期刊
TETRAHEDRON
卷 70, 期 7, 页码 1437-1450出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.01.013
关键词
Hydroperoxides; Endoperoxides; Quinolines; Propellanes; Aerobic oxidation; Mn(III); xidation
资金
- Japan Society for the Promotion of Science [22550041, 25410049]
- Grants-in-Aid for Scientific Research [25410049, 22550041] Funding Source: KAKEN
The reactions of 1,1-disubstituted alkenes with 4-hydroxyquinolin-2(1H)-ones under both Mn(III)-catalyzed aerobic oxidation conditions at room temperature and Mn(III)-mediated oxidation conditions at reflux temperature are described. The Mn(III)-catalyzed aerobic oxidation afforded bis(hydroperoxyethyl)quinolinones and azatrioxa[4.431propellanes, while the oxidation with Mn(OAc)(3)center dot 2H(2)O produced furo[3,2-c]quinolin-4-one analogues. The existence of a substituent at the 3-position of the 4-hydroxyquinolin-2(1H)-ones prevented a double reaction with the alkenes, and (endoperoxy)quinolinones and/or (hydroperoxyethyl)quinolinones were obtained under the Mn(III)-catalyzed aerobic conditions, while furo[3,2-c]quinolinone hemiacetals and vinylquinolinones were selectively produced under the Mn(III)-mediated oxidation conditions depending on the reaction temperature and times. Cyclic assembly of quinolinone-related 1,3-dicarbonyl compounds such as dihydropyridinones, pyranones, and dimedone derivatives was also examined under elevated temperature conditions. (C) 2014 Elsevier Ltd. All rights reserved.
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