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.
Authors
Additional information
- DOI
- Digital Object Identifier link open in new tab 10.1055/s-0039-1690681
- Category
- Publikacja w czasopiśmie
- Type
- artykuły w czasopismach
- Language
- angielski
- Publication year
- 2019