Approach to Polysubstituted 4‑Pyridones from N‑Aryl Acetoacetamides via a N to C 1,3-Acyl Migration Mediated by Sodium Persulfate

• Published in: Journal of organic chemistry Vol. 77; no. 17; pp. 7665 - 7670
• Main Authors: Zhang, Zhiguo, Fang, Shiliang, Liu, Qingfeng, Zhang, Guisheng
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.09.2012; Amer Chemical Soc
• Subjects: Acetamides - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Pyridones - chemical synthesis; Pyridones - chemistry; Science & Technology; Sodium Compounds - chemistry; Sulfates - chemistry; DIKETENE; ACID; DIMERIZATION; AGENTS; INHIBITORS; CATALYST; FACILE; DERIVATIVES; AMIDES; Chemical rearrangement; Pyridone derivatives; Molecular structure; Self condensation; Benzylic compound; Nitrogen heterocycle; Sodium Peroxodisulfates; Aromatic compound; Chemical synthesis; Ketone; X ray diffraction; Pyridine derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo3010217

Mediated by sodium persulfate (Na2S2O8), 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.