Bulletin of the Chemical Society of Japan p. 2945 - 2955 (1998)
Update date:2022-07-30
Topics:
Uchiyama, Katsuya
Cyclization of 2-(3-hydroxyphenyl)ethyl ketone 0-2,4- 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.
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