A copper-catalyzed domino route toward purine-fused tricyclic derivatives.
A copper-catalyzed domino route toward purine-fused tricyclic derivatives.
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DOI：
10.1021/jo4025489
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发表时间：
2014-01
期刊：
影响因子：
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通讯作者：
M. Xie;Z. Chu;H. Niu;G. Qu;Haiming Guo
中科院分区：
文献类型：
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作者：
M. Xie;Z. Chu;H. Niu;G. Qu;Haiming Guo
首次通过铜催化的腺嘌呤与硝基烯烃的多米诺Michael/氧化交叉偶联反应合成了嘌呤稠合三环衍生物。该方法以空气为氧化剂，具有较高的区域选择性，为构建含两个新形成的C-N键的嘌呤核苷共轭体系提供了一条新的途径。同时，通过简单的还原反应，可以得到环外氨基嘌呤核苷，这可能会导致潜在的应用在荧光识别各种碱基在体内。
Purine-fused tricyclic derivatives have been synthesized via a copper-catalyzed domino Michael/oxidative cross-coupling reaction between adenines and nitroolefins for the first time. With air as the oxidant, this method has high regioselectivity, which provides a new route for constructing purine-nucleoside-conjugated systems with two newly formed C–N bonds. Meanwhile, purine nucleosides with an exocyclic amino group could be obtained easily by simple reduction, which may lead to potential applications in fluorescence recognition of various bases in vivo.