A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane.
A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane.
复制标题
DOI：
10.1021/jo5013288
复制
发表时间：
2014-09
期刊：
影响因子：
--
通讯作者：
N. Mani;A. Fitzgerald
中科院分区：
文献类型：
--
作者：
N. Mani;A. Fitzgerald
描述了一种分子内1，3-偶极环加成策略，该策略不依赖于传统的Cu（1）催化的叠氮-炔环加成反应，可快速进入三唑稠合的杂环化合物。该策略的核心是在原位生成取代的重氮甲烷，在一个两步序列从相应的醛，然后进行顺利的环加成与氰基，以产生所需的稠合的1，2，3-三唑在良好的总产率。整个序列可以在一锅操作中进行。
An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a one-pot operation.