Synthesis 2012; 44(9): 1380-1384
DOI: 10.1055/s-0031-1290884
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot, Pseudo Five-Component Synthesis of Spirooxindole Derivatives Containing Fused 1,4-Dihydropyridines in Water

Abdolali Alizadeh*
Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran, Fax: +98(21)88006544   Email: abdol_alizad@yahoo.com   Email: aalizadeh@modares.ac.ir
,
Azadeh Mikaeili
Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran, Fax: +98(21)88006544   Email: abdol_alizad@yahoo.com   Email: aalizadeh@modares.ac.ir
,
Tahereh Firuzyar
Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran, Fax: +98(21)88006544   Email: abdol_alizad@yahoo.com   Email: aalizadeh@modares.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 16 December 2011

Accepted after revision: 19 March 2012

Publication Date:
11 April 2012 (online)


Abstract

An efficient, facile, and simple route for the preparation of spirooxindole-containing fused 1,4-dihydropyridine derivatives through a one-pot, pseudo five-component condensation reaction of isatin or its derivatives, 1,1-bis(methylthio)-2-nitroethylene, 1,3-dicarbonyl compounds, and two equivalents of ammonia in water is reported. The merits of this method include the use of water as a green solvent, and inexpensive and easily available starting materials and catalyst, the high yield of products, and the straightforward work-up.

 
  • References

  • 1 Ahadi S, Ghahremanzadeh R, Mirzaei P, Bazgir A. Tetrahedron 2009; 65: 9316
  • 2 Rajabi Khorrami A, Faraji F, Bazgir A. Ultrason. Sonochem. 2011; 18: 635
  • 3 Rajab Khorrami A, Faraji F, Bazgir A. Ultrason. Sonochem. 2010; 17: 587
  • 4 Poornachandran M, Raghunathan R. Tetrahedron 2006; 62: 11274
    • For early surveys of oxindole alkaloids, see:

    • 5a Cordell GA. An Introduction to Alkaloids, In A Biogenetic Approach . Wiley-Interscience; New York: 1981
    • 5b Bindra JS. The Alkaloids-Chemistry and Physiology . Oxindole Alkaloids . Vol. 14. Manske RH. F. Academic; New York: 1973: 83
    • For reviews of gelsemium alkaloids, see:

    • 6a Liu ZJ, Lu RR. The Alkaloids 1988; 33: 83
    • 6b Saxton JE. The Alkaloids 1965; 8: 93
    • 7a Chang MY, Pai CL, Kung YH. Tetrahedron Lett. 2005; 46: 8463
    • 7b Baran SP, Richter RM. J. Am. Chem. Soc. 2005; 127: 15394
    • 7c Hilton ST, Ho TC, Pljevaljcic G, Jones K. Org. Lett. 2000; 2: 2639
    • 7d Cui CB, Kakeya H, Okada G, Onose R, Osada H. J. Antibiot. 1996; 49: 527
    • 8a Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B. J. Org. Chem. 1991; 56: 6527
    • 8b Ghosal S, Banerjee PK. Indian J. Chem. 1971; 9: 289
    • 8c Jones K, Wilkinson J. J. Chem. Soc., Chem. Commun. 1992; 1767
    • 8d Bascop SI, Sapi J, Laronze JY, Levy J. Heterocycles 1994; 38: 725
    • 8e Pellegrini C, Strassler C, Weber M, Borschberg HJ. Tetrahedron: Asymmetry 1994; 5: 1979
    • 8f Palmisano G, Annunziata R, Papeo G, Sisti M. Tetrahedron: Asymmetry 1996; 7: 1
    • 10a Buhler FR, Kiowski W. J. Hypertens. 1987; S3: 5
    • 10b Reid JL, Meredith PA, Pasanisi F. J. Cardiovasc. Pharmacol. 1985; S18: 7
  • 11 Janis RA, Silver PJ, Triggle DJ. Adv. Drug Res. 1987; 16: 309
  • 12 Alizadeh A, Firuzyar T, Mikaeili A. Synthesis 2010; 3913
  • 13 Alizadeh A, Sabahnoo H, Noaparast Z, Zohreh N, Mikaeili A. Synlett 2010; 1854
  • 14 Alizadeh A, Noaparast Z, Sabahnoo H, Zohreh N. Synlett 2010; 1469
  • 15 Zohreh N, Alizadeh A, Bijanzadeh HR, Zhu LG. J. Comb. Chem. 2010; 12: 497
  • 16 Alizadeh A, Zohreh N. Helv. Chim. Acta 2010; 93: 1221
  • 17 Alizadeh A, Noaparast Z, Sabahnoo H, Zohreh N. Helv. Chim. Acta 2010; 93: 1401
  • 18 Alizadeh A, Firuzyar T. Tetrahedron 2010; 66: 9835