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Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies

  • Abdolali Alizadeh
  • Akram Bagherinejad
  • Fahimeh Bayat
  • Seyed Yasub Hosseini
  • Long-Guan Zhu
Original Article
  • 11 Downloads

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

Keywords

1,3-Cyclohexadienes Vinyl malononitriles Dibenzalacetones Michael addition Cyclization Ring-opening reaction 

Supplementary material

11030_2018_9900_MOESM1_ESM.doc (2.2 mb)
Supplementary material 1 (DOC 2294 kb)

References

  1. 1.
    Watanabe CMH, Bench BJUS (2007) Chem Abstr 147:427217Google Scholar
  2. 2.
    Gein VL, Gein NV, Voronina ÉV, Kriven’ko AP (2002) Pharm Chem J 36:131CrossRefGoogle Scholar
  3. 3.
    Urbahns K, Mauler FDE (1997) Chem Abstr 127:307213Google Scholar
  4. 4.
    Bench BJ, Liu C, Evett CR, Watanabe CMH (2006) J Org Chem 71:9458CrossRefPubMedGoogle Scholar
  5. 5.
    Bench BJ, Tichy SE, Perez LM, Benson J, Watanabe CMH (2008) Bioorg Med Chem Lett 16:7573CrossRefGoogle Scholar
  6. 6.
    Fishkin N, Pescitelli G, Sparrow JR, Nakanishi K, Berova N (2004) Chirality 16:637CrossRefPubMedGoogle Scholar
  7. 7.
    Fishkin N, Sparrow JR, Allikmets R, Nakanishi K (2005) Proc Natl Acad Sci USA 102:7091CrossRefPubMedGoogle Scholar
  8. 8.
    Levandowski BJ, Houk KN (2015) J Org Chem 80:3530CrossRefPubMedGoogle Scholar
  9. 9.
    González-Béjar M, Bentama A, Miranda MA, Stiriba SE, Pérez-Prieto P (2007) J Org Lett 9:2067CrossRefGoogle Scholar
  10. 10.
    Du G, Long Y, Xue J, Zhang S, Dong Y, Li X (2015) Macromolecules 48:1627CrossRefGoogle Scholar
  11. 11.
    Zhan G, He Q, Yuan X, Chen YC (2014) Org Lett 16:6000CrossRefPubMedGoogle Scholar
  12. 12.
    Babu TH, Karthik K, Perumal PT (2010) Synlett 7:1128Google Scholar
  13. 13.
    Xue D, Li J, Zhang ZT, Deng JG (2007) J Org Chem 72:5443CrossRefPubMedGoogle Scholar
  14. 14.
    Elinson MN, Ilovaisky AI, Merkulova VM, Barba F, Batanero B (2013) Tetrahedron 69:7125CrossRefGoogle Scholar
  15. 15.
    Chen YC, Xue D, Deng JG, Cui X, Zhu J, Jiang YZ (2004) Tetrahedron Lett 45:1555CrossRefGoogle Scholar
  16. 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 46:389CrossRefGoogle Scholar
  17. 17.
    Lu J, Liu F, Zhou WJ, Loh TP (2008) Tetrahedron Lett 49:5389CrossRefGoogle Scholar
  18. 18.
    Poulsen TB, Alemparte C, Jørgensen KA (2005) J Am Chem Soc 127:11614CrossRefPubMedGoogle Scholar
  19. 19.
    Babu TH, Joseph AA, Muralidharan D, Perumal PT (2010) Tetrahedron Lett 51:994CrossRefGoogle Scholar
  20. 20.
    Su W, Ding K, Chen Z (2009) Tetrahedron Lett 50:636CrossRefGoogle Scholar
  21. 21.
    Attanasi OA, Favi G, Geronikaki A, Mantellini F, Moscatelli G, Paparisva A (2013) Org Lett 15:2624CrossRefPubMedGoogle Scholar
  22. 22.
    Alizadeh A, Sedighian H, Bayat F (2014) Synlett 25:389CrossRefGoogle Scholar
  23. 23.
    Alizadeh A, Sedighian H, Ghanbaripour R (2014) Helv Chim Acta 97:447CrossRefGoogle Scholar
  24. 24.
    Alizadeh A, Sedighian H, Hosseini SY, Zhu LG (2015) Helv Chim Acta 98:569CrossRefGoogle Scholar
  25. 25.
    Alizadeh A, Sedighian H, Hosseini SY, Bayat F (2015) Helv Chim Acta 98:1426CrossRefGoogle Scholar
  26. 26.
    Alizadeh A, Sedighian H, Hosseini SY, Bayat F, Zhu Z, Dusek M (2015) Tetrahedron 71:7885CrossRefGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2018

Authors and Affiliations

  • Abdolali Alizadeh
    • 1
  • Akram Bagherinejad
    • 1
  • Fahimeh Bayat
    • 1
  • Seyed Yasub Hosseini
    • 1
  • Long-Guan Zhu
    • 2
  1. 1.Department of ChemistryTarbiat Modares UniversityTehranIran
  2. 2.Department of ChemistryZhejiang UniversityHangzhouPeople’s Republic of China

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