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

Milena Witkowska; Małgorzata Ryczkowska; Sławomir Makowiec

doi:10.1055/s-0039-1690681

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.

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Publication version: Accepted or Published Version
License: Copyright (2019 Georg Thieme Verlag Stuttgart)

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Category:: Articles
Type:: artykuły w czasopismach
Published in:: SYNTHESIS-STUTTGART no. 51, pages 4625 - 4634,
ISSN: 0039-7881
Language:: English
Publication year:: 2019
Bibliographic description:: Witkowska M., Ryczkowska M., Makowiec S.: Transition-Metal-Promoted Oxidative Cyclization To Give 1,2,4-Trisubstituted Carbazole Scaffolds// SYNTHESIS-STUTTGART -Vol. 51,iss. 24 (2019), s.4625-4634
DOI:: Digital Object Identifier (open in new tab) 10.1055/s-0039-1690681
Verified by:: Gdańsk University of Technology