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Selective Synthesis of 3‑(1H‑Tetrazol-5-yl)-indoles from 2H‑Azirines and Arynes

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journal contribution
posted on 2024-06-24, 23:43 authored by Carla Grosso, Cláudia Alves, Terver J. Sase, Nuno G. Alves, Ana L. Cardoso, Américo Lemos, Teresa M. V. D. Pinho e Melo
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-2H-tetrazol-5-yl)-2H-azirines to give 3-(2-benzyl-2H-tetrazol-5-yl)-indole derivatives with high selectivity. Deprotection of the tetrazole moiety gave 3-(1H-tetrazol-5-yl)-indole derivatives.

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