Download PDF
Synthesis 2010(22): 3913-3917  
DOI: 10.1055/s-0030-1258249
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient One-Pot Synthesis of Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-Diazaheterocycle Fragments via Four-Component Reaction

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

Publication History

Received 16 July 2010
Publication Date:
14 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient, one-pot synthetic protocol toward spirooxindole derivatives containing 1,4-dihydropyridine-fused 1,3-diazaheterocycle fragments, a class of biologically active compounds starting from 1,1-bis(methylthio)-2-nitroethylene, 1,n-diamine, isatin, or its derivatives, and malononitrile is described. The reaction proceeds in ethanol in the presence of 10 mol% of piperidine as a basic catalyst under reflux conditions to produce the title compounds in 74-85% yields.

Key words

spirooxindole - 1,4-dihydropyridine - malononitrile - 1,n-diamine - 1,1-bis(methylthio)-2-nitroethylene - multicomponent reaction

    References

  • 1a Orru RVA. de Greef M. Synthesis  2003,  1471 
    Google Scholar
  • 1b Balme G. Bossharth E. Monteiro N. Eur. J. Org. Chem.  2003,  4101 
    Google Scholar
  • 1c Bräse S. Gil C. Knepper K. Bioorg. Med. Chem.  2002,  10:  2415 
    Google Scholar
  • 1d Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 2 Zhu J. Bienayme H. Multicomponent Reactions   Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 3 de Meijere A. Nüske H. Es-Sayed M. Labahn T. Schroen M. Bräse S. Angew. Chem. Int. Ed.  1999,  38:  3669 
    CrossrefGoogle Scholar
  • 4 Da Silva JFM. Garden SJ. Pinto AC. J. Braz. Chem. Soc.  2001,  273 
    Google Scholar
  • 5a Sannigrahi M. Tetrahedron  1999,  55:  9007 
    Google Scholar
  • 5b Heathcock CH. Graham SL. Pirrung MC. Plavac F. White CT. Spirocyclic Systems In The Total Synthesis of Natural Products   ApSimon J. Wiley; New York: 1983.  p.264 
    Google Scholar
  • 6a Chang M.-Y. Pai C.-L. Kung Y.-H. Tetrahedron Lett.  2005,  46:  8463 
    Google Scholar
  • 6b Baran SP. Richter RM. J. Am. Chem. Soc.  2005,  127:  15394 
    Google Scholar
  • 6c Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett.  2000,  2:  2639 
    Google Scholar
  • 6d Cui C.-B. Kakeya H. Okada G. Onose R. Osada H. J. Antibiot.  1996,  49:  527 
    Google Scholar
  • 7a Fuchs JR. Funk RL. Org. Lett.  2005,  7:  677 
    Google Scholar
  • 7b Yong SR. Ung AT. Pyne SG. Skelton BW. White AH. Tetrahedron  2007,  63:  1191 
    Google Scholar
  • 7c Jiang T. Kuhen KL. Wolff K. Yin H. Bieza K. Caldwell J. Bursulaya B. Wu TY.-H. He Y. Bioorg. Med. Chem. Lett.  2006,  16:  2105 
    Google Scholar
  • 7d Yong SR. Williams MC. Pyne SG. Ung AT. Skelton BW. White AH. Turner P. Tetrahedron  2005,  61:  8120 
    Google Scholar
  • 7e Feldman KS. Vidulova DB. Karatjas AG. J. Org. Chem.  2005,  70:  6429 
    Google Scholar
  • 8a Lavilla R. J. Chem. Soc., Perkin Trans. 1  2002,  1141 
    Google Scholar
  • 8b Sausins A. Duburs G. Heterocycles  1988,  27:  269 
    Google Scholar
  • 9a Mojarrad JS. Vo D. Velázquez C. Knaus EE. Bioorg. Med. Chem.  2005,  13:  4085 
    Google Scholar
  • 9b De Simone RW. Currie KS. Mitchell SA. Darrow JW. Pippin DA. Comb. Chem. High Throughput Screening  2004,  7:  473 
    Google Scholar
  • 9c Triggle DJ. Cell. Mol. Neurobiol.  2003,  23:  293 
    Google Scholar
  • 9d Meguro K. Aizawa M. Sohda T. Kawamatsu Y. Nagaoka A. Chem. Pharm. Bull.  1985,  33:  3787 
    Google Scholar
  • 10a Achiwa K. Kato T. Curr. Org. Chem.  1999,  3:  77 
    Google Scholar
  • 10b Bossert F. Vater W. Med. Res. Rev.  1989,  9:  291 
    Google Scholar
  • 10c Stout DM. Meyers AI. Chem. Rev.  1982,  82:  223 
    Google Scholar
  • 11a Zohreh N. Alizadeh A. Bijanzadeh HR. Zhu LG. J. Comb. Chem.  2010,  12:  497 
    Google Scholar
  • 11b Rostamnia S. Alizadeh A. Zhu L.-G. J. Comb. Chem.  2009,  11:  143 
    Google Scholar
  • 11c Alizadeh A. Rezvanian A. Tetrahedron  2010,  66:  6924 
    Google Scholar
  • 11d Alizadeh A. Noaparast Z. Sabahnoo H. Zohreh N. Synlett  2010,  1496 
    Google Scholar
  • 11e Alizadeh A. Sabahnoo H. Noaparast Z. Zohreh N. Mikaeili A. Synlett  2010,  1854 
    Google Scholar
  • 11f Alizadeh A. Rostamnia S. Zhu LG. Tetrahedron Lett.  2010,  51:  4750 
    Google Scholar