Transition-Metal-Promoted Oxidative Cyclization To Give 1,2,4-Trisubstituted Carbazole Scaffolds

Abstract

Herein, we describe the synthesis of a 1,2,4-trisubstituted carbazole core from 5-(1H-indol-3-yl)-3-oxopentanoic acid esters or amides. For oxidative cyclization, we tested two different approaches. First, we used manganese triacetate as a conventional moderate oxidizer to ensure the radical course of the reaction. Second, we examined the use of a more complex oxidizing agent I₂/Me(OTf)₃. In both cases, formation of a fused-ring carbazole system with a 2-hydroxyl and 1-carboxylic substituent were observed. In connection with the formation of an unexpected reaction intermediate, mechanistic aspects of the process were discussed.

Key words

carbazole - oxidative cyclization - indole - 3-oxoester - transition metals

• References

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