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  • Approach to polysubstituted 4-pyridones from N-aryl acetoacetamides via a N to C 1,3-acyl migration mediated by sodium persulfate.

Approach to polysubstituted 4-pyridones from N-aryl acetoacetamides via a N to C 1,3-acyl migration mediated by sodium persulfate.

The Journal of organic chemistry (2012-08-02)
Zhiguo Zhang, Shiliang Fang, Qingfeng Liu, Guisheng Zhang
ABSTRACT

Mediated by sodium persulfate (Na(2)S(2)O(8)), a series of polysubstituted 4-pyridones were synthesized via self-condensation of N-aryl acetoacetamides, during which a novel N to C 1,3-acyl migration should be involved. The structure of 4-pyridone was unequivocally confirmed by X-ray diffraction analysis. However, the self-condensation of N-benzyl acetoacetamides under the same condition gave polysubstituted 2-pyridones instead of 4-pyridones.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium persulfate, BioXtra, ≥99%
Sigma-Aldrich
Sodium persulfate, BioUltra, ≥99%
Sigma-Aldrich
Sodium persulfate, purum p.a., ≥98% (RT)
Sigma-Aldrich
Sodium persulfate, reagent grade, ≥98%