Download PDF
Synthesis 2011(21): 3491-3495  
DOI: 10.1055/s-0030-1260208
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free and Efficient Synthesis of Highly Functionalized Cyclohexa-1,3-diene Derivatives via a Novel One-Pot Three-Component Reaction

Abdolali Alizadeh*, Atieh Rezvanian, Javad Mokhtari
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 30 June 2011
Publication Date:
05 September 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A catalyst-free and convenient approach for the preparation of cyclohexa-1,3-dienecarboxylate derivatives is described. This three-component reaction between primary amines, alkyl acetoacetate, and dibenzylideneacetone proceeds under solvent-free condition in good to excellent yields.

Key words

primary amines - alkyl acetoacetate - dibenzylideneacetone - cyclohexa-1,3-dienecarboxylate - solvent-free

    References

  • 1a Watanabe CMH, and Bench BJ. inventors; US  2007,232,813.  ; Chem. Abstr. 2007, 147, 427217
  • 1b Barf T, Hammer K, Luthman M, Lehmann F, and Ringom R. inventors; WO  2004,063,156.  ; Chem. Abstr. 2004, 141, 157124
  • 1c Gein VL. Gein NV. Voronina EV. Kriven’ko AP. J. Pharm. Chem.  2002,  36:  131 
    Google Scholar
  • 2a Mimoun H, and Giersch WK. inventors; EP  0,955,290.  ; Chem. Abstr. 1999, 131, 337203
  • 2b Urbahns K, and Mauler F. inventors; DE  19,612,645.  ; Chem. Abstr. 1997, 127, 307213
  • 3a Morgan AR, and Selman SH. inventors; US  5,563,262.  ; Chem. Abstr. 1996, 125, 300695
  • 3b Urbahns K, Heine H.-G, Junge B, Schohe-Loop R, Wollweber H, Sommermeyer H, Glaser T, Wittka R, and De Vry J.-M.-V. inventors; EP  0,698,597.  ; Chem. Abstr. 1996, 124, 342867
  • 4a Hong BC. Wu MF. Tseng HC. Huang GF. Su CF. Liao J.-H. J. Org. Chem.  2007,  72:  8459 
    Google Scholar
  • 4b Vosburg DA. Weiler S. Sorensen EJ. Angew. Chem. Int. Ed.  1999,  38:  971 
    Google Scholar
  • 4c Maurinsh Y. Schraml J. Winter HD. Blaton N. Peeters O. Lescrinier E. Rozenski J. Aerschot AV. Clercq ED. Busson R. Herdewijn P. J. Org. Chem.  1997,  62:  2861 
    Google Scholar
  • 5a Davies SG. Bhalay G. Tetrahedron: Asymmetry  1996,  7:  1595 
    Google Scholar
  • 5b Urones JG. Marcos IS. Basabe P. Diez D. Garrido NM. Phytochemistry  1994,  35:  713 
    Google Scholar
  • 6 Patai S. Rappoport Z. The Chemistry of Dienes and Polyenes   Vol. 1:  Rappoport Z. Wiley; Chichester: 1997. 
    Google Scholar
  • 7a Hong BC. Wu M.-F. Tseng HC. Liao J.-H. Org. Lett.  2006,  8:  2217 
    Google Scholar
  • 7b Newman LM. Garcia H. Hudlicky T. Selifonov SA. Tetrahedron  2004,  60:  729 
    Google Scholar
  • 7c Stratakis M. Stavroulakis M. Sofikiti N. J. Phys. Org. Chem.  2003,  16:  16 
    Google Scholar
  • 8a Xi Z. Li Z. Umeda C. Guan H. Li P. Kotora M. Takahashi T. Tetrahedron  2002,  58:  1107 
    Google Scholar
  • 8b Saito S. Sone T. Murase M. Yamamoto H. J. Am. Chem. Soc.  2000,  122:  10216 
    Google Scholar
  • 9a Dömling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 9b Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 9c Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 10a Alizadeh A. Rezvanian A. Synlett  2011,  1105 
    Google Scholar
  • 10b Alizadeh A. Zarei A. Rezvanian A. Synthesis  2011,  497 
    Google Scholar
  • 10c Alizadeh A. Mokhtari J. Tetrahedron  2011,  67:  3567 
    Google Scholar
  • 10d Alizadeh A. Rezvanian A. Zhu LG. Tetrahedron  2010,  66:  6924 
    Google Scholar
  • 10e Alizadeh A. Rezvanian A. Yuan D. Tetrahedron  2010,  66:  9933 
    Google Scholar
  • 11 Greenhill JV. Chem. Soc. Rev.  1977,  6:  277 
    CrossrefGoogle Scholar
  • 12 Lue P. Greenhill JV. Adv. Heterocycl. Chem.  1996,  67:  207 
    Google Scholar
  • 13 Elassar AZA. El-Khair AA. Tetrahedron  2003,  59:  8463 
    CrossrefGoogle Scholar
  • 14 Negri G. Kascheres C. Kascheres AJ. J. Heterocycl. Chem.  2004,  41:  461 
    CrossrefGoogle Scholar
  • 15 Stanovnik B. Svete J. Chem. Rev.  2004,  104:  2433 
    CrossrefPubMedGoogle Scholar