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FeCl 3 ⋅6H 2 O‐Catalyzed Intermolecular‐Cascade Cyclization of Acetoacetanilide: Aldehyde‐Tuned Synthesis to Valuable 2‐Pyridone Analogues
Author(s) -
Sengupta Tista,
Gayen Krishnanka S.,
Pandit Palash,
Maiti Dilip K.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103354
Subject(s) - chromone , intermolecular force , cascade , chemistry , aldehyde , catalysis , lewis acids and bases , stereochemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , molecule , chromatography
The first ever breakthrough toward activation of β‐ketoacetanilide and subsequent CC and CN 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).