Access to 2-thio/selenoquinolines via domino reaction of isocyanides with sulfur and selenium in water
Literature Information
Haitao Liu, Mengying Jia, Shaoguang Sun, Xianxiu Xu
A domino reaction of o-alkenylaryl isocyanides with elemental sulfur and selenium in pure water was developed for the efficient and green synthesis of quinoline-2-thione and diquinolyl diselenide derivatives. Mechanistical investigation reveals that intramolecular nucleophilic addition of an alkenyl group to the in situ generated isothio/isoselenocyanate accounts for the formation of a quinoline-ring. Moreover, this transformation is also amendable for the convenient preparation of 2-fluoromethylthio-/seleno-quinolines by a one-pot three-component reaction.
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