title: Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes.
abstract: 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.
authors.affiliation: School of Chemistry, University of Cardiff , Cardiff CF10 3AT, U.K.
authors.forename: Ellis
authors.initials: E
authors.lastname: Whiting
authors.forename: Maryanna E
authors.initials: ME
authors.lastname: Lanning
authors.forename: Jacob A
authors.initials: JA
authors.lastname: Scheenstra
authors.forename: Steven
authors.initials: S
authors.lastname: Fletcher
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002845:Chromatography; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D009570:Nitriles; D010091:Oximes; C005704:salicylaldoxime