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

Grosso, Carla; Alves, Cláudia; Sase, Terver J.; Alves, Nuno G.; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho e; Lemos, Americo

http://hdl.handle.net/10400.1/25686

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Autores

Melo, Teresa M. V. D. Pinho e

Lemos, Americo

Resumo(s)

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.