Issue 9, 2022
From the journal:

Organic Chemistry Frontiers

Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons†

Wen Li,a   Mengqi Zhang,a   Jin Yan,a   Linying Ni,a   Hua Cao ORCID logo *a  and  Xiang Liu ORCID logo *a  

* Corresponding authors

a School of Chemistry and Chemical Engineering and Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Zhongshan 528458, China
E-mail: caohua@gdpu.edu.cn, liux96@gdpu.edu.cn

Abstract

A transition metal- and oxidant-free C–C/C–N annulation of azomethine imines with vinylene carbonate as dual synthons under simple reaction conditions is described herein. Depending on the structure of azinium-N-imines, vinylene carbonate could serve as an ethynol and acetylene surrogate, which results in the formation of pyrazolo[1,5-a]pyridine derivatives and pyrazolo[1,5-a]pyridin-2-ol derivatives through [3 + 2] cyclization. Importantly, this mild system tolerates a diverse array of heterocyclic N-imines such as quinolinium and isoquinolinium salts with good functional group compatibility.

Graphical abstract: Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons

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Article information

DOI
https://doi.org/10.1039/D2QO00308B
Article type
Research Article
Submitted
23 Feb 2022
Accepted
23 Mar 2022
First published
25 Mar 2022

Org. Chem. Front., 2022,9, 2529-2533

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Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons

W. Li, M. Zhang, J. Yan, L. Ni, H. Cao and X. Liu, Org. Chem. Front., 2022, 9, 2529 DOI: 10.1039/D2QO00308B

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