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Synthesis 2005(5): 753-756
DOI: 10.1055/s-2005-861785
DOI: 10.1055/s-2005-861785
PAPER
© Georg Thieme Verlag Stuttgart · New YorkFeCl3-Promoted Intramolecular Annulation of δ-Keto Nitriles: Facile Approach to Prepare 3-Acetamido-2-pyridone Derivatives
Further Information
Received
20 October 2004
Publication Date:
18 January 2005 (online)
Publication History
Publication Date:
18 January 2005 (online)
Abstract
A facile approach was developed to synthesize 3-acetamido-2-pyridone derivatives in moderate yields from δ-keto nitriles, derived from Michael addition between ethyl acetamidocyanoacetate and α,β-unsaturated ketones. The tandem reaction sequence promoted by FeCl3 involves intramolecular ketone-nitrile annulation followed by aromatization via selective decarbethoxylation. A plausible mechanism is also described.
Key words
δ-keto nitrile - 3-acetamido-2-pyridone - ferric chloride
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