Synthesis and Characterization of series of 1-((4-Phenyl-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazoles

A new series of 1-[(4-aryl-1H-imidazol-1-yl) methyl]-1 H -1, 2, 3-triazoles (6a–m) were prepared by an easy and effective synthesis approach. First, 4-bromo-1 H -imidazole (1) was N-propargylated with 3-bromoprop-1-yne (2) to produce 4-bromo-1-(prop-2-yn-1-yl)-1 H -imidazole (3). The corresponding 4-aryl-1-(prop-2-yn-1-yl)-1 H -imidazoles(5a–m) were obtained in good to outstanding yields by Suzuki–Miyaura cross-coupling the crucial intermediate 3 with different substituted arylboronic acids (4a–m). Lastly, the target 1-[(4-aryl-1H-imidazol-1-yl) methyl]-1 H -1, 2, 3-triazoles (6a–m) was obtained by regioselective azide–alkyne cycloaddition employing sodium azide. Rapid access to structurally varied imidazole–triazole hybrids for additional biological and medicinal chemistry research is made possible by the established technology, which is operationally straightforward, effective, and widely adaptable. (Scheme I& Table 1-4)

Key words:4-Bromo-1H-imidazole, Suzuki–Miyaura cross-coupling, Click chemistry, 1,2,3-Triazoles, Imidazole–triazole hybrids.