Cp*CoIII-catalyzed formal [4 + 2] cycloaddition of 2-phenyl-1H-imidazoles to afford imidazo[1,2-c]quinazoline derivatives

Deyu Wu; Zhengqiang Liu; Yiting Chang; Jiajing Chen; Haixiang Qi; Yi Dong; Heng Xu

doi:10.1039/D2OB00697A

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Cp*Co^III-catalyzed formal [4 + 2] cycloaddition of 2-phenyl-1H-imidazoles to afford imidazo[1,2-c]quinazoline derivatives†

Deyu Wu,^ab Zhengqiang Liu,^ab Yiting Chang,^ab Jiajing Chen,^ab Haixiang Qi,^ab Yi Dong

*^abc and Heng Xu

*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
E-mail: dongyi@imm.ac.cn, xuheng@imm.ac.cn

^b Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

^c State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medcial University, Guiyang 550014, China

Abstract

A synthetic protocol based on Cp*Co^III-catalyzed C–H amidation/annulation of 2-aryl-1H-imidazoles with 1,4,2-dioxazol-5-ones was developed to give imidazo[1,2-c]quinazoline derivatives with broad substrate scope in moderate to good yields. The method has good prospects of application in the synthesis of imidazo[1,2-c]quinazoline drugs.

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Article information

DOI: https://doi.org/10.1039/D2OB00697A
Article type: Paper
Submitted: 14 Apr 2022
Accepted: 08 Jun 2022
First published: 08 Jun 2022

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Org. Biomol. Chem., 2022,20, 4993-4998

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Cp*Co^III-catalyzed formal [4 + 2] cycloaddition of 2-phenyl-1H-imidazoles to afford imidazo[1,2-c]quinazoline derivatives

D. Wu, Z. Liu, Y. Chang, J. Chen, H. Qi, Y. Dong and H. Xu, Org. Biomol. Chem., 2022, 20, 4993 DOI: 10.1039/D2OB00697A

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Organic & Biomolecular Chemistry