title: A concomitant allylic azide rearrangement/intramolecular azide-alkyne cycloaddition sequence.
abstract: An intramolecular Huisgen cycloaddition of an interconverting set of isomeric allylic azides with alkynes affords substituted triazoles in high yield. The stereoisomeric vinyl-substituted triazoloxazines formed depend on the rate of cycloaddition of the different allylic azide precursors when the reaction is carried out under thermal conditions. In contrast, dimerized macrocyclic products were obtained when the reaction was done using copper(I)-catalyzed conditions, demonstrating the ability to control the reaction products through changing conditions.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas , Lawrence, Kansas 66045, United States.
authors.forename: Rakesh H
authors.initials: RH
authors.lastname: Vekariya
authors.forename: Ruzhang
authors.initials: R
authors.lastname: Liu
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D007454:Iodides; D014230:Triazoles; D003300:Copper; C073870:cuprous iodide