Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications
Andreas Boelke, Thomas J. Kuczmera, Lucien D. Caspers, Enno Lork, Boris J. Nachtsheim
Abstract
The synthesis of iodolopyrazolium triflates via an oxidative cyclization of 3-(2-iodophenyl)-1H-pyrazoles is described. The reaction is characterized by a broad substrate scope, and various applications of these novel cyclic iodolium salts acting as useful synthetic intermediates are demonstrated, in particular in site-selective ring openings. This was finally applied to generate derivatives of the anti-inflammatory drug celecoxib. Their application as highly active halogen-bond donors is shown as well.
Topics & Concepts
ChemistryCombinatorial chemistryScope (computer science)Substrate (aquarium)HalogenRing (chemistry)StereochemistryOrganic chemistryComputer scienceGeologyAlkylProgramming languageOceanographySynthesis and Biological EvaluationSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions