Direct thioalkylation of nitroquinolines with alkanethiolate anions via nucleophilic displacement of a ring hydrogen atom

Abstract

Nitroquinolines readily react with alkanethiols in tetrahydrofuran in the presence of excess sodium hydride to give the corresponding alkylthio derivatives via the preferential displacement of a ring hydrogen atom adjacent to the nitro group. After an induction period, the reaction starts and completes within a short time even at low temperature, suggesting the involvement of a radical species as an intermediate. Using this methodology, a series of thioalkylation products have been prepared from 5-, 6-, 7- and 8-nitroquinolines in good to moderate yields.