Chemistry: A European Journal 2012-02-13

FeCl3⋅6H2O-catalyzed intermolecular-cascade cyclization of acetoacetanilide: aldehyde-tuned synthesis to valuable 2-pyridone analogues.

Tista Sengupta, Krishnanka S Gayen, Palash Pandit, Dilip K Maiti

Index: Chemistry 18(7) , 1905-9, (2012)

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Abstract

The first ever breakthrough toward activation of β-ketoacetanilide and subsequent C-C and C-N bond-forming intermolecular-cascade cyclization processes is demonstrated by development of the unprecedented Lewis acid property of non-toxic FeCl(3)⋅6H(2)O. 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).Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.