Issue 11, 2022
From the journal:

Organic Chemistry Frontiers

Switchable assembly of substituted pyrimidines and 2H-imidazoles via Cu(i)-catalysed ring expansion of 2 methoxyl-2H-azirines†

Shaofa Sun,‡a   Jie Huang, ORCID logo ‡a   Cheng Yuan,a   Gangqiang Wang,*ab   Donghui Guoc  and  Jian Wang ORCID logo *ac  

* Corresponding authors

a Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Non-power Nuclear Technology Collaborative Innovation Center, School of Nuclear Technology and Chemistry & Biology, Hubei University of Science and Technology, Xianning, China

b School of Pharmaceutical Sciences, South-Central MinZu University, Wuhan, China

c School of Pharmaceutical Sciences, Tsinghua University, Beijing, China
E-mail: wangjian2012@tsinghua.edu.cn

Abstract

The unprecedented switchable synthesis of substituted pyrimidines and 2H-imidazoles via the Cu(I)-catalyzed ring expansion of 2-methoxyl-2H-azirines is described. This protocol features broad substrate scope and allows the rapid assembly of amides. Notably, this process includes the selective cleavage of the C–N bond or C–C bond of 2H-azirines with [3 + 2] or [3 + 3] annulation.

Graphical abstract: Switchable assembly of substituted pyrimidines and 2H-imidazoles via Cu(i)-catalysed ring expansion of 2 methoxyl-2H-azirines

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Article information

DOI
https://doi.org/10.1039/D2QO00341D
Article type
Research Article
Submitted
01 Mar 2022
Accepted
15 Apr 2022
First published
20 Apr 2022

Org. Chem. Front., 2022,9, 3006-3011

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Switchable assembly of substituted pyrimidines and 2H-imidazoles via Cu(I)-catalysed ring expansion of 2 methoxyl-2H-azirines

S. Sun, J. Huang, C. Yuan, G. Wang, D. Guo and J. Wang, Org. Chem. Front., 2022, 9, 3006 DOI: 10.1039/D2QO00341D

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