M., Yu S. Y., Wu J. P., Tetrahedron, 2010, 66(50), 9629

    Article  CAS  Google Scholar 

  18. Wu J. P., Shang Y. J., Wang C. E., He X. W., Yan Z. L., Hu M. M., Zhou F. Y., RSC Adv., 2013, 3(14), 4643

  19. Kar S., Lahiri S., Chem. Commun., 1995, (9), 957

    Article  Google Scholar 

  20. Rao M. L. N., Awasthi D. K., Banerjee D., Tetrahedron Lett., 2007, 48(3), 431

    Article  CAS  Google Scholar 

  21. Jakub S., Jan S., Heterocycl. Commun., 1999, 5(4), 349

    Google Scholar 

  22. Axelle A., Frédérique T., Gérald G., Synthesis, 1999, (7), 1241

    Google Scholar 

  23. Naskar S., Banerjee M., Hazra A., Mondal S., Maity A., Paira R., Sahu K. B., Saha P., Banerjee S., Mondal N. B., Tetrahedron Lett., 2011, 52, 1527

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Material Engineering, Wuhu Institute of Technology, Wuhu, 241003, P. R. China

    Chenli Fan

  2. Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241000, P. R. China

    Chenli Fan, Xinwei He, Kaisheng Liao, Cui’e Wang & Yongjia Shang

Authors
  1. Chenli Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xinwei He
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kaisheng Liao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Cui’e Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yongjia Shang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yongjia Shang.

Additional information

Supported by the National Natural Science Foundation of China (Nos.21172001, 21372008), the Program for the New Century Excellent Talents in University of China(No.NCET-10-0004) and the Natural Science Foundation of Anhui Province of China(No.1308085QB39).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fan, C., He, X., Liao, K. et al. 4-dimethylaminopyridine-catalyzed cascade reaction for efficient synthesis of naphthofurans. Chem. Res. Chin. Univ. 32, 62–67 (2016). https://doi.org/10.1007/s40242-016-5245-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-016-5245-0

Keywords

Search

Navigation