Synthesis of Hydroxamic Acid Derivatives Using Blocked (Masked) <i>O</i>-Isocyanate Precursors
Joshua S. Derasp, Erica A. Barbera, Niève Séguin, David D. Brzezinski, André M. Beauchemin
Abstract
Hydroxamic acids are present in a several pharmaceuticals and agrochemicals. Synthetic strategies providing access to hydroxamic acid derivatives remain limited, typically requiring the use of nucleophilic hydroxylamine reagents. Herein, a synthesis of hydroxamates from unactivated carboxylic acids is reported making use of rare blocked (masked) O-substituted isocyanates. The applicability of this transformation was highlighted by targeting the synthesis of vorinostat and belinostat derivatives.
Topics & Concepts
ChemistryHydroxamic acidHydroxylamineIsocyanateNucleophileCombinatorial chemistryReagentOrganic chemistryChemoselectivityCatalysisPolyurethaneSynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisClick Chemistry and Applications