FeCl3-Mediated synthesis of polysubstituted tetrahydroquinolines via domino Mannich/Friedel–Crafts reactions of aldehydes and amines

Yan-Fang Yang; Xing-Zhong Shu; Hai-Long Wei; Jian-Yi Luo; Shaukat Ali; Xue-Yuan Liu; Yong-Min Liang

doi:10.1039/C1OB05646H

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FeCl₃-Mediated synthesis of polysubstituted tetrahydroquinolines via domino Mannich/Friedel–Crafts reactions of aldehydes and amines†

Yan-Fang Yang,^a Xing-Zhong Shu,^a Hai-Long Wei,^a Jian-Yi Luo,^a Shaukat Ali,^a Xue-Yuan Liu^a and Yong-Min Liang*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, People's Republic of China

^b State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou, People's Republic of China
E-mail: liangym@lzu.edu.cn
Fax: (+86)-931-891-2582

Abstract

A useful method to construct highly substituted tetrahydroquinolines has been developed through an iron(III) chloride-mediated domino Mannich and intramolecular Friedel–Crafts alkylation followed by intermolecular Friedel–Crafts alkylation reactions of aliphatic aldehydes with aromatic amines.

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Article information

DOI: https://doi.org/10.1039/C1OB05646H
Article type: Communication
Submitted: 25 Apr 2011
Accepted: 17 May 2011
First published: 17 May 2011

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Org. Biomol. Chem., 2011,9, 5028-5033

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FeCl₃-Mediated synthesis of polysubstituted tetrahydroquinolines via domino Mannich/Friedel–Crafts reactions of aldehydes and amines

Y. Yang, X. Shu, H. Wei, J. Luo, S. Ali, X. Liu and Y. Liang, Org. Biomol. Chem., 2011, 9, 5028 DOI: 10.1039/C1OB05646H

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Organic & Biomolecular Chemistry