Synlett 2009(16): 2713-2714  
DOI: 10.1055/s-0029-1217967
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Methyl Acetoacetate: A Useful Reagent in Multicomponent Reactions

Tasneem Parvin
Department of Chemistry, Indian Institute of Technology Guwa­hati, Guwahati-781 039, India
e-Mail: t.parvin@iitg.ernet.in;
Further Information

Publication History

Publication Date:
17 September 2009 (online)

Introduction

Methyl acetoacetate is considered as a model β-keto ester, and widely used in various multicomponent reactions for the creation of diverse molecular scaffolds. The dawn of methyl acetoacetate as an important multicomponent substrate began in 1982 by the discovery of Hantzsch’s dihydropyridine synthesis. [¹] The reagent exhibits interesting reactivity pattern in multicomponent reactions depending on the reaction conditions, type of reactions, and involved catalysts. The highly synthetic potential of this easily accessible reagent has found numerous applications, especially in the synthesis of complex heterocyclic structures. [²] An overview of the different reactivity of this versatile substrate in multicomponent reaction is presented below.

    References

  • 1 Hantzsch A. Liebigs Ann. Chem.  1882,  215: 
  • 2 Simon C. Constantieux T. Rodriguez J. Eur. J. Org. Chem.  2004,  4957 
  • 3 Murai K. Nakatani R. Kita Y. Fujioka H. Tetrahedron  2008,  64:  11034 
  • 4 Khan AT. Parvin T. Choudhury LH. J. Org. Chem.  2008,  73:  8398 
  • 5 Khan AT. Parvin T. Choudhury LH. Eur. J. Org. Chem.  2008,  834 
  • 6 Shen L. Cao S. Liu N. Wu J. Zhu L. Qian X. Synlett  2008,  1341 
  • 7 Kumar A. Maurya RA. Synlett  2008,  883 
  • 8 Ramalingan C. Kwak Y.-W. Tetrahedron  2008,  64:  5023 
  • 9 Noël R. Fargeau-Bellassoued MC. Vanucci-Bacqué C. Lhommet G. Synthesis  2008,  1948 
  • 10 Hulme R. Zamora ODP. Mota EJ. Pastén MA. Contreras-Rojas R. Miranda R. Valencia-Hernández I. Correa-Basurto J. Trujillo-Ferrara J. Delgado F. Tetrahedron  2008,  64:  3372 
  • 11 Khan AT. Choudhury LH. Parvin T. Ali MA. Tetrahedron Lett.  2006,  47:  8137 
  • 12 Khan AT. Parvin T. Choudhury LH. Tetrahedron  2007,  63:  5593