通过一步柯提斯重排反应制备Boc保护的1-(3-氧代环烷基)脲：反应机理与范围
Boc-protected 1-(3-oxocycloalkyl)ureas via a one-step Curtius rearrangement: mechanism and scope.
作者信息
Sun Xianyu, Rai Rachita, Deschamps Jeffrey R, Mackerell Alexander D, Faden Alan I, Xue Fengtian
机构信息
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201 ; College of Animal Science and Technique, Heilongjiang Bayi Agriculture University, Daqing 163319, Heilongjiang, PR China.
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201.
出版信息
Tetrahedron Lett. 2014 Jan 22;55(4):842-844. doi: 10.1016/j.tetlet.2013.12.021.
1-(3-Oxocyclobutyl) carboxylic acid () was converted into -Boc-protected 1-(3-oxocyclobutyl) urea (), a key intermediates for the preparation of agonists of metabotropic glutamate receptor 5, in one-step when treated with diphenyl phosphoryl azide and triethylamine in -butanol. The mechanism of the reaction involves a nucleophilic addition of the generated -butyl carbamate to the isocyanate intermediate. This reaction is applicable to other 1-(3-oxocycloalkyl) carboxylic acids but not to linear -keto carboxylic acids.
1-（3-氧代环丁基）羧酸（）在用二苯基磷酰叠氮化物和三乙胺于正丁醇中处理时，一步转化为用于制备代谢型谷氨酸受体5激动剂的关键中间体——N-Boc保护的1-（3-氧代环丁基）脲（）。该反应的机理涉及生成的正丁基氨基甲酸酯对异氰酸酯中间体的亲核加成。此反应适用于其他1-（3-氧代环烷基）羧酸，但不适用于直链β-酮羧酸。
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