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Paper | Special issue | Vol 97, No. 2, 2018, pp.842-853
Published online, 26th April, 2018
DOI: 10.3987/COM-18-S(T)60
Metal-Free Synthesis of N-Containing Heterocycles from o-Substituted Aniline Derivatives via 2,4,6-Trihydroxybenzoic Acid-Catalyzed Oxidative Dehydrogenation of Benzylamines under Oxygen Atmosphere

Shun Kumazawa, Akinori Uematsu, Chun-ping Dong, Shintaro Kodama, Akihiro Nomoto, Michio Ueshima, and Akiya Ogawa*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuencho, Sakai, Osaka 593-8531, Japan


A series of N-heterocycles, i.e., benzimidazoles, benzoxazoles, and benzothiazoles, can be conveniently synthesized by the oxidative cyclization of benzylamines with o-substituted aniline derivatives, i.e., o-phenylenediamines, o-aminophenols, and o-aminothiophenols, using 2,4,6-trihydroxybenzoic acid as an organocatalyst under an oxygen atmosphere. This approach provides a mild and efficient tool towards benzimidazoles and benzothiazoles with good yields and a broad substrate scope. The developed synthesis of N-heterocycles might proceed via the oxidative dehydrogenation of benzylamines (ArCH2NH2), generating the corresponding imines (ArCH=NH) as key intermediates.