Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives

Nishino H., Kumabe R., Hamada R., YAKUT M.

TETRAHEDRON, cilt.70, sa.7, ss.1437-1450, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 7
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tet.2014.01.013
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1437-1450
  • Anahtar Kelimeler: Hydroperoxides, Endoperoxides, Quinolines, Propellanes, Aerobic oxidation, Mn(III), xidation, OXIDATIVE RADICAL CYCLIZATION, CERIUM(IV) AMMONIUM-NITRATE, MANGANESE(III) ACETATE, 1,3-DICARBONYL COMPOUNDS, FACILE SYNTHESIS, GAMMA-LACTONES, METAL-SALTS, QUINAZOLINE, OLEFINS, 3-OXOPROPANENITRILES
  • Ankara Üniversitesi Adresli: Evet

Özet

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.