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

J Org Chem

State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.

Published: May 2024

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 I/CuI system. This approach represents a significant departure from traditional methods for synthesizing polysubstituted imidazoles; it employs the I/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.

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http://dx.doi.org/10.1021/acs.joc.3c02968DOI Listing

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