乌吉反应和帕瑟里尼反应类型偶联中的斯迈尔斯重排：通往O-和N-芳基酰胺的新型多组分合成方法
Smiles rearrangements in Ugi- and Passerini-type couplings: new multicomponent access to O- and N-arylamides.
作者信息
Kaïm Laurent El, Gizolme Marie, Grimaud Laurence, Oble Julie
机构信息
Laboratoire Chimie et procédés, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, Paris 75015, France.
出版信息
J Org Chem. 2007 May 25;72(11):4169-80. doi: 10.1021/jo070202e. Epub 2007 Apr 25.
The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.
在与缺电子酚类进行的乌吉（Ugi）和帕瑟里尼（Passerini）型偶联反应中使用斯迈尔斯重排反应，能够非常直接地通过多组分反应形成O-芳基酰胺和N-芳基酰胺。对于高度活化的邻硝基苯酚和对硝基苯酚，反应产率最佳，而水杨酸衍生物生成加合物的产率较低。通过羟基吡啶和羟基嘧啶等杂环酚类的成功偶联，进一步拓展了这些新反应的适用范围。
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