Journal of the Chemical Society. Perkin transactions I p. 2105 - 2111 (1980)
Update date:2022-07-30
Topics:
Kano, Shinzo
Ebata, Tsutomu
Shibuya, Shiroshi
A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furo<3,2-c>quinoline systems (38) and (40), respectively, by application of this method.
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Doi:10.1021/cr60248a004
(1967)Doi:10.1002/cber.19801131107
(1980)Doi:10.1021/ja01352a032
(1931)Doi:10.1016/S0040-4039(00)85812-8
(1982)Doi:10.1039/P29800000255
(1980)Doi:10.1039/jr9350001637
(1935)
