Unique tandem Heck-lactamization naphthyridinone ring formation between acrylanilides and halogenated pyridines.
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.
Cvetovich
Raymond J
RJ
Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. raymond_cvetovich@merck.com
Reamer
Robert A
RA
DiMichele
Lisa
L
Chung
John Y L
JY
Chilenski
Jennifer R
JR
D000813:Anilides / Q000737:chemistry*; D003500:Cyclization; D006219:Halogens / Q000737:chemistry* / Q000378:metabolism; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry* / Q000378:metabolism
D000813:Anilides; D006219:Halogens; D007769:Lactams; D009287:Naphthyridines; D011725:Pyridines; D010165:Palladium