FeCl3-Promoted Intramolecular Annulation of δ-Keto Nitriles: Facile Approach to Prepare 3-Acetamido-2-pyridone Derivatives

Shaozhong Wang; Jia Pan; Yuefei Hu; Hongwen Hu

doi:10.1055/s-2005-861785

PAPER

FeCl₃-Promoted Intramolecular Annulation of δ-Keto Nitriles: Facile Approach to Prepare 3-Acetamido-2-pyridone Derivatives

Shaozhong Wang*^a, Jia Pan^a, Yuefei Hu^b, Hongwen Hu^a
^a Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
Fax: +86(25)83317761; e-Mail: wangsz@nju.edu.cn;
^b Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China

Abstract

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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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