Monatshefte für Chemie - Chemical Monthly

, Volume 141, Issue 8, pp 883–888 | Cite as

A facile and expeditious approach for the synthesis of 2-azetidinone derivatives via a multicomponent reaction

Original Paper

Abstract

New organic reactions allow chemical transformations which were previously unknown. Therefore, new reactions are important contributions to progress in the field of organic synthesis. Herein, we are reporting a simple, one-pot, efficient three-component synthesis of novel 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)phenyl]-1-phenylazetidin-2-one derivatives using 4-(2-oxo-2H-chromen-4-ylmethoxy)benzaldehydes, anilines, and chloroacetyl chloride in the presence of triethyl amine as a catalyst under different conditions. Taking into account environmental and economic considerations, the protocol presented here has the merits of simple operation, convenient work-up, being environmentally benign, and providing good yields. The synthesized compounds were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis.

Graphical Abstract

Keywords

Multicomponent reaction One-pot synthesis Coumarin 2-Azetidinones 

References

  1. 1.
    Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley, WeinheimCrossRefGoogle Scholar
  2. 2.
    Ugi I (2001) Pure Appl Chem 73:187CrossRefGoogle Scholar
  3. 3.
    Trost BM (1995) Angew Chem Int Ed 34:259CrossRefGoogle Scholar
  4. 4.
    De Kimpe N (1996) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, p 507CrossRefGoogle Scholar
  5. 5.
    Singh GS, Mmolotsi BJ (2005) Il Farmaco 60:727CrossRefGoogle Scholar
  6. 6.
    Muhammad M, Bhat I (2003) Indian J Heterocycl Chem 13:183Google Scholar
  7. 7.
    Biradar JS, Manjunath SY (2004) Indian J Chem B 43B:141Google Scholar
  8. 8.
    Desai JM, Shah VH (2003) Indian J Chem B 42B:631Google Scholar
  9. 9.
    Banik BK, Becker FF, Banik I (2004) Bioorg Med Chem 12:2523CrossRefGoogle Scholar
  10. 10.
    Anaya J, Gero DS, Grande M, Hernando JIM, Laso NM (1999) Bioorg Med Chem 7:837CrossRefGoogle Scholar
  11. 11.
    Gerona-Navarro G, Perez de Vega MJ, Garcia-Lopez MT, Graciela A, Snoeck R, De Clercq E, Balzarini J, Gonzalez-Muniz R (2005) J Med Chem 48:2612CrossRefGoogle Scholar
  12. 12.
    Gerona-Navarro G, Perez de Vega MJ, Garcıa-Lopez MT, Graciela A, Snoeck R, Balzarini J, De Clercq E, Gonzalez-Muniz R (2004) Bioorg Med Chem Lett 14:2253CrossRefGoogle Scholar
  13. 13.
    Sutton JC, Bolton SA, Harti KS, Huang MH, Jacobs G, Meng W, Zhao G, Bisacchi GS (2004) Bioorg Med Chem Lett 14:2233CrossRefGoogle Scholar
  14. 14.
    Wang Y, Zhang H, Huang W, Kong J, Zhou J, Zhang B (2009) Eur J Med Chem 44:1638CrossRefGoogle Scholar
  15. 15.
    Marchand-Brynaert J, Dive G, Galleni M, Gerard S (2004) Bioorg Med Chem 12:129CrossRefGoogle Scholar
  16. 16.
    Bode W, Meyer EF, Powers JC (1989) Biochemistry 28:1951CrossRefGoogle Scholar
  17. 17.
    Alcaide B, Almendros P (2002) Synlett 381Google Scholar
  18. 18.
    Castagnolo D, Armaroli S, Corelli F, Botta M (2004) Tetrahedron Asymmetr 15:941CrossRefGoogle Scholar
  19. 19.
    Hosamani KM, Hiremath VB, Keri RS, Harisha RS, Hallagudi SB (2008) Can J Chem 86:1030CrossRefGoogle Scholar
  20. 20.
    Alcaide B, Almendros P (2002) Curr Med Chem 6:245Google Scholar
  21. 21.
    Furman B, Borsuk K, Kaluza Z, Lysek R, Chemielewski M (2004) Curr Med Chem 8:463Google Scholar
  22. 22.
    Keri RS, Hosamani KM, Shingalapur RV, Seetharama Reddy HR (2009) Eur J Med Chem 44:5123CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.P.G. Department of Studies in ChemistryKarnatak UniversityDharwadIndia

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