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Communication | Special issue | Vol 17, No. 1, 1982, pp.73-76
Published online, 1st January, 1970
DOI: 10.3987/S-1982-01-0073
Site-selective Effect of N -Oxide Function to Methyl Groups on Six-membered N -Heteroaromatics

Takao Sakamoto, Hiroshi Yoshizawa, Hiroshi Yamanaka,* Yoshinobu Goto, Tokihiro Niiya, and Noriko Honjo

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


Reaction of 2,4-dimethylpyridine 1-oxide with ethyl benzoate under basic conditions afforded 4-methyl-2-phenacylpyridine 1-oxide, while the same reaction of 2,4-dimethylpyridine itself is known to afford 2-methyl-4-phenacylpyridine. Concerning the above contrast, the effect of N-oxide function to the relative reactivity of the 2- and 4-methyl group was investigated on pyridine, quinoline, pyrimidine, and quinazoline homologues. The higher reactivity of α-methyl groups was concluded to be general in the N-oxides of these N-heteroaromatics.