Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from 4-Trimethylsilyl-5-iodo-1,2,3-triazole

The investigation of synthetic methods involving 5-substituted 1,2,3-triazoles began several years ago when Lingjun Li was a PhD candidate at Peking University more than ten years ago. At that time, 4-amide-1,2,3-triazole was applied as the bioisostere of purine nucleobase for the design and synthesis of cyclic ADP-ribose analogues. However, there was no existing method to efficiently incorporate an iodine atom to the 5-position of 4-amide-1,2,3-triazole nucleobase at that time. Extensive studies have been undertaken over the last ten years establishing various tandem oxidative halogenation Cu-catalyzed alkyne azide cycloaddition strategies leading to 1,4-disubstituted 1,2,3-triazoles. In contrast, effective methods for the preparation of 1,5-disubtituted analogues were limited. Now, the groups of Lingjun Li and Guisheng Zhang (Henan Normal University, P. R. of China) developed a novel divergent synthetic protocol for 1,5-disubstituted 1,2,3-triazoles starting from 4-trimethylsilyl-5-iodo-1,2,3-triazole as precursor.

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