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Paper | Regular issue | Vol 29, No. 9, 1989, pp.1781-1796
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5047
Amination and Nitrosation of Quinolines and Their N-Oxides

Yoshinobu Tagawa, Toshio Yoshida, Noriko Honjo, and Yoshinobu Goto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nakamura, Jonan-ku, Fukuoka, 814-0180, Japan

Abstract

4-Ethylquinoline 1-oxide reacted with isopropyl nitrite and sodium amide in liquid ammonia to give 2-amino-4-ethylquinoline 1-oxide as the main product. Similar amination occurred also with lepidine 1-oxide and quinoline 1-oxide, but only the corresponding oximes were formed from reactions of 4-ethylquinoline and lepidine under the same conditions. Isopropyl nitrite was shown to be most potent as oxidant compared with other oxidants used in such amination. The difference of reactivity between quinoline 1-oxides and quinolines was explained in terms of δδHBF and LUMO energies, calculated by semi-empirical molecular orbital calculation (MNDO method).