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Paper | Regular issue | Vol 68, No. 12, 2006, pp.2563-2570
Published online, 27th October, 2006
DOI: 10.3987/COM-06-10881
Electrooxidative Cyclization of Hydroquinolyl Alcohols

Mitsuhiro Okimoto,* Takashi Yoshida, Masayuki Hoshi, Kazuyuki Hattori, Masashi Komata, Kaori Numata, and Kenta Tomozawa

*Department of Applied and Environmental Chemistry, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan


Several hydroquinolyl, hydroisoquinolyl, and indolinyl alcohols were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide. The hydroquinolyl and hydroisoquinolyl alcohols afforded the corresponding intramolecular cyclization products through the bond formation between the α-carbon of the nitrogen atom and the oxygen atom of the hydroxy group. In contrast, the indolinyl alcohols underwent dehydrogenation to give the corresponding indolyl alcohols. Presumably, in all cases, the electrooxidation involves a two-electron oxidation process.