Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
Storm Hassell‐Hart, Elisa Speranzini, Sirihathai Srikwanjai, Euan J. Hossack, S. Mark Roe, D. Fearon, Daniel Akinbosede, S. Hare, John Spencer
Abstract
A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.
Topics & Concepts
ChemistryThiazoleYlideSubstituentCatalysisCombinatorial chemistryIridiumInsertion reactionStereochemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsClick Chemistry and Applications