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Volume 22, Issue 1
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

Abstract

Some new ()-2-[1-aryl-5-methyl-1-1,2,3-triazol-4-yl]-4-benzyl-4,5-dihydro-oxazoline were synthesized by the reaction of ()--(1-hydroxy-3-phenylpropan-2-yl)-1-aryl-5-methyl-1-1,2,3-triazole-4-carboxamides which were prepared from aromatic amine as starting materials, with -toluenesulfonyl chloride, triethylamine and DMAP. The structures were characterized by 1H NMR, 13C NMR, MS and IR. The synthesized chiral triazole-oxazoline was used as a ligand in the Diels-Alder asymmetric catalytic reaction between 3-allyl-1,3-oxazolidin-2-ketone and 2-methyl-1,3-butadiene, using PdCl as catalyst. ()-3-(4-methylcyclohexe-3-ene-1-formyl)-1,3-oxazolidin-2-one was obtained.

Background

The chiral triazole-oxazoline ligands are rarely reported.

Objective

The aim of the study was to synthsize some new chiral triazole-oxazoline ligands ()-4-benzyl-2-(1-aryl-5-methyl-1-1,2,3-triazole-4-yl)-4,5-dihydrooxazoline ().

Methods

The one-pot methods of oriented synthesis were adopted. This study provides a simple and effective method for the synthesis of new chiral triazole-oxazoline derivatives.

Results

The some new chiral the triazole-oxazoline ligands ()-4-benzyl-2-(1-aryl-5-methyl-1-1,2,3-triazole-4-yl)-4,5-dihydrooxazoline () were synthesized and the asymmetric Diels-Alder cyclization of 3-allyl-1,3-oxazolidin-2-ketone and 2-methyl-1,3-butadiene was catalyzed by PdCl using the synthesized ()-4-triazole-oxazoline ligands.

Conclusion

Some new ()-4-benzyl-2-(1-aryl-5-methyl-1-1,2,3-triazole-4-yl)-4,5-dihydro-oxazoline was synthesized by corresponding -[(S)-1-hydroxy-3-phenylpropan-2-yl]-1-aryl-5-methyl-1-1,2,3-triazole-4-formamide, through one-pot oriented synthesis method. After preliminary evaluation, the chiral triazoline-oxazoline ligands, in which 1,2,3-triazole rings, like pyridine-type rings, chiral materials were saved and replace one oxazoline ring in the dioxazoline ligands for asymmetric catalytic reactions.

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2024-07-11
2025-05-09

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Synthesis of Some New Chiral Triazole-oxazoline Derivatives
Curr. Org. Synth. 22, 136 (2025); https://doi.org/10.2174/0115701794317332240610073030
/content/journals/cos/10.2174/0115701794317332240610073030
/content/journals/cos/10.2174/0115701794317332240610073030
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The preparation experiment details of the compound, the main raw material identifier (CAS Registry Number), the spectral data of some raw material compounds, and the 1H NMR and 13C NMR nuclear magnetic spectra of the new compound are displayed in the auxiliary materials. These materials can be downloaded from our website (https://www.eurekaselect.com/journal/cos.doi.10.2174/0115701794317332240610073030 ).

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  • Article Type:     Research Article
Keyword(s): 1H-1,2,3-triazole; 4,5-dihydro-oxazoline; aromatic amine; chirality; synthesis; triazole-oxazoline

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