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Article

Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization

by
Aleksejs Burcevs
1,
Armands Sebris
1,
Irina Novosjolova
1,*,
Anatoly Mishnev
2 and
Māris Turks
1,*
1
Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
2
Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, Latvia
*
Authors to whom correspondence should be addressed.
Molecules 2025, 30(2), 337; https://doi.org/10.3390/molecules30020337
Submission received: 21 December 2024 / Revised: 13 January 2025 / Accepted: 13 January 2025 / Published: 16 January 2025
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Abstract

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 indoles; purines; triazole ring-opening; indole synthesis; metal-free approach
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MDPI and ACS Style

Burcevs, A.; Sebris, A.; Novosjolova, I.; Mishnev, A.; Turks, M. Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization. Molecules 2025, 30, 337. https://doi.org/10.3390/molecules30020337

AMA Style

Burcevs A, Sebris A, Novosjolova I, Mishnev A, Turks M. Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization. Molecules. 2025; 30(2):337. https://doi.org/10.3390/molecules30020337

Chicago/Turabian Style

Burcevs, Aleksejs, Armands Sebris, Irina Novosjolova, Anatoly Mishnev, and Māris Turks. 2025. "Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization" Molecules 30, no. 2: 337. https://doi.org/10.3390/molecules30020337

APA Style

Burcevs, A., Sebris, A., Novosjolova, I., Mishnev, A., & Turks, M. (2025). Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization. Molecules, 30(2), 337. https://doi.org/10.3390/molecules30020337

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