Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2-Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides

被引：18

作者：

Chi, Yue ^{[1
]}

Xu, Ling ^{[1
]}

Du, Shanshan ^{[1
]}

Yan, Haihan ^{[1
]}

Zhang, Wen-Xiong ^{[1
,2
]}

Xi, Zhenfeng ^{[1
]}

机构：

[1] Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Coll Chem,Minist Educ, Beijing 100871, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 29期

关键词：

amino acid esters; carbodiimides; cyclic oxoguanidines; cyclization; guanylation; SOLID-PHASE SYNTHESIS; EARTH-METAL COMPLEXES; N-H BONDS; C-H; SUBSTITUTED GUANIDINES; CATALYTIC ADDITION; SELECTIVE SYNTHESIS; EFFICIENT ROUTE; 2,3,5-TRISUBSTITUTED 4H-IMIDAZOLONES; BENZIMIDAZOLE DERIVATIVES;

D O I：

10.1002/chem.201500573

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：10369 / 10378

页数：10

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