Issue 14, 2021

Photocatalyzed intermolecular amination for the synthesis of hydrazonamides

Abstract

Hydrazonamides are fundamental building blocks in many pharmaceuticals and agricultural chemicals. Although previous transformations have been accomplished through multi-step reactions under harsh conditions, developing highly efficient synthetic strategies remains challenging. Considering the structural characteristic of hydrazonamides, a sequential multi-component reaction of β-ketonitriles with N,N-disubstituted hydrazines is designed and developed through a photocatalyzed intermolecular amination process. This work reports the first example of the use of N,N-disubstituted hydrazines as two different “amine” sources, characterized by isotope labeling experiments. The C–CN/N–N bonds are cleaved and new C–N/C[double bond, length as m-dash]N bonds are constructed in a one-pot reaction. This protocol can be carried out without the addition of any external metals, ligands, bases, oxidants and reductants, and possesses the advantages of operational simplicity, mild reaction conditions, and good functional group tolerance. Furthermore, this approach enables late-stage modifications of structurally complex bioactive molecules, natural products and drugs, thus showing potential applications in the field of organo-pharmaceutical chemistry.

Graphical abstract: Photocatalyzed intermolecular amination for the synthesis of hydrazonamides

Supplementary files

Article information

Article type
Research Article
Submitted
01 Mar 2021
Accepted
01 May 2021
First published
12 May 2021

Org. Chem. Front., 2021,8, 3838-3846

Photocatalyzed intermolecular amination for the synthesis of hydrazonamides

W. Guo, L. Cai, Z. Xie, W. Mei, G. Liu, L. Deng, X. Zhuo, Y. Zhong, X. Zou, L. Zheng and X. Fan, Org. Chem. Front., 2021, 8, 3838 DOI: 10.1039/D1QO00338K

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