Synthesis of fused 1,2,3-triazoles through carbocation-mediated intramolecular [3+2] cycloaddition of azido-propargyl alcohols

Youlai Zhang; Junru Li; Mengdi Wang; Huan Zhang; Hiroki Tanimoto; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.3987/COM-17-13763

Synthesis of fused 1,2,3-triazoles through carbocation-mediated intramolecular [3+2] cycloaddition of azido-propargyl alcohols

Youlai Zhang, Junru Li, Mengdi Wang, Huan Zhang, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi

生体認識化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

6 被引用数 (Scopus)

抄録

A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide-alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.

本文言語	英語
ページ（範囲）	1775-1782
ページ数	8
ジャーナル	Heterocycles
巻	94
号	9
DOI	https://doi.org/10.3987/COM-17-13763
出版ステータス	出版済み - 2017

ASJC Scopus 主題領域

分析化学
薬理学
有機化学

文献へのアクセス

10.3987/COM-17-13763

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引用スタイル

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title = "Synthesis of fused 1,2,3-triazoles through carbocation-mediated intramolecular [3+2] cycloaddition of azido-propargyl alcohols",

abstract = "A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide-alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.",

author = "Youlai Zhang and Junru Li and Mengdi Wang and Huan Zhang and Hiroki Tanimoto and Tsumoru Morimoto and Kiyomi Kakiuchi",

note = "Publisher Copyright: {\textcopyright} 2017 The Japan Institute of Heterocyclic Chemistry.",

year = "2017",

doi = "10.3987/COM-17-13763",

language = "英語",

volume = "94",

pages = "1775--1782",

journal = "Heterocycles",

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TY - JOUR

T1 - Synthesis of fused 1,2,3-triazoles through carbocation-mediated intramolecular [3+2] cycloaddition of azido-propargyl alcohols

AU - Zhang, Youlai

AU - Li, Junru

AU - Wang, Mengdi

AU - Zhang, Huan

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Kakiuchi, Kiyomi

PY - 2017

Y1 - 2017

N2 - A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide-alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.

AB - A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide-alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.

UR - http://www.scopus.com/inward/record.url?scp=85029415494&partnerID=8YFLogxK

U2 - 10.3987/COM-17-13763

DO - 10.3987/COM-17-13763

M3 - 学術論文

AN - SCOPUS:85029415494

SN - 0385-5414

VL - 94

SP - 1775

EP - 1782

JO - Heterocycles

JF - Heterocycles

IS - 9

ER -