FeCl3⋅6H2O-Catalyzed Intermolecular-Cascade Cyclization of Acetoacetanilide: Aldehyde-Tuned Synthesis to Valuable 2-Pyridone Analogues

Authors

  • Tista Sengupta,

    1. Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009 (India), Fax: (+91) 33-2351-9755
    Search for more papers by this author
  • Krishnanka S. Gayen,

    1. Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009 (India), Fax: (+91) 33-2351-9755
    Search for more papers by this author
  • Dr. Palash Pandit,

    1. Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009 (India), Fax: (+91) 33-2351-9755
    Search for more papers by this author
  • Dr. Dilip K. Maiti

    Corresponding author
    1. Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009 (India), Fax: (+91) 33-2351-9755
    • Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009 (India), Fax: (+91) 33-2351-9755
    Search for more papers by this author

Abstract

original image

The first ever breakthrough toward activation of β-ketoacetanilide and subsequent C[BOND]C and C[BOND]N bond-forming intermolecular-cascade cyclization processes is demonstrated by development of the unprecedented Lewis acid property of non-toxic FeCl36H2O. Aromatic, aliphatic, α,β-unsaturated, chiral sugar-based and chromone aldehydes were regio- and stereoselectively cyclized with acetoacetanilides toward construction of valuable N-containing highly functionalized 2-pyridones (see scheme for an example).

Ancillary