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

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

Yoona Song, Soyun Lee, Palash Dutta, Jae Sang Ryu

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH ₂ 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.

Original language	English
Pages (from-to)	744-754
Number of pages	11
Journal	Synthesis (Germany)
Volume	52
Issue number	5
DOIs	https://doi.org/10.1055/s-0039-1691506
State	Published - 3 Mar 2020

Bibliographical note

Publisher Copyright:
© 2020 Georg Thieme Verlag. All rights reserved.

Keywords

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

Access to Document

10.1055/s-0039-1691506

Cite this

@article{f79c58c5237d4615a7f1a7617e931c22,

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

abstract = "A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH 2 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.",

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

author = "Yoona Song and Soyun Lee and Palash Dutta and Ryu, {Jae Sang}",

year = "2020",

month = mar,

day = "3",

doi = "10.1055/s-0039-1691506",

language = "English",

volume = "52",

pages = "744--754",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "5",

}

TY - JOUR

T1 - A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

AU - Song, Yoona

AU - Lee, Soyun

AU - Dutta, Palash

AU - Ryu, Jae Sang

PY - 2020/3/3

Y1 - 2020/3/3

N2 - A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH 2 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.

AB - A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH 2 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.

KW - 1,2,3-triazoles

KW - click reactions

KW - copper catalyst

KW - multicomponent reactions

KW - one-pot reactions

UR - http://www.scopus.com/inward/record.url?scp=85079693520&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1691506

DO - 10.1055/s-0039-1691506

M3 - Article

AN - SCOPUS:85079693520

SN - 0039-7881

VL - 52

SP - 744

EP - 754

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 5

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this