Abstract
Flash vacuum pyrolysis of N-(2-nitroheteroaryl)indoles or -carbazoles at 875 ˚C gave aza analogues of strained pyrrolo[3,2,1-jk]carbazole (50-55%) and indolo[3,2,1-jk]carbazole (55-85%) ring systems, respectively, through generation of aryl radicals and cyclization. The corresponding reactions of N-(2-nitroheteroaryl)indazoles and -benzimidazoles at 850 ˚C, on the other hand, gave carbazole-1-carbonitrile derivatives (56-64%) by a mechanism involving radical ring opening and hydrogen atom rearrangement.
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