Synthesis of 5-halogenated 1,2,3-triazoles under stoichiometric Cu(I)-mediated azide-alkyne cycloaddition (CuAAC or ¡®Click Chemistry¡¯)

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• 作者：David Goyard ; Jean-Pierre Praly ; Sé ; bastien Vidal ; ^{sebastien.vidal@univ-lyon1.fr}
• 关键词：1 ; 3-Dipolar cycloaddition ; 1 ; 2 ; 3-Triazole ; Atropoisomer ; Click Chemistry ; Catalysis
• 刊名：Carbohydrate Research
• 出版年：2012
• 出版时间：15 November, 2012
• 年：2012
• 卷：362
• 期：Complete
• 页码：79-83
• 全文大小：571 K

文摘

Glucosylated heterocycles have been identified as potent inhibitors of glycogen phosphorylase (GP), a biomolecular target for the treatment of hyperglycemia and therefore type 2 diabetes. Several glucosylated triazoles have been evaluated as GP inhibitors and additional structures are being considered in the present study with the introduction of a substituent at the 5-position of the triazole ring. The 1,3-dipolar cycloaddition of azide and alkyne using stoichiometric amounts of Cu(I) halides favored the formation of the 5-halogenated 1,2,3-triazoles. The influence of the copper halide introduced (CuI, CuBr, or CuCl) provided different results and more specifically for the CuCl system which afforded a dimeric 5,5¡ä-bistriazole in good yield (56 % ) as evidenced by crystallographic data.