Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides.
Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides.
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DOI：
10.1021/acs.orglett.7b01602
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发表时间：
2017-07
期刊：
影响因子：
5.2
通讯作者：
Helena S Buchanan;Steven M. Pauff;Tilemachos D Kosmidis;A. Taladriz-Sender;Olivia I Rutherford;Marine Z C Hatit;Sabine Fenner;A. Watson;G. Burley
中科院分区：
文献类型：
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作者：
Helena S Buchanan;Steven M. Pauff;Tilemachos D Kosmidis;A. Taladriz-Sender;Olivia I Rutherford;Marine Z C Hatit;Sabine Fenner;A. Watson;G. Burley
描述了两种从 6-氯鸟苷获取 6-杂芳基 2-氨基嘌呤核糖核苷的 Pd 催化方法。首先，Pd-132 使用一系列硼底物和 6-氯鸟苷催化 Suzuki-Miyaura 交叉偶联，一步形成 6-杂芳基-2-氨基嘌呤。使用碘化钾作为添加剂的改良 Sonogashira 偶联进一步证明了 6-氯鸟苷的多功能性。最后，介绍了 6-炔基-2-氨基嘌呤核糖核苷在 [3 + 2] 环加成中作为亲偶极试剂的用途，当与叠氮化物和异腈 1,3-偶极子反应时分别产生三唑和异恶唑。
Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.