Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 9, pp 917–921 | Cite as

A regioselective and diastereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition of stable isatin ketonitrone and various dipolarophiles

  • Morteza Mehrdad
  • Laleh Faraji
  • Khosrow Jadidi
  • Parisa Eslami
  • Hossein Sureni
Original Paper

Abstract

The 1,3-dipolar cycloaddition of stable isatin ketonitrone with various dipolarophiles has been conducted under classical, ionic liquid, and solvent-free conditions to give novel spiro[oxindole-isoxazolidine] derivatives with similar diastereoselectivity. In the presence of the ionic liquid 1-butyl-3-methylimidazolium bromide highly diastereoselective and regioselective cyclocondensation products were obtained in good to excellent yields in the absence of any catalyst. The reaction workup was simple and the ionic liquid was easily recovered from the reaction and reused.

Graphical abstract

Keywords

Isatin ketonitrone 1,3-Dipolar cycloaddition Ionic liquids Spiro[oxindole-isoxazolidine] derivatives 

References

  1. 1.
    Kissane M, Lawrence SE, Maguire AR (2010) Tetrahedron 66:4564CrossRefGoogle Scholar
  2. 2.
    Grigor’ev IA (2008) In: Feuer H (ed), Nitrile oxides, nitrones, and nitronates in organic synthesis: novel strategies in synthesis, 2nd edn. Wiley, HobokenGoogle Scholar
  3. 3.
    Gothelf KV, Jorgensen KA (1998) Chem Rev 98:863CrossRefGoogle Scholar
  4. 4.
    Torssell KGB (1988) Nitrile oxides, nitrones, and nitronates in organic synthesis: novel strategies in synthesis. VCH, New YorkGoogle Scholar
  5. 5.
    Tufariello JJ (1984) In: Padwa A (ed), 1,3-Dipolar cycloaddition chemistry. Wiley, New YorkGoogle Scholar
  6. 6.
    Macdonald JM, Horsley HT, Ryan JH, Saubern S, Holmes AB (2008) Org Lett 10:4227CrossRefGoogle Scholar
  7. 7.
    Voinov MA, Shevelev TG, Rybalova TV, Gatilov YV, Pervukhina NV, Burdukov AB, Grigor’ev IA (2007) Organometallics 26:1607CrossRefGoogle Scholar
  8. 8.
    Pfeiffer JY, Beauchemin AM (2009) J Org Chem 74:8381CrossRefGoogle Scholar
  9. 9.
    Fischer R, Hyrosova E, Fisera L, Hametner C, Cyranski MK (2005) Chem Pap 59:275Google Scholar
  10. 10.
    Tomioka Y, Nagahiro C, Nomura Y, Maruoka H (2003) J Heterocycl Chem 40:121CrossRefGoogle Scholar
  11. 11.
    Torrente S, Noya B, Branchadell V, Alonso R (2003) J Org Chem 68:4772CrossRefGoogle Scholar
  12. 12.
    Hulsbos E, Marcus J, Brussee J, van der Gen A (1997) Tetrahedron Asymmetry 8:1061CrossRefGoogle Scholar
  13. 13.
    Franco S, Merchan FL, Merino P, Tejero T (1995) Synth Commun 25:2275CrossRefGoogle Scholar
  14. 14.
    Black DSC, Johnstone LM (1984) Aust J Chem 37:117CrossRefGoogle Scholar
  15. 15.
    Exner O (1951) Collect Czech Chem Commun 16:258Google Scholar
  16. 16.
    Suman Reddy Y, Kadigachalam P, Doddi VR, Vankar YD (2009) Tetrahedron Lett 50:5827CrossRefGoogle Scholar
  17. 17.
    Tacconi G, Righetti PP, Desimoni G (1980) J Prakt Chem 322:679CrossRefGoogle Scholar
  18. 18.
    Aurich HG, Weiss W (1976) Tetrahedron 32:159CrossRefGoogle Scholar
  19. 19.
    Takeuchi Y, Furusaki F (1977) Adv Heterocycl Chem 21:207CrossRefGoogle Scholar
  20. 20.
    Frederickson M (1997) Tetrahedron 53:403CrossRefGoogle Scholar
  21. 21.
    Mzengeza S, Whitney RA (1988) J Org Chem 53:4074CrossRefGoogle Scholar
  22. 22.
    Mzengeza S, Yang CM, Whitney RA (1987) J Am Chem Soc 109:276CrossRefGoogle Scholar
  23. 23.
    Kasahara K, Iida H, Kibayashi C (1989) J Org Chem 54:2225CrossRefGoogle Scholar
  24. 24.
    Iida H, Kasahara K, Kibayashi C (1986) J Am Chem Soc 108:4647CrossRefGoogle Scholar
  25. 25.
    Ooi H, Urushibara A, Esumi T, Iwabuchi Y, Hatakeyama S (2001) Org Lett 3:953CrossRefGoogle Scholar
  26. 26.
    Rong J, Roselt P, Plavec J, Chattopadhyaya J (1994) Tetrahedron 50:4921CrossRefGoogle Scholar
  27. 27.
    Damavandy JA, Mehrdad M (1990) J Sci Islamic Repub Iran 1:96Google Scholar
  28. 28.
    Bigdeli MA, Mehrdad M (1991) Iran J Chem Chem Eng 10:101Google Scholar
  29. 29.
    Bigdeli MA, Mehrdad M (1993) J Sci Islamic Repub Iran 4:109Google Scholar
  30. 30.
    Jadidi K, Ghahremanzadeh R, Mehrdad M, Ghanbari M, Arvin-Nezhad H (2008) Monatsh Chem 139:277CrossRefGoogle Scholar
  31. 31.
    Jadidi K, Gharemanzadeh R, Mehrdad M, Darabi HR, Khavasi HR, Asgari D (2008) Ultrason Sonochem 15:124CrossRefGoogle Scholar
  32. 32.
    Jadidi K, Ghahremanzadeh R, Bazgir A (2009) Tetrahedron 65:2005CrossRefGoogle Scholar
  33. 33.
    Anastas PT, Kirchhoff MM (2002) Acc Chem Res 35:686CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Morteza Mehrdad
    • 1
  • Laleh Faraji
    • 2
  • Khosrow Jadidi
    • 2
  • Parisa Eslami
    • 2
  • Hossein Sureni
    • 2
  1. 1.Department of Environmental Pollution, Environmental Sciences Research InstituteShahid Beheshti UniversityTehranIran
  2. 2.Department of ChemistryShahid Beheshti UniversityTehranIran

Personalised recommendations