Whiting Ellis, Lanning Maryanna E, Scheenstra Jacob A, Fletcher Steven
School of Chemistry, University of Cardiff , Cardiff CF10 3AT, U.K.
J Org Chem. 2015 Jan 16;80(2):1229-34. doi: 10.1021/jo502396u. Epub 2014 Dec 24.
A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the target salicylonitriles in excellent yields. The chemistry exhibits a broad scope, and the salicylonitriles can be readily isolated by a simple acid-base workup. In addition to functioning as useful synthetic precursors, salicylonitriles may serve as more cell penetrable bioisosteres of carboxylic acids.
描述了一种温和且高效的一锅法程序，利用光延反应将水杨醛肟转化为水杨腈。反应通过相应的1,2-苯并异恶唑进行，该化合物原位发生肯普消除反应，以优异的产率生成目标水杨腈。该化学方法具有广泛的适用范围，水杨腈可通过简单的酸碱后处理轻松分离。除了作为有用的合成前体，水杨腈还可作为羧酸的更易穿透细胞的生物电子等排体。
