4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings

Shaomin Chen; Palanisamy Ravichandiran; Ahmed El-Harairy; Yves Queneau; Minghao Li; Yanlong Gu

doi:10.1039/C9OB01045A

4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings†

Shaomin Chen,^a Palanisamy Ravichandiran,^a Ahmed El-Harairy,^a Yves Queneau,

^b Minghao Li^a and Yanlong Gu

*^ac

Author affiliations

* Corresponding authors

^a Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China
E-mail: klgyl@hust.edu.cn

^b Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Univ Lyon, CNRS, Université Lyon 1, INSA Lyon, CPE Lyon, ICBMS, UMR 5246, Université Claude Bernard, Bâtiment Lederer, 1 Rue Victor Grignard, 69622 Villeurbanne Cedex, France

^c State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou, China

Abstract

A straightforward access to tricyclic indoles bearing 3,4-fused seven-membered rings has been established by using 4-aminoindoles as 1,4-bisnucleophiles in three-component reactions. 1H-Azepino[4,3,2-cd]indoles, 4,6-dihydro-1H-azepino[4,3,2-cd]indoles and 1,3,4,6-tetrahydro-5H-azepino[4,3,2-cd]indol-5-ones could thus be synthesized in one pot in moderate to good yields. Beyond opening access to 3,4-fused tricyclic indoles, the use of easily accessible 4-aminoindoles as C,N-1,4-bisnucleophiles also provides a new platform to be used in a diversity-oriented synthesis strategy, fully displaying its benefits of maximizing molecular complexity and reaction diversity.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01045A
Article type: Paper
Submitted: 07 May 2019
Accepted: 28 May 2019
First published: 30 May 2019

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Org. Biomol. Chem., 2019,17, 5982-5989

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4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings

S. Chen, P. Ravichandiran, A. El-Harairy, Y. Queneau, M. Li and Y. Gu, Org. Biomol. Chem., 2019, 17, 5982 DOI: 10.1039/C9OB01045A

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Organic & Biomolecular Chemistry

4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings†

Abstract

Supplementary files

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4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings

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