Novel approach to 3,4-dihydro-2(1H)-quinolinone derivatives via cyclopropane ring expansion.
N-(1'-Alkoxy)cyclopropyl-2-haloanilines are transformed to 3,4-dihydro-2((1)H)-quinolinones via palladium-catalyzed cyclopropane ring expansion. The reaction tolerates a variety of functional groups such as ester, nitrile, ether, and ketone groups.
Tsuritani
Takayuki
T
Process Research, PreClinical Department, Banyu Pharmaceutical Co. Ltd., 3 Okubo, Tsukuba, Ibaraki 300-2611, Japan. takayuki_tsuritani@merck.com
Yamamoto
Yuhei
Y
Kawasaki
Masashi
M
Mase
Toshiaki
T
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D003521:Cyclopropanes; D006846:Hydrocarbons, Halogenated; D015363:Quinolones; D010165:Palladium