Expanding the substrate scope for C-H amination reactions: Oxidative cyclization of urea and guanidine derivatives
Expanding the substrate scope for C-H amination reactions: Oxidative cyclization of urea and guanidine derivatives
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DOI：
10.1021/ol052920y
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发表时间：
2006-03-16
期刊：
影响因子：
5.2
通讯作者：
Du Bois, J
中科院分区：
文献类型：
--
作者：
Kim, M;Mulcahy, JV;Du Bois, J
N-三氯乙氧基磺酰基保护的尿素和胍类化合物的氧化C-H胺化反应在叔基和苄基底物中进行得很好。这些反应的成功取决于选择了吸电子的2，2，2-三氯乙氧基磺酰(TCES)保护基团、工业催化剂Rh-2(Esp)(2)(1-2mo%)和甲苯作为溶剂。杂环咪唑烷-2-酮和2-氨基咪唑啉作为结构元素出现在天然产物和治疗设计分子中的频率使这些方法具有大量的潜在应用。
Oxidative C-H amination of N-trichloroethoxysulfonyl-protected ureas and guanidines is demonstrated to proceed in high yield for tertiary and benzylic-derived substrates. The success of these reactions is predicated on the choice of the electron-withdrawn 2,2,2-trichloroethoxysulfonyl (Tces) protecting group, the commercial catalyst Rh-2(esp)(2) (1-2 mol %), and toluene as solvent. The frequency with which the heterocyclic imidazolidin-2-ones and 2-aminoimidazolines appear as structural elements in both natural products and therapeutically designed molecules confers these methods with a large number of potential applications.