Synthesis of Quinoline-2-thiones by Selective Deoxygenative C<i>–</i>H/C<i>–</i>S Functionalization of Quinoline <i>N</i>-Oxides with Thiourea

Abstract

Quinoline-2-thiones valuable for synthetic and medicinal chemistry applications were obtained with excellent regioselectivity employing a deoxygenative C–H functionalization of readily available quinoline- N -oxides with thiourea upon activation with triflic anhydride. Unlike the current methods, this approach provides general access to diverse quinoline-2-thiones functionalized with groups of different electronic natures. Experimental simplicity and good to high yields are advantages of this protocol. Given the high reactivity of quinoline-2-thiones, this method provides an entry point for the synthesis of diverse organosulfur quinoline scaffolds.

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