title: FeCl3⋅6H2O-catalyzed intermolecular-cascade cyclization of acetoacetanilide: aldehyde-tuned synthesis to valuable 2-pyridone analogues.
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).
authors.affiliation: Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata-700009, India.
authors.forename: Tista
authors.initials: T
authors.lastname: Sengupta
authors.forename: Krishnanka S
authors.initials: KS
authors.lastname: Gayen
authors.forename: Palash
authors.initials: P
authors.lastname: Pandit
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Maiti
mesh_terms: D000083:Acetanilides / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000083:Acetanilides; D000447:Aldehydes; D002712:Chlorides; D005290:Ferric Compounds; D011728:Pyridones; C017679:2-hydroxypyridine; C024555:ferric chloride; C056965:acetoacetanilide