Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization
Molecules 2025
Aleksejs Burcevs, Armands Sebris, Irina Novosjolova, Anatolijs Mišņovs, Māris Turks

A metal-free two-step synthetic approach for obtaining indole derivatives from aryl triazole fragment-containing compounds has been developed. In the first step, the Dimroth equilibrium, followed by nitrogen extrusion, Wolff rearrangement, and amine nucleophile addition, leads to the formation of N-aryl ethene-1,1-diamines. In the second step, the latter intermediates are cyclized into the target 1H-indoles in the presence of iodine. The developed method ensures the synthesis of indoles that possess N-substituents at the indole C2 position. Depending on the applied N-nucleophile, the indolization step provides a selectivity either towards 1H-indoles or 1-aryl-1H-indoles.


Keywords
indoles, purines, triazole ring-opening, indole synthesis, metal-free approach
DOI
10.3390/molecules30020337
Hyperlink
https://www.mdpi.com/1420-3049/30/2/337

Burcevs, A., Sebris, A., Novosjolova, I., Mišņovs, A., Turks, M. Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization. Molecules, 2025, Vol. 30, No. 2, Article number 337. e-ISSN 1420-3049. Pieejams: doi:10.3390/molecules30020337

Publication language
English (en)
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