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Synthesis 2011(11): 1717-1722  
DOI: 10.1055/s-0030-1260043
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Jiwei Gu, Wanting Xiong, Zhenhua Zhang, Shizheng Zhu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhusz@sioc.ac.cn;
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Publication History

Received 28 February 2011
Publication Date:
13 May 2011 (online)

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Abstract

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.

Key words

fluoroalkanesulfonyl azide - ketene aminals - 1,3-dipolar cycloaddition - heterocycles - 1,3-diazaheterocycle-fused 1,2,3-triazole

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