[3+2] Cycloaddition of o-nitrophenyl azide to 3a,6-epoxyisoindoles

[3+2] Cycloaddition of o-nitrophenyl azide to the multiple bond of oxabicyclo[2.2.1]heptene moiety in substituted 3a,6-epoxyisoindoles was performed. The 1,3-dipolar addition reaction proceeded stereoselectively, producing a pair of isomeric cis-4,8a-epoxy[1,2,3]triazolo[4,5-e]isoindoles. This approach demonstrated synthetic access to isomeric epoxy-1,2,3-benzotriazoles fused with a γ-butyrolactam moiety. © 2018, Springer Science+Business Media, LLC, part of Springer Nature.