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Note | Regular issue | Vol 60, No. 4, 2003, pp.953-957
Published online, 10th February, 2003
DOI: 10.3987/COM-02-9702
Improved Oxidation of Active Methyl Group of N-Heteroaromatic Compounds by Selenium Dioxide in the Presence of tert-Butyl Hydroperoxide

Yoshinobu Tagawa, Katsuya Yamashita, Yoshitaka Higuchi, and Yoshinobu Goto*

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


The oxidation of active methyl group of N-heteroaromatic compounds including both of bicyclic and monocyclic compounds using SeO2 was considerably improved in the presence of tert-butyl hydroperoxde in dioxane to give the corresponding aldehyde or carboxylic acid in the moderate to good yields. The present oxidation proceeds more mildly and more selectively to form aldehyde rather than carboxylic acid, compared with conventional SeO2 oxidation without tert-butyl hydroperoxide.