One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs2CO3-mediated addition/aromatization reaction

Chaoman Huang; Zefeng Jin; Bei Zhang; Yuanyuan Zhou; Huiting Lin; Honglan Kang; Guodong Shen; Xin Lv

doi:10.1039/D3OB00316G

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One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs₂CO₃-mediated addition/aromatization reaction†

Chaoman Huang,‡^a Zefeng Jin,‡^a Bei Zhang,^a Yuanyuan Zhou,^a Huiting Lin,

^a Honglan Kang,

^a Guodong Shen

^b and Xin Lv

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, People's Republic of China
E-mail: lvxin@zjnu.cn

^b School of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng 252059, Shandong, People's Republic of China

Abstract

A convenient one-pot assembly of 4-(imidazol-1-yl)indole derivatives from easily accessible o-alkynylanilines and imidazoles has been developed. The sequential dearomatization and Ag(I)-catalyzed cyclization/Cs₂CO₃-mediated conjugate addition/aromatization cascade reactions exhibit high efficiency and excellent selectivity. The combined use of a silver(I) salt and cesium carbonate is significant for facilitating this domino transformation. The 4-(imidazol-1-yl)indole products could be easily converted to the corresponding derivatives and might be valuable in biological chemistry and medicinal science.

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Article information

DOI: https://doi.org/10.1039/D3OB00316G
Article type: Paper
Submitted: 27 Feb 2023
Accepted: 25 Apr 2023
First published: 26 Apr 2023

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Org. Biomol. Chem., 2023,21, 4245-4256

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One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs₂CO₃-mediated addition/aromatization reaction

C. Huang, Z. Jin, B. Zhang, Y. Zhou, H. Lin, H. Kang, G. Shen and X. Lv, Org. Biomol. Chem., 2023, 21, 4245 DOI: 10.1039/D3OB00316G

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Organic & Biomolecular Chemistry