Issue 26, 2019
From the journal:

Chemical Communications

Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles†

Jinxiong Cai,a   Haijie Bai,a   Yuan Wang,a   Xianxiu Xu, ORCID logo b   Haiming Xie ORCID logo *a  and  Jun Liu ORCID logo *a  

* Corresponding authors

a National & Local United Engineering Laboratory for Power Battery, Department of Chemistry, Northeast Normal University, Changchun, China
E-mail: liuj975@nenu.edu.cn, xiehm136@nenu.edu.cn

b College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science, Shandong Normal University, Jinan, China

Abstract

A novel base-mediated regioselective [3+2] annulation of active methylene isocyanides with ketenimines has been developed. In the presence of t-BuOK, a wide range of ketenimines readily react with active methylene isocyanides in DMF at 40 °C to afford 1,4,5-trisubstituted imidazoles efficiently.

Graphical abstract: Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles

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Article information

DOI
https://doi.org/10.1039/C9CC01257E
Article type
Communication
Submitted
13 Feb 2019
Accepted
07 Mar 2019
First published
08 Mar 2019

Chem. Commun., 2019,55, 3821-3824

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Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles

J. Cai, H. Bai, Y. Wang, X. Xu, H. Xie and J. Liu, Chem. Commun., 2019, 55, 3821 DOI: 10.1039/C9CC01257E

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