Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction
Abstract
An efficient three-component domino reaction between oxa(aza)bicyclic alkenes, sodium azide, and primary haloalkanes is reported, which offers a mild access to 1,2,3-triazolines in an aqueous medium with excellent diastereoselectivities and yields. Further studies show that, an water-promoted isomerization of oxa(aza)bicyclic alkenes can afford 1-naphthol derivatives in good yields. Water not only promote the reaction, but also provide the recyclable and sustainable approach to the desired product. In addition, a novel metal-free cascade ring-opening/rearrangement reaction of the obtained bicyclic triazolines to multifunctionalized indenes has been discovered.