Regioselective Synthesis of Quinolin-8-ols and 1, 2, 3, 4-Tetrahydroquinolin-8-ols by the Cyclization of 2-(3-Hydroxyphenyl) ethyl Ketone 0-2, 4-Dinitrophenyloximes.
K Uchiyama, A Ono, Y Hayashi…
Index: Uchiyama, Katsuya Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 12 p. 2945 - 2955
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Citation Number: 30
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 [BH 3 (CN)] affords 1, 2, 3, 4-tetrahydroquinolin-8-ols. The present cyclization proceeds via alkylideneaminyl radical intermediates generated by the single ...
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