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

Wenkun Chen,^a Wen Yang,^a Ruihua Wu^a and Dingqiao Yang*^a

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* Corresponding authors

^a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
E-mail: yangdq@scnu.edu.cn
Fax: +86 20 31040403
Tel: +86 20 31040403

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.

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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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Green Chemistry

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

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