Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction

Wenkun Chen; Wen Yang; Ruihua Wu; Dingqiao Yang

doi:10.1039/C7GC03772D

Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction

Wenkun Chen, Wen Yang, Ruihua Wu and Dingqiao Yang

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.

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Publication details

The article was received on 17 Dec 2017, accepted on 12 Apr 2018 and first published on 13 Apr 2018

Article type: Paper

DOI: 10.1039/C7GC03772D

Citation: Green Chem., 2018, Accepted Manuscript

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Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction

W. Chen, W. Yang, R. Wu and D. Yang, Green Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7GC03772D
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Green Chemistry

Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction

Abstract

Supplementary files

Publication details

Water-Promoted Synthesis of Fused Bicyclic Triazolines and Naphthols from Oxa(aza)bicyclic Alkenes and the Transformation via Novel Ring-Opening/Rearrangement Reaction

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