Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide–alkene cascade reaction

Yu-Yang Xie, Ying-Chun Wang, Yan He, Da-Chao Hu, Heng-Shan Wang, Ying-Ming Pan
  • Green Chemistry, January 2017, Royal Society of Chemistry
  • DOI: 10.1039/c6gc01553k

What is it about?

Benzyl bromides bearing an ortho-substituted α,β-unsaturated ketone moiety are found to be promising precursors for the synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide– alkene cascade reaction under catalyst free conditions. Fused 1,2,3-triazole derivatives 2 were synthesized in excellent yields by treating compounds 1 with sodium azide in DMF at room temperature, whereas isoindoline derivatives 3 were produced in moderate to good yields only by slight modification of the reaction conditions. Both reactions call for simple and mild conditions, display broad substrate scopes and result in good regiospecificity.

Why is it important?

A convenient, efficient and regioselective method has been developed for the synthesis of fused 1,2,3-triazole and isoindoline derivatives using benzyl bromides bearing an orthosubstituted α,β-unsaturated ketone moiety under catalyst free conditions.

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http://dx.doi.org/10.1039/c6gc01553k

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