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A copper-mediated oxidative radical addition/cyclization cascade of o-cyanoarylacrylamides with sodium trifluoromethanesulfonate (Langlois’ reagent) has been achieved. The reaction proceeds through radical addition, cyclization, and imine hydrolysis, in which the cyclization was accomplished by an intramolecular addition of the carbon radical to the nitrile. This transformation exhibits a wide substrate scope and good functional group tolerance, thus providing a highly efficient and practical access to a variety of trifluoromethylated quinoline-2,4(1H,3H)-diones. Furthermore, using other sulfinic acid sodium salts as sulfonylating agents, sulfonated quinolinediones were also obtained through a similar radical cascade.

A convenient and efficient iron-catalyzed radical addition/cyclization cascade of o-cyanoarylacrylamides with alcohols is presented for the synthesis of carbonyl substituted quinoline-2,4(1H,3H)-diones in moderate to excellent yields. This transformation exhibits a wide substrate scope and significant functional group tolerance.

Oxidative radical addition/cyclization cascade of o-cyanoarylacrylamides with α-keto acids as well as aldehydes is reported. This transformation exhibits a wide substrate scope and significant functional group tolerance and provides a convenient and highly efficient access to carbonyl-containing quinoline-2,4(1H,3H)-diones. A possible mechanism for the transformation is proposed.

The title compounds are efficiently obtained by radical mediated cascade reaction which shows significant functional group tolerance.

isolation and structural elucidation of steroidal alkaloids veraussine A (Ia) and veraussine B (Ib)