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Issue 11, 2018
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Water-promoted synthesis of fused bicyclic triazolines and naphthols from oxa(aza)bicyclic alkenes and transformation via a novel ring-opening/rearrangement reaction

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Abstract

An efficient three-component domino reaction among 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, water-promoted isomerization of oxa(aza)bicyclic alkenes can afford 1-naphthol derivatives in good yields. Water not only promotes the reaction, but also provides a 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 form multifunctionalized indenes has been discovered.

Graphical abstract: Water-promoted synthesis of fused bicyclic triazolines and naphthols from oxa(aza)bicyclic alkenes and transformation via a novel ring-opening/rearrangement reaction

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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., 2018,20, 2512-2518
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    Water-promoted synthesis of fused bicyclic triazolines and naphthols from oxa(aza)bicyclic alkenes and transformation via a novel ring-opening/rearrangement reaction

    W. Chen, W. Yang, R. Wu and D. Yang, Green Chem., 2018, 20, 2512
    DOI: 10.1039/C7GC03772D

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