Trifluoroacetic Acid-Mediated Denitrogenative <i>ortho</i>-Hydroxylation of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Metal-Free Approach
Kanagaraj Madasamy, Madasamy Hari Balakrishnan, Ramaraju Korivi, Subramaniyan Mannathan
Abstract
An efficient trifluoroacetic acid-mediated denitrogenative hydroxylation of 1,2,3-benzotriazin-4(3H)-ones is described. This metal-free approach is compatible with a wide range of 1,2,3-benzotriazin-4(3H)-ones, affording ortho-hydroxylated benzamides in good to high yields with a short reaction time. The reaction is believed to proceed via a benzene diazonium intermediate. The synthetic utility of the reaction was successfully demonstrated by the preparation of an antimicrobial drug, Riparin C, and benzoxazine-2,4(3H)-diones in good yields.
Topics & Concepts
Trifluoroacetic acidChemistryHydroxylationMedicinal chemistryCombinatorial chemistryBenzeneMetalOrganic chemistryStereochemistryEnzymePhenothiazines and Benzothiazines Synthesis and ActivitiesCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions