A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

Yoona Song; Soyun Lee; Palash Dutta; Jae-Sang Ryu

doi:10.1055/s-0039-1691506

Synthesis, Table of Contents

Synthesis 2020; 52(05): 744-754
DOI: 10.1055/s-0039-1691506

paper

A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

Authors

Yoona Song
Soyun Lee
Palash Dutta
Jae-Sang Ryu ∗

College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea Email: ryuj@ewha.ac.kr

Abstract

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^‡ These authors contributed equally to this work.

Abstract

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH₂ is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.

Key words

1,2,3-triazoles - multicomponent reactions - one-pot reactions - click reactions - copper catalyst

Full Text

References

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Supplementary Material

Supporting Information (PDF)