CuBr-NCS-Mediated Multicomponent Azide-Alkyne Cycloaddition: Mild and Efficient Synthesis of 5-Bromo-1,4-Disubstituted-1,2,3-Triazoles

CuBr-NCS-Mediated Multicomponent Azide-Alkyne Cycloaddition: Mild and Efficient Synthesis of 5-Bromo-1,4-Disubstituted-1,2,3-Triazoles
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DOI:
10.1055/s-0030-1259908
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发表时间:
2011-04-01
期刊:
影响因子:
2
通讯作者:
Zhang, Lihe
Zhang, Lihe
中科院分区:
化学4区
文献类型:
--
作者:
Li, Lingjun;Li, Ran;Zhang, Lihe

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结果表明,CuBr-NCS是一种温和、高效的反应体系,能促进多组分叠氮-炔环加成反应的进行。在该反应条件下,端炔和叠氮化物可以在室温下顺利反应,得到目标产物5-溴-1,4-二取代-1,2,3-三氮唑,产率中等到很好,对其他敏感官能团有广泛的容忍度。CuBr-NCS反应体系在糖和环腺苷5‘-二磷酸核糖(CADPR)类似物中的进一步成功应用表明了该方法在设计生物分子合成中的应用价值。
CuBr-NCS was found to be a mild and efficient reaction system to promote the multicomponent azide-alkyne cycloaddition reactions. Under the reaction conditions, terminal alkynes and azides can react smoothly at ambient temperature to give the target products 5-bromo-1,4-disubsituted-1,2,3-triazoles in moderate to good yields with a wide tolerance of other sensitive functional groups. The further successful application of the CuBr-NCS reaction system in sugar and cyclic adenosine 5'-diphosphoribose (cADPR) analogues illustrated the value of this method in the synthesis of designed biomolecules.