Metal-free nitro/azido cyclization of 1-acryloyl-2-cyanoindoles to access NO 2 /N 3 -featuring pyrrolo[1,2- a ] indolediones.

An H 2 O/heating or [bis(trifluoroacetoxy)iodo]benzene promoted radical cascade nitro/azide cyclization of 1-acryloyl-2-cyanoindoles with tert -butyl nitrite/azidotrimethylsilane was accomplished, which offered a series of nitro/azide-featuring pyrrolo[1,2- a ]indolediones in good yields. Meanwhile, some scale-up experiments and substituent transformations were performed to test the synthetic value. In addition, the corresponding radical intermediates were successfully detected by HRMS to support the possible reaction pathway.