One‐Pot Synthesis of 5‐Amino‐1,2,3‐triazole Derivatives via Dipolar Azide−Nitrile Cycloaddition and Dimroth Rearrangement under Solvent‐Free Conditions

An efficient one‐pot methodology for the preparation of 5‐amino‐1,2,3‐triazole derivatives based on the combination of dipolar azide−nitrile cycloaddition with Dimroth rearrangement under solvent‐free conditions has been developed. A series of novel 5‐amino‐1,2,3‐triazole derivatives has been synthe...

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Published inEuropean journal of organic chemistry Vol. 2021; no. 9; pp. 1378 - 1384
Main Authors Gribanov, Pavel S., Atoian, Edita M., Philippova, Anna N., Topchiy, Maxim A., Asachenko, Andrey F., Osipov, Sergey N.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.03.2021
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Cycloaddition
Heterocycles
Physical Sciences
Science & Technology
Solvents
Synthetic methods
Triazoles
Heterocycles
SUZUKI
CATALYZED CYCLOADDITION
1,2,3-TRIAZOLE
N-TOSYLHYDRAZONES
ANTICANCER ACTIVITY
CROSS-COUPLING REACTIONS
Cyclization
Triazoles
REGIOSELECTIVE SYNTHESIS
Synthetic methods
ARYL AZIDES
METAL-FREE
ALKYNE CYCLOADDITION
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ISSN1434-193X
1099-0690
DOI10.1002/ejoc.202001620

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Summary:An efficient one‐pot methodology for the preparation of 5‐amino‐1,2,3‐triazole derivatives based on the combination of dipolar azide−nitrile cycloaddition with Dimroth rearrangement under solvent‐free conditions has been developed. A series of novel 5‐amino‐1,2,3‐triazole derivatives has been synthesized by combining a dipolar azide−nitrile cycloaddition with a Dimroth rearrangement under solvent‐free conditions. Solvent‐free approach for the synthesis of 5‐amino‐1,2,3‐triazoles is reported for the first time.
Bibliography:Russian Science Foundation
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SourceType-Scholarly Journals-1
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ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001620