2,4,6-Trihydroxybenzoic Acid-Catalyzed Oxidative Ugi Reactions with Molecular Oxygen via Homo- and Cross-Coupling of Amines
2,4,6-Trihydroxybenzoic Acid-Catalyzed Oxidative Ugi Reactions with Molecular Oxygen via Homo- and Cross-Coupling of Amines
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DOI：
10.1021/acs.joc.9b01422
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发表时间：
2019-09-20
影响因子：
3.6
通讯作者：
Ogawa, Akiya
中科院分区：
文献类型：
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作者：
Dong, Chun-ping;Uematsu, Akinori;Ogawa, Akiya
以2，4，6-三羟基苯甲酸为催化剂，在O-2气氛下，由两种不同的胺、异腈和羧酸进行无金属氧化四组分Ugi反应（U-4CRs），合成了二肽。有机催化的U-4CR通过苄胺与其他脂肪族或芳香族胺的氧化交叉偶联以形成亚胺，然后与异腈和羧酸缩合来进行。通过胺的交叉偶联的U-4CR是罕见的，并且简单的、无金属的程序有利于在药物和杂环合成中的进一步应用。
Metal-free, oxidative four-component Ugi reactions (U-4CRs) were conducted to synthesize dipeptides from two different amines, isocyanides, and carboxylic acids using 2,4,6-trihydroxybenzoic acid catalyst in O-2 atmosphere. The organocatalytic U-4CRs proceed via oxidative cross-coupling of benzylamines with other aliphatic or aromatic amines to form imines, followed by condensation with isocyanides and carboxylic acids. The U-4CRs via cross-coupling of amines are rare, and the simple, metal-free procedures are advantageous for further applications in drug and heterocycle syntheses.