Tetrahedron

Kinetics and mechanism of the base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinolines in DMSO/H 2 O

M Czaun, G Speier, J Kaizer, N El Bakkali-Taheri…

Index: Czaun, Miklos; Speier, Gabor; Kaizer, Jozsef; El Bakkali-Taheri, Nadia; Farkas, Etelka Tetrahedron, 2013 , vol. 69, # 32 p. 6666 - 6672

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Citation Number: 5

Abstract

The oxygenation of 4′-substituted 1H-2-phenyl-3-hydroxy-4-oxoquinolines (PhquinH2) in a DMSO/H2O (50/50) solution leads to the cleavage products at the C2–C3 bond in about 75% yield at room temperature. The oxygenation, deduced from the product compositions, has two main pathways, one proceeding via an endoperoxide leading to CO-release, and the other through a 1, 2-dioxetane intermediate without CO-loss. The reaction is specific ...