Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization
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 &l...
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/337 |
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| author | Aleksejs Burcevs Armands Sebris Irina Novosjolova Anatoly Mishnev Māris Turks |
| author_facet | Aleksejs Burcevs Armands Sebris Irina Novosjolova Anatoly Mishnev Māris Turks |
| author_sort | Aleksejs Burcevs |
| collection | DOAJ |
| description | 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 <i>N</i>-aryl ethene-1,1-diamines. In the second step, the latter intermediates are cyclized into the target 1<i>H</i>-indoles in the presence of iodine. The developed method ensures the synthesis of indoles that possess <i>N</i>-substituents at the indole <i>C</i>2 position. Depending on the applied <i>N</i>-nucleophile, the indolization step provides a selectivity either towards 1<i>H</i>-indoles or 1-aryl-1<i>H</i>-indoles. |
| format | Article |
| id | doaj-art-8848375b62d84583bc32a3266fbd163c |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-8848375b62d84583bc32a3266fbd163c2025-01-24T13:43:40ZengMDPI AGMolecules1420-30492025-01-0130233710.3390/molecules30020337Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent CyclizationAleksejs Burcevs0Armands Sebris1Irina Novosjolova2Anatoly Mishnev3Māris Turks4Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, LatviaInstitute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaA 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 <i>N</i>-aryl ethene-1,1-diamines. In the second step, the latter intermediates are cyclized into the target 1<i>H</i>-indoles in the presence of iodine. The developed method ensures the synthesis of indoles that possess <i>N</i>-substituents at the indole <i>C</i>2 position. Depending on the applied <i>N</i>-nucleophile, the indolization step provides a selectivity either towards 1<i>H</i>-indoles or 1-aryl-1<i>H</i>-indoles.https://www.mdpi.com/1420-3049/30/2/337indolespurinestriazole ring-openingindole synthesismetal-free approach |
| spellingShingle | Aleksejs Burcevs Armands Sebris Irina Novosjolova Anatoly Mishnev Māris Turks Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization Molecules indoles purines triazole ring-opening indole synthesis metal-free approach |
| title | Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization |
| title_full | Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization |
| title_fullStr | Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization |
| title_full_unstemmed | Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization |
| title_short | Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization |
| title_sort | synthesis of indole derivatives via aryl triazole ring opening and subsequent cyclization |
| topic | indoles purines triazole ring-opening indole synthesis metal-free approach |
| url | https://www.mdpi.com/1420-3049/30/2/337 |
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