Synthesis of 2,4-Dicyanoalkylated Benzoxazines through the Radical-Mediated Cascade Cyclization of Isocyanides with AIBN under Metal- and Additive-Free Conditions

A general and novel method for the radical cascade cyclization of aryl isocyanides with AIBN has been described. This strategy provides straightforward access to various 2,4-dicyanoalkylated benzoxazines in moderate to good yields under metal- and additive-free conditions. The reaction can apply to a gram scale and tolerate diverse functional groups. 2,4-Dicyanoalkylated benzoxazine derivatives feature a large Stokes shift and intramolecular charge transfer properties.