Synthesis of 2-Halogenated Quinolines by Halide-Mediated Intramolecular Cyclization of o-Alkynylaryl Isocyanides

Synthesis of 2-Halogenated Quinolines by Halide-Mediated Intramolecular Cyclization of o-Alkynylaryl Isocyanides

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 bromin...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 2010-07, Vol.83 (7), p.822-824
Hauptverfasser: Mitamura, Takenori, Nomoto, Akihiro, Sonoda, Motohiro, Ogawa, Akiya
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container_issue 7
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container_title Bulletin of the Chemical Society of Japan
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creator Mitamura, Takenori
Nomoto, Akihiro
Sonoda, Motohiro
Ogawa, Akiya
description 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 iodide (ion) sources.
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title Synthesis of 2-Halogenated Quinolines by Halide-Mediated Intramolecular Cyclization of o-Alkynylaryl Isocyanides
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