- 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
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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.
- Uchiyama, Katsuya
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p. 2945 - 2955
(2007/10/03)
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- Synthesis of 8-hydroxyquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes
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8-Hydroxyquinolines are synthesized from O-2,4-dinitrophenyloximes of m-hydroxyphenethyl ketones by the treatment with sodium hydride, and then with 2,3-dichloro4,5-dicyano-p-benzoquinone (DDQ).
- Uchiyama, Katsuya,Hayashi, Yujiro,Narasaka, Koichi
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p. 445 - 446
(2007/10/03)
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