Concerning model metabolites of the carcinogen 4-nitroquinoline 1-oxide. Reactivity and solvolytic behavior of 1-hydroxy-4-(acetoxyimino)-1, 4-dihydroquinoline
M Demeunynck, MF Lhomme, JM Mellor…
文献索引：Demeunynck, Martine; Lhomme, Marie-France; Mellor, John M.; Lhomme, Jean Journal of Organic Chemistry, 1989 , vol. 54, # 2 p. 399 - 405
l-Hydroxy-4-(acetoxyimino)-1, 4-dihydroquinoline is obtained quantitatively by reaction of l- acetoxy-4-(acetoxyimino)-1, 4-dihydroquinoline with piperidine in dimethyl sulfoxide. Spectroscopic results establish that this monoacetate exists preferentially as a hydroxylamine tautomer rather than as an N-oxide in the pH range 2-9, but below pH 2 protonation affords the N-protonated ester and above pH 9 an anion is formed. Hydrolysis ...
