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Titolo:
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
Autore:
Uchiyama, K; Ono, A; Hayashi, Y; Narasaka, K;
Indirizzi:
Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo Tokyo Japan 1130033 ept Chem, Bunkyo Ku, Tokyo 1130033, Japan
Titolo Testata:
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
fascicolo: 12, volume: 71, anno: 1998,
pagine: 2945 - 2955
SICI:
0009-2673(199812)71:12<2945:RSOQA1>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
IMINYL RADICALS; BECKMANN REARRANGEMENT; TRIFLUOROMETHANESULFONIC ACID; INTRAMOLECULAR CYCLIZATION; OXIME SULFONATE; DERIVATIVES; TRANSFORMATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
39
Recensione:
Indirizzi per estratti:
Indirizzo: Narasaka, K Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo Tokyo Japan 1130033 nkyo Ku, Tokyo 1130033, Japan
Citazione:
K. Uchiyama et al., "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", B CHEM S J, 71(12), 1998, pp. 2945-2955

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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 18/11/17 alle ore 05:51:12