Site-selective C5-H and N-H alkylation of unprotected 8-aminoquinolines

8-Aminoquinolines are the building blocks of many pharmaceutical compounds, which has motivated the scientific community to develop new ways to derivatize these compounds. In this work, we performed a site-selective C5-H and N-H alkylation of 8-aminoquinolines using para-quinone methides under extremely mild conditions. C5-H alkylation was performed using protecting group-free 8-aminoquinolines and in metal-free conditions. N-H alkylations were also carried out under mild conditions. All corresponding alkylation products were obtained in high to excellent yields.