Regioselective Synthesis of Quinolin-8-ols and 1,2,3,4-Tetrahydroquinolin-8-ols by the Cyclization of 2-(3-Hydroxyphenyl)ethyl Ketone O-2,4-Dinitrophenyloximes

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Abstract
Cyclization of 2-(3-hydroxyphenyl)ethyl ketone O-2,4-dinitrophenyloximes proceeds on the oxime nitrogen atom by the treatment with NaH and then with 2,3-dichloro-5,6-dicyano-p-benzoquinone and acetic acid to yield quinolin-8-ols regioselectively. The reaction in the presence of Na[BH3(CN)] affords 1,2,3,4-tetrahydroquinolin-8-ols. The present cyclization proceeds via alkylideneaminyl radical intermediates generated by the single electron transfer between 3-hydroxyphenyl and 2,4-dinitrophenyl moieties.