Selective Synthesis of 3-(1 H -Tetrazol-5-yl)-indoles from 2 H -Azirines and Arynes.
| Autor: | Grosso C; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal., Alves C; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal., Sase TJ; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal., Alves NG; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal., Cardoso AL; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal., Lemos A; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal.; FCT, University of Algarve, Campus Gambelas, 8005-139 Faro, Portugal., Pinho E Melo TMVD; University of Coimbra, Coimbra Chemistry Center-Institute of Molecular Sciences (CQC-IMS) and Department of Chemistry, 3004-535 Coimbra, Portugal. |
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| Jazyk: | angličtina |
| Zdroj: | ACS omega [ACS Omega] 2024 Jun 24; Vol. 9 (27), pp. 29282-29289. Date of Electronic Publication: 2024 Jun 24 (Print Publication: 2024). |
| DOI: | 10.1021/acsomega.4c00305 |
| Abstrakt: | A new selective synthetic approach to indole derivatives bearing a tetrazole moiety has been developed. Arynes, generated in situ from o -(trimethylsilyl)aryl triflates and KF, reacted smoothly with 2-(2-benzyl-2 H -tetrazol-5-yl)-2 H -azirines to give 3-(2-benzyl-2 H -tetrazol-5-yl)-indole derivatives with high selectivity. Deprotection of the tetrazole moiety gave 3-(1 H -tetrazol-5-yl)-indole derivatives. Competing Interests: The authors declare no competing financial interest. (© 2024 The Authors. Published by American Chemical Society.) |
| Databáze: | MEDLINE |
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