Synthesis and thermolysis of 3-azidoindolenines.

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Several new 3-azidoindolenines have been synthesized in high yields (i) by the reaction of 2, 3-disubstituted indoles with iodine azide or bromine azide, and (ii) by the reaction of 3-chloroindolenines with sodium azide in acetic acid. The 3-azidoindolenines undergo thermal rearrangement in variable yields and ratios to quinoxalines and quinazolines, along with the formation of the parent indoles. The ring-expansion of 3-azido-2, 3-diphenylindolenine to 2, 3-diphenylquinoxaline also occurs on treatment with acid but in much lower yield. Photolysis of the 3-azidoindolenines gives the parent indoles as major products.

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