Synthesis of 4-Monosubstituted 1,2,3-Triazoles

Liguo Teng; Shuitao Zhang; Tiebo Xiao; Baomin Yang; Yubo Jiang

doi:10.7536/PC231017

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Prog Chem ›› 2024, Vol. 36 ›› Issue (7) : 1014-1025. DOI: 10.7536/PC231017

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Synthesis of 4-Monosubstituted 1,2,3-Triazoles

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Abstract

1,2,3-Triazoles are a kind of five-membered N-heterocycles featured with unique properties in biology and material science.They have played more and more important roles in the fields of medicine,pesticide,and materials since the Cu-catalyzed diploar cycloaddition reaction of azide and alkyne was founded by Sharpless and Medal groups,respectively.4-Monosubstituted 1,2,3-triazole is considerably important in its family,especially because of its structural merits of widely facile modifications.The synthesis of 4-monosubstituted 1,2,3-triazoles based on different reaction types and substrates,including cycloaddition of alkyne with azide,cycloaddition of nitroolefin with azide,cyclization of hydrazone with amino derivatives,and N¹-substituent removal of 1,4-disubstituted 1,2,3-triazoles are reviewed.The substrate scope,limitation,and representative mechanism are also discussed 。

Contents

1 Introduction

2 Progress in the synthesis of 4-monosubstituted 1,2,3-triazoles

2.1 1,3-Dipolar cycloaddition of alkyne and azide

2.2[3+2]Cycloaddition of nitroolefin and azide

2.3 Cyclization of hydrazone with amino derivative

2.4 Removal of N¹-substituent from 1,4-disubstituted 1,2,3-triazole

2.5 Reaction of alkenyl bromide with sodium azide

2.6 Other methods

3 Conclusion and outlook

Key words

4-monosubstituted 1,2,3-triazoles / synthesis / cycloaddition / cyclization / substituent removal

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Liguo Teng , Shuitao Zhang , Tiebo Xiao , et al . Synthesis of 4-Monosubstituted 1,2,3-Triazoles[J]. Progress in Chemistry. 2024, 36(7): 1014-1025 https://doi.org/10.7536/PC231017

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