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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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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