Skip to main content
SpringerLink
Log in

Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A new protocol has been developed for the diastereoselective synthesis of 1,3-cyclohexadienes using vinyl malononitriles, dibenzalacetones and NaH as reagents in THF. This transformation is comprised of interesting steps like Michael addition, cyclization and ring-opening reactions.

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

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  1. Watanabe CMH, Bench BJUS (2007) Chem Abstr 147:427217

    Google Scholar 

  2. Gein VL, Gein NV, Voronina ÉV, Kriven’ko AP (2002) Pharm Chem J 36:131

    Article  CAS  Google Scholar 

  3. Urbahns K, Mauler FDE (1997) Chem Abstr 127:307213

    Google Scholar 

  4. Bench BJ, Liu C, Evett CR, Watanabe CMH (2006) J Org Chem 71:9458

    Article  CAS  PubMed  Google Scholar 

  5. Bench BJ, Tichy SE, Perez LM, Benson J, Watanabe CMH (2008) Bioorg Med Chem Lett 16:7573

    Article  CAS  Google Scholar 

  6. Fishkin N, Pescitelli G, Sparrow JR, Nakanishi K, Berova N (2004) Chirality 16:637

    Article  CAS  PubMed  Google Scholar 

  7. Fishkin N, Sparrow JR, Allikmets R, Nakanishi K (2005) Proc Natl Acad Sci USA 102:7091

    Article  CAS  PubMed  Google Scholar 

  8. Levandowski BJ, Houk KN (2015) J Org Chem 80:3530

    Article  CAS  PubMed  Google Scholar 

  9. González-Béjar M, Bentama A, Miranda MA, Stiriba SE, Pérez-Prieto P (2007) J Org Lett 9:2067

    Article  CAS  Google Scholar 

  10. Du G, Long Y, Xue J, Zhang S, Dong Y, Li X (2015) Macromolecules 48:1627

    Article  CAS  Google Scholar 

  11. Zhan G, He Q, Yuan X, Chen YC (2014) Org Lett 16:6000

    Article  CAS  PubMed  Google Scholar 

  12. Babu TH, Karthik K, Perumal PT (2010) Synlett 7:1128

    Google Scholar 

  13. Xue D, Li J, Zhang ZT, Deng JG (2007) J Org Chem 72:5443

    Article  CAS  PubMed  Google Scholar 

  14. Elinson MN, Ilovaisky AI, Merkulova VM, Barba F, Batanero B (2013) Tetrahedron 69:7125

    Article  CAS  Google Scholar 

  15. Chen YC, Xue D, Deng JG, Cui X, Zhu J, Jiang YZ (2004) Tetrahedron Lett 45:1555

    Article  CAS  Google Scholar 

  16. Xie JW, Chen W, Li R, Zeng M, Du W, Yue L, Chen YC, Wu Y, Zhu J, Deng JG (2007) Angew Chem Int Ed 46:389

    Article  Google Scholar 

  17. Lu J, Liu F, Zhou WJ, Loh TP (2008) Tetrahedron Lett 49:5389

    Article  CAS  Google Scholar 

  18. Poulsen TB, Alemparte C, Jørgensen KA (2005) J Am Chem Soc 127:11614

    Article  CAS  PubMed  Google Scholar 

  19. Babu TH, Joseph AA, Muralidharan D, Perumal PT (2010) Tetrahedron Lett 51:994

    Article  CAS  Google Scholar 

  20. Su W, Ding K, Chen Z (2009) Tetrahedron Lett 50:636

    Article  CAS  Google Scholar 

  21. Attanasi OA, Favi G, Geronikaki A, Mantellini F, Moscatelli G, Paparisva A (2013) Org Lett 15:2624

    Article  CAS  PubMed  Google Scholar 

  22. Alizadeh A, Sedighian H, Bayat F (2014) Synlett 25:389

    Article  CAS  Google Scholar 

  23. Alizadeh A, Sedighian H, Ghanbaripour R (2014) Helv Chim Acta 97:447

    Article  CAS  Google Scholar 

  24. Alizadeh A, Sedighian H, Hosseini SY, Zhu LG (2015) Helv Chim Acta 98:569

    Article  CAS  Google Scholar 

  25. Alizadeh A, Sedighian H, Hosseini SY, Bayat F (2015) Helv Chim Acta 98:1426

    Article  CAS  Google Scholar 

  26. Alizadeh A, Sedighian H, Hosseini SY, Bayat F, Zhu Z, Dusek M (2015) Tetrahedron 71:7885

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Abdolali Alizadeh, Akram Bagherinejad, Fahimeh Bayat & Seyed Yasub Hosseini

  2. Department of Chemistry, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Long-Guan Zhu

Authors
  1. Abdolali Alizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akram Bagherinejad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fahimeh Bayat
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Seyed Yasub Hosseini
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Long-Guan Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abdolali Alizadeh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2294 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alizadeh, A., Bagherinejad, A., Bayat, F. et al. Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies. Mol Divers 23, 651–656 (2019). https://doi.org/10.1007/s11030-018-9900-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-018-9900-x

Keywords

Search

Navigation