Tetrahedron

Oxidative degradation of 8-nitroquinoline with hydrogen peroxide in acetic acid a possible mechanism through 3, 4-epoxide of quinoline ring

T Kaiya, Y Kawazoe

Index: Kaiya, Toyo; Kawazoe, Yutaka Tetrahedron, 1985 , vol. 41, # 3 p. 511 - 518

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Citation Number: 2

Abstract

The treatment of 8-nitroquinoline with hydrogen peroxide and acetic acid at 60° C afforded 7- nitroindole, 7-nitro-2-oxindole, 2-amino-3-nitrobenzoic acid, 2-amino-3-nitrobenzaldehyde, 3, 4-dihydro-3, 4-trans-dihydroxy-8-nitrocarbostyril, 3, 4-trans-dihydro-3-hydroxy-4-acetoxy-8- nitrocarbostyril, and 1-(2-amino-3-nitrophenyl)-2-hydroxy-ethanone. The reaction mechanism acceptable in elucidating the formation of these products involves, at the initial ...