Synthesis of Dihydro-3,1-benzoxazine Derivatives from 1,3-Amino Alcohols and <i>N</i>-Sulfonyl-1,2,3-triazole
Kavuri Rupa, Dongari Yadagiri, Ratnam Bagavathi, Pazhamalai Anbarasan
Abstract
An efficient rhodium-catalyzed synthesis of dihydro-3,1-benzoxazine derivatives has been accomplished from aniline-derived 1,3-amino alcohols and N -sulfonyl-1,2,3-triazole. The developed reaction demonstrates the new reactivity of azavinyl carbenes and allows access to diverse substituted dihydro-3,1-benzoxazines in good yields. Importantly, the reaction was readily extended to diols and could be used for selective protection of amino alcohols with N -sulfonyl-1,2,3-triazole as the protecting reagent.
Topics & Concepts
ChemistrySulfonylAnilineReagentReactivity (psychology)Combinatorial chemistry1,2,4-TriazoleOrganic chemistryRhodiumCatalysisMedicineAlkylPathologyAlternative medicineCyclopropane Reaction MechanismsClick Chemistry and ApplicationsCatalytic C–H Functionalization Methods