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

Synthesis DOI: 10.1055/s-0039-1690681 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. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - September 12, 2019 Category: Chemistry Authors: Szewczyk, Milena Ryczkowska, Ma łgorzata Makowiec, S ławomir Tags: paper Source Type: research