Facile and Quantitative Synthesis of 1,3-Diazaheterocycle-Fused 1,2,3-Triazole Derivatives Using Fluoroalkanesulfonyl Azide as a Diazo Transfer Reagent

A series of 1,3-diazaheterocycle-fused 1,2,3-triazoles were conveniently and quantitatively prepared by 1,3-dipolar cycloaddition of heterocyclic ketene aminals with fluoroalkanesulfonyl azide, followed by elimination of fluoroalkanesulfonyl amide at room temperature without any catalyst.

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 11; pp. 1717 - 1722
Main Authors Gu, Jiwei, Xiong, Wanting, Zhang, Zhenhua, Zhu, Shizheng
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
fluoroalkanesulfonyl azide
ketene aminals
heterocycles
ONE-POT SYNTHESIS
ANALOGS
ARYL AZIDES
AGENTS
HETEROCYCLIC KETENE AMINALS
INHIBITORS
1,3-diazaheterocycle-fused 1,2,3-triazole
BETA-ENAMINO ESTERS
1,3-dipolar cycloaddition
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Summary:A series of 1,3-diazaheterocycle-fused 1,2,3-triazoles were conveniently and quantitatively prepared by 1,3-dipolar cycloaddition of heterocyclic ketene aminals with fluoroalkanesulfonyl azide, followed by elimination of fluoroalkanesulfonyl amide at room temperature without any catalyst.
ISSN:0039-7881
DOI:10.1055/s-0030-1260043