Synthesis of 1-Benzyl-2,4-diarylimidazole through I2/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Ting-Kang Lv; Si Chen; Yi-Xuan Lu; Bao-Hua Chen

doi:10.1021/acs.joc.3c02968

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

J Org Chem. 2024 May 17;89(10):6723-6728. doi: 10.1021/acs.joc.3c02968. Epub 2024 May 1.

Authors

Ting-Kang Lv¹, Si Chen², Yi-Xuan Lu¹, Bao-Hua Chen¹

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
² School of Chemical Engineering, Lanzhou University of Arts and Sciences, Lanzhou, Gansu 730000, P. R. China.

PMID: 38691828
DOI: 10.1021/acs.joc.3c02968

Abstract

In this paper, we report an innovative method for synthesizing 1-benzyl-2,4-diarylimidazole utilizing 1-phenylethanone-2-(2-pyridinyl) hydrazine and benzylamine, catalyzed by an I₂/CuI system. This approach represents a significant departure from traditional methods for synthesizing polysubstituted imidazoles; it employs the I₂/CuI catalyst to replace rare metal catalysts, thereby achieving high yields of substitution products (≤85%). This method for the generation of 1,2,4-triimidazole derivatives is characterized by its exceptional chemical selectivity and extensive substrate compatibility.