Lewis Acid Catalyzed Intramolecular Ring-Opening of Triazole-Substituted Methylenecyclopropanes: An Approach to 4H-[1,2,3]Triazolopyrazines and 4H-[1,2,3]Triazolo[1,4]diazepines

Run Sun; Di-Han Zhang; Min Shi

doi:10.1055/s-0034-1378977

Synlett, Table of Contents

Synlett 2014; 25(16): 2293-2296
DOI: 10.1055/s-0034-1378977

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Lewis Acid Catalyzed Intramolecular Ring-Opening of Triazole-Substituted Methylenecyclopropanes: An Approach to 4H-[1,2,3]Triazolopyrazines and 4H-[1,2,3]Triazolo[1,4]diazepines

Run Sun

^aKey Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China

,

Di-Han Zhang

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: mshi@mail.sioc.ac.cn

,

Min Shi*

^aKey Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: mshi@mail.sioc.ac.cn

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Abstract

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Abstract

A series of novel methylenecyclopropane-triazoles have been successfully prepared. Their intramolecular nucelophilic cyclizations have been explored in the presence of Yb(NTf₂)₃ catalyst, giving the corresponding triazole containing six- and seven-membered heterocycles in good yields upon heating in toluene.

Key words

triazole - methylenecyclopropanes - Lewis acid - intramolecular cyclization

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References

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