Synthesis of fused and linked bicyclic nitrogen heterocycles by palladium-catalyzed domino cyclization of propargyl bromides.
Synthesis of fused and linked bicyclic nitrogen heterocycles by palladium-catalyzed domino cyclization of propargyl bromides.
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DOI：
10.1002/chem.201000653
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发表时间：
2010-07
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通讯作者：
Akinori Okano;K. Tsukamoto;Shohei Kosaka;H. Maeda;S. Oishi;Tetsuaki Tanaka;N. Fujii;H. Ohno
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文献类型：
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作者：
Akinori Okano;K. Tsukamoto;Shohei Kosaka;H. Maeda;S. Oishi;Tetsuaki Tanaka;N. Fujii;H. Ohno
本文报道了钯(0)催化的双环杂环化合物的直接构筑。用催化剂[Pd(PPh(3))(4)]处理具有亲核官能团并由两个或三个碳原子连接的炔丙基溴化物，得到了高产率的双环化产物。当使用具有适当亲核基团的底物时，可以选择性地获得所需的双环杂环。我们还描述了在无碱条件下，2-烷基氮杂环丁烷与催化量[Pd(PPh(3))(4)]的反应，得到了与相应的炔丙基溴化物相同的稠合杂环。
The palladium(0)-catalyzed direct construction of bicyclic heterocycles is described. Treatment of propargyl bromides that have nucleophilic functional groups connected by two or three carbon atoms with catalytic [Pd(PPh(3))(4)] affords bis-cyclization products in good yields. The desired bicyclic heterocycles can be obtained selectively when using substrates with appropriate nucleophilic groups. We also describe the reaction of a 2-alkynylazetidine derivative with a catalytic amount of [Pd(PPh(3))(4)] under base-free conditions, which affords the same fused heterocycles as the corresponding propargyl bromides.