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Paper | Special issue | Vol 64, No. 1, 2004, pp.193-198
Published online, 29th June, 2004
DOI: 10.3987/COM-04-S(P)11
Novel Synthesis of Benzoxazoles from o-Nitrophenols and Amines

Hiromi Nishioka,* Yukiko Ohmori, Yumiko Iba, Eri Tsuda, Takashi Hrayama*

*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

o-Nitrophenols and o-nitroaniline were reacted with amines at 210-215°C to produce the corresponding benzoxazoles and benzimidazoles, respectively, in moderate yields. The reactions between o-nitrophenols containing a CO2Me or OMe group on their benzene rings and N,N-diethylaniline were examined to investigate the effects of the position and electronic character of these substituents on the formation of the oxazole ring.