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Paper | Regular issue | Vol 29, No. 9, 1989, pp.1741-1760
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5040
Nitrosation of 1-Alkylisoquinolines and Their N-Oxides and Configurational Assignments of Their Oximes

Yoshinobu Tagawa, Hiromi Arakawa, and Yoshinobu Goto*

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


Nitrosation of 1-methyl-, 1-ethylisoquinoline and their N-oxides with alkyl nitrite was studied under various conditions, and the following three systems, (t-BuONO and t-BuOK in THF), (t-BuONO and t-BuOK in liq. NH3) and (t-BuONO and n-BuLi-t-BuOK in THF), were found to be generally effective for nitrosation of not only isoquinolines but also pyridine and quinoline derivatives. The δOHCH=N and δOH values were shown to be reliable criterions for assigning configurations of aldoximes and methylketoximes in these series. The semi-empirical molecular orbital calculations (MNDO method) about the reactivity of isoquinoline derivatives and the stability of ketoximes were in good qualitative agreement with the experimental results.