Synthesis of 2-halogenated quinolines by halide-mediated intramolecular cyclization of o-alkynylaryl isocyanides

T Mitamura, A Nomoto, M Sonoda…

Index: Mitamura, Takenori; Nomoto, Akihiro; Sonoda, Motohiro; Ogawa, Akiya Bulletin of the Chemical Society of Japan, 2010 , vol. 83, # 7 p. 822 - 824

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Citation Number: 10

Abstract

When o-alkynylaryl isocyanides 1 are treated with triethylamine in chloroform, intramolecular chlorinating cyclization of the isocyanides takes place, affording the corresponding 2- chlorinated quinoline derivatives 2 in good to excellent yields, selectively. Bromoform can be also used for the brominating cyclization of 1. Furthermore, fluorinating and iodinating cyclization of o-alkynylaryl isocyanides has been attained by the selection of fluoride and ...