Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2-Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides
Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2-Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides
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Zn(OTf)(2) 催化的氨基酸酯和碳二亚胺鸟苷化/酰胺化环状氧代胍的合成及机理研究
DOI：
10.1002/chem.201500573
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发表时间：
2015-07-13
影响因子：
4.3
通讯作者：
Xi, Zhenfeng
中科院分区：
文献类型：
--
作者：
Chi, Yue;Xu, Ling;Xi, Zhenfeng
以容易获得的氨基酸酯和碳二亚胺为原料，实现了锌(OTf)(2)催化的鸟酰化/酰胺化反应，以中高产率得到了各种环状氧鸟苷类化合物，包括2-氨基-1H-咪唑-5(4H)-酮和2-氨基喹唑啉-4(3H)-酮。这是第一次将铵盐用于鸟苷化反应。探索了环氧鸟苷类化合物通过氧化生成CN或Aldol反应生成共轭杂环化合物的应用。通过对三个重要中间体的分离和表征，很好地阐明了反应机理。
The Zn(OTf)(2)-catalyzed guanylation/amidation from readily available amino acid esters and carbodiimides is achieved to provide efficiently various cyclic oxoguanidines, including 2-amino-1H-imidazol-5(4H)-ones and 2-aminoquinazolin-4(3H)-ones in medium-to-high yields. It is the first time that an ammonium salt has been used in a guanylation reaction. The application of cyclic oxoguanidines to provide the conjugated heterocyclic compounds via oxidative CN formation or aldol reaction is explored. The reaction mechanism is well elucidated by the isolation and characterization of three important intermediates.