Synthesis of 2,3-dihydroquinolin-4(1H)-ones through catalytic metathesis of o-alkynylanilines and aldehydes.
SbF5-MeOH catalytic system efficiently promotes the alkyne-carbonyl metathesis of o-alkynylaniline derivatives and aldehydes to afford 2,3-disubstituted dihydroquinolinones in moderate to high yields with high trans-selectivity.
Saito
Akio
A
Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan. akio-sai@ac.shoyaku.ac.jp
Kasai
Jun
J
Odaira
Yu
Y
Fukaya
Haruhiko
H
Hanzawa
Yuji
Y
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D000965:Antimony / Q000737:chemistry*; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C545227:2,3-dihydroquinolin-4(1H)-one; D000447:Aldehydes; D000480:Alkynes; D000814:Aniline Compounds; D015363:Quinolones; C529140:antimony pentafluoride; D000965:Antimony; D005459:Fluorides; D000432:Methanol