Tandem Strecker/C(sp3)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH4SCN as a cyanating agent

Qing Yang; Xiao-Tong Yan; Cheng-Tao Feng; De-Xiang Chen; Zhong-Zhong Yan; Kun Xu

doi:10.1039/D1QO01060C

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Tandem Strecker/C(sp³)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH₄SCN as a cyanating agent†

Qing Yang,^ac Xiao-Tong Yan,^c Cheng-Tao Feng,

*^ac De-Xiang Chen,^c Zhong-Zhong Yan^c and Kun Xu

*^b

Author affiliations

* Corresponding authors

^a School of Pharmacy, Anhui University of Chinese Medicine; Anhui academy of Chinese medicine, Hefei, China
E-mail: fengct@mail.ustc.edu.cn

^b Faculty of Environment and Life, Beijing University of Technology, Beijing, China
E-mail: kunxu@bjut.edu.cn

^c Anhui University of Science and Technology, Huainan, China

Abstract

An I₂O₅ promoted tandem Strecker/C(sp³)–H amination reaction of pyridine-2-carboxaldehydes, benzylamines and NH₄SCN has been reported. This multicomponent reaction that allows the single-step construction of biologically important cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity was realized for the first time. Moreover, the use of safe and easy-to-handle NH₄SCN as a surrogate cyanating agent makes this protocol appealing for potential applications.

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Article information

DOI: https://doi.org/10.1039/D1QO01060C
Article type: Research Article
Submitted: 25 Jul 2021
Accepted: 19 Sep 2021
First published: 21 Sep 2021

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Org. Chem. Front., 2021,8, 6384-6389

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Tandem Strecker/C(sp³)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH₄SCN as a cyanating agent

Q. Yang, X. Yan, C. Feng, D. Chen, Z. Yan and K. Xu, Org. Chem. Front., 2021, 8, 6384 DOI: 10.1039/D1QO01060C

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