Synthesis of Mannich-type derivatives from amides activated by hydrogen bonding with ZnCl2

Zhiyu Hu; Zongbo Xie; Zhiqiang Zhu; Bozhen Gong; Guofang Jiang; Zhanggao Le

doi:10.1039/D0OB01989E

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Synthesis of Mannich-type derivatives from amides activated by hydrogen bonding with ZnCl₂†

Zhiyu Hu,^ab Zongbo Xie,

*^ab Zhiqiang Zhu,^ab Bozhen Gong,^ab Guofang Jiang^ab and Zhanggao Le*^ab

Author affiliations

* Corresponding authors

^a Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013, Jiangxi, China
E-mail: zbxie@ecut.edu.cn, zhgle@ecut.edu.cn

^b School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, Jiangxi, China
E-mail: zbxie@ecut.edu.cn, zhgle@ecut.edu.cn

Abstract

The amide group has one of the most significant functionalities found in many natural products. Herein, low-nucleophilic amides are used in a Mannich-type reaction to synthesize N-acyl-protected amine derivatives. A highly efficient synthetic method utilizing simple aldehydes, N-substituted anilines, and amides as substrates was established through a one-pot amide pathway activated by hydrogen bonding between the ZnCl₂ and amide under solvent-free conditions. This strategy can be broadly applied to medicinal chemistry. More importantly, compared with the previous Lewis acid catalyzed reaction, we proposed a new application of zinc chloride.

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

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Article information

DOI: https://doi.org/10.1039/D0OB01989E
Article type: Paper
Submitted: 29 Sep 2020
Accepted: 27 Oct 2020
First published: 27 Oct 2020

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Org. Biomol. Chem., 2020,18, 9095-9099

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Synthesis of Mannich-type derivatives from amides activated by hydrogen bonding with ZnCl₂

Z. Hu, Z. Xie, Z. Zhu, B. Gong, G. Jiang and Z. Le, Org. Biomol. Chem., 2020, 18, 9095 DOI: 10.1039/D0OB01989E

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Organic & Biomolecular Chemistry