Oxidative aromatic C–N bond formation: convenient synthesis of N-amino-3-nitrile-indolesviaFeBr3-mediated intramolecular cyclization

Zisheng Zheng; Lina Tang; Yanfeng Fan; Xiuxiang Qi; Yunfei Du; Daisy Zhang-Negrerie

doi:10.1039/C1OB05069A

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Oxidative aromatic C–N bond formation: convenient synthesis of N-amino-3-nitrile-indolesviaFeBr₃-mediated intramolecular cyclization†

Zisheng Zheng,^a Lina Tang,^a Yanfeng Fan,^a Xiuxiang Qi,^a Yunfei Du*^a and Daisy Zhang-Negrerie*^a

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* Corresponding authors

^a Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China
E-mail: duyunfeier@tju.edu.cn, daisy_negrerie@tju.edu.cn
Fax: +86-22-27404031
Tel: +86-22-27404031

Abstract

A variety of functionalized N-amino-3-nitrile-indole derivatives are obtained via an intramolecular hetero-cyclization of 2-aryl-3-substituted hydrazono-alkylnitriles using FeBr₃ as a single electron oxidant. This approach allows the N-moiety on the side-chain to be annulated to the benzene ring during the final synthetic step via direct oxidative aromatic C–N bond formation.

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Article information

DOI: https://doi.org/10.1039/C1OB05069A
Article type: Paper
Submitted: 13 Jan 2011
Accepted: 02 Mar 2011
First published: 02 Mar 2011

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Org. Biomol. Chem., 2011,9, 3714-3725

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Oxidative aromatic C–N bond formation: convenient synthesis of N-amino-3-nitrile-indolesviaFeBr₃-mediated intramolecular cyclization

Z. Zheng, L. Tang, Y. Fan, X. Qi, Y. Du and D. Zhang-Negrerie, Org. Biomol. Chem., 2011, 9, 3714 DOI: 10.1039/C1OB05069A

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Organic & Biomolecular Chemistry