Annulation-Triggered Denitrogenative Transformations of 2-(5-Iodo-1,2,3-triazolyl)benzoic Acids
Vladislav A. Voloshkin, Yury N. Kotovshchikov, Gennadij V. Latyshev, Nikolay V. Lukashev, I. P. Beletskaya
Abstract
The ability of [1,2,3]triazolobenzoxazinones to act as a source of “hidden” diazo group was discovered. These diazo precursors can be easily prepared by the intramolecular cyclization of 2-(5-iodo-1,2,3-triazolyl)benzoic acids. The Cu-catalyzed capture of the hidden diazo group allows for further functionalization through the denitrogenative pathway. The transformations proceed via the formation of either diazoimine or diazoamide intermediates. Novel routes to various anthranilamides as well as thiolated benzoxazinones were developed using the one-pot cyclization/diazo capture procedure.
Topics & Concepts
DiazoAnnulationChemistryIntramolecular forceCombinatorial chemistryBenzoic acidSurface modificationFunctional groupCatalysisMedicinal chemistryStereochemistryOrganic chemistryPolymerPhysical chemistryCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods