Unique Tandem Heck-Lactamization Naphthyridinone Ring Formation between Acrylanilides and Halogenated Pyridines

• Published in: Journal of organic chemistry Vol. 71; no. 22; pp. 8610 - 8613
• Main Authors: Cvetovich, Raymond J, Reamer, Robert A, DiMichele, Lisa, Chung, John Y. L, Chilenski, Jennifer R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 27.10.2006; Amer Chemical Soc
• Subjects: Anilides - chemistry; Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; Halogens - chemistry; Halogens - metabolism; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Lactams - chemistry; Molecular Structure; Naphthyridines - chemistry; Organic chemistry; Palladium - chemistry; Physical Sciences; Preparations and properties; Pyridines - chemistry; Pyridines - metabolism; Science & Technology; QUINOLINONES; INHIBITORS; Nitrogen heterocycle; Heck reaction; Transition metal; Organic bromine compounds; Palladium; Tandem reaction; Organic chlorine compounds; Organic halogen compounds; Pyridine derivatives; Organic iodine compounds; Aromatic compound; Naphtyridine derivatives; Platinoid
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0613479

The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem Heck-lactamization ring formation to generate 5-chloro-1-aryl-1,6-naphthyridin-2(1H)-ones.