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Chemistry of 1,2,3-triazoles pp 51–116Cite as

Synthesis of 2H-1,2,3-Triazoles

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 40))

Abstract

This chapter gives an overview of methods for the synthesis of NH- and N(2)-substituted 1,2,3-triazoles, their advantages, lacks, scope, and limitations. Moreover, it will give some insights on the reaction mechanisms and will explain how different conditions and structure substrates can influence the direction for reactions. An extensive analysis for the last 20 years (starting at 1990) of NH-1,2,3-triazoles chemistry is presented. Some older data with high importance are also included.

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Abbreviations

Ac:

Acetyl

anhyd:

Anhydrous

Ar:

Aryl

B3LYP:

Becke three-parameter, Lee-Yang-Parr

Bn:

Benzyl

Bu:

Butyl

cat:

Catalyst

COSMO:

Conductor-like Screening MOdel

Cy:

Cyclohexyl

d:

Day(s)

dba:

Dibenzylideneacetone

DBU:

1,8-diazabicyclo [5.4.0]undec-7-ene

DCE:

Dichloroethane

DCM:

Dichloromethane

DEAD:

Diethyl azodicarboxylate

DFT:

Density Functional Theory

DIPA:

Diisopropyl amine

DMA:

Dimethylacetamide

DMAP:

4-(Dimethylamino)pyridine

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

dppp:

1,3-Bis(diphenylphosphino)propane

EDG:

Electron-donating group

equiv:

Equivalent(s)

EWG:

Electron-withdrawing group

Fc:

Ferrocenyl

GIAO:

Gauge Independent Atomic Orbital

h:

Hour(s)

Hex:

Hexyl

HMBC:

Heteronuclear Multiple Bond Coherence

i-Pr:

Iso-propyl

KHMDS:

Potassium hexamethyldisilazide potassium bis(trimethylsilyl)amide

LHMDS:

Lithium hexamethyldisilazide lithium bis(trimethylsilyl)amide

min:

Minute(s)

mol:

Mole(s)

MW:

Microwave irradiation

NICS:

Nucleus Independent Chemical Shifts

NMP:

N-methylpyridine

NOE:

Nuclear Overhauser effect

Ph:

Phenyl

Pr:

Propyl

Pv:

Pivaloyl

py:

Pyridine

rt:

Room temperature

SFC:

Solvent free condition

SPS:

Solid-phase synthesis

TBAF:

Tetrabutylammonium fluoride

t-Bu:

Tert-butyl

Tf:

Trifluoromethanesulfonyl (triflyl)

THF:

Tetrahydrofuran

THP:

Tetrahydropyran-2-yl

TMS:

Trimethylsilyl

Tp:

Tetrazole

Ts:

Tosyl 4-toluenesulfonyl

XRD:

X-ray diffraction

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Authors and Affiliations

  1. Ural Federal University, Mira Str. 19, Yekaterinburg, 620002, Russia

    Nataliya Belskaya, Julia Subbotina & Svetlana Lesogorova

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  1. Nataliya Belskaya
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  2. Julia Subbotina
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  3. Svetlana Lesogorova
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Correspondence to Nataliya Belskaya .

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  1. Department of Chemistry, KU Leuven, Leuven, Belgium

    Wim Dehaen

  2. Ural Federal University, Yekaterinburg, Russia

    Vasiliy A. Bakulev

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Belskaya, N., Subbotina, J., Lesogorova, S. (2014). Synthesis of 2H-1,2,3-Triazoles. In: Dehaen, W., Bakulev, V. (eds) Chemistry of 1,2,3-triazoles. Topics in Heterocyclic Chemistry, vol 40. Springer, Cham. https://doi.org/10.1007/7081_2014_125

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