Green catalytic synthesis of symmetric and non-symmetric β-hydroxy-1,2,3-triazoles by using epichlorohydrin in the presence of Cu(<scp>ii</scp>) coordination compounds containing oxazole ligands

Ajormal, Fatemeh; Bikas, Rahman; Noshiranzadeh, Nader; Kozakiewicz, Anna; Lis, Tadeusz

doi:10.1039/d2nj03826a

Cited by 7 publications

(5 citation statements)

References 91 publications

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“…It should be noted that the selective formation of Schiff base depends on the reaction temperature and also the ratio of reagents. According to our previous reports 1,3-oxazolidine 56 or bis-oxazole 57 ligands can be obtained at higher temperatures by further reaction of one or both of the alcoholic arms, respectively. The results of 1 H NMR, 13 C NMR, UV–Vis, and FT-IR spectra confirmed the successful synthesis of the ligand.…”

Section: Resultsmentioning

confidence: 86%

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

Ajormal,

Bikas,

Noshiranzadeh

et al. 2024

Sci Rep

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A pro-chiral Schiff base ligand (HL) was synthesized by the reaction of 2-amino-2-ethyl-1,3-propanediol and pyridine-2-carbaldehyde in methanol. The reaction of HL with CuCl2·2H2O and CuBr2 in methanol gave neutral mononuclear Cu(II) complexes with general formula of [Cu(HL)Cl2] (1) and [Cu(HL)Br2] (2), respectively. By slow evaporation of the methanolic solutions of 1 and 2, their enantiomers were isolated in crystalline format. The formation of pure chiral crystals in the racemic mixture was amply authenticated by single crystal X-ray analysis, which indicated that S-[Cu(HL)Cl2], R-[Cu(HL)Cl2], and S-[Cu(HL)Br2] are crystallized in chiral P212121 space group of orthorhombic system. Preferential crystallization was used to isolate the R and S enantiomers as single crystals and the isolated compounds were also studied by CD analysis. Structural studies indicated that the origin of the chirality in these compounds is related to the coordination mode of the employed pro-chiral ligand (HL) because one of its carbon atoms has been converted to a chiral center in the synthesized complexes. Subsequently, these complexes were used in click synthesis of a β-hydroxy-1,2,3-triazole and the results of catalytic studies indicated that 1 and 2 can act as enantioselective catalysts for the asymmetric synthesis of β-hydroxy-1,2,3-triazole product under mild condition. This study illustrates the significant capacity of the use of pro-chiral ligands in preparing chiral catalysts based on complexes which can also be considered as an effective approach to cheap chiral catalysts from achiral reagents.

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Section: Resultsmentioning

confidence: 86%

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

Ajormal,

Bikas,

Noshiranzadeh

et al. 2024

Sci Rep

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“…The Cu–N and Cu–O distances are in the normal range observed in previously reported Cu( ii )-hydrazones. 32 The bond lengths of C8–O1 and N2–C8 indicate that the hydrazone ligand is connected to the copper( ii ) core in the amidic form and the ligand acts as a mononegative tridentate ONO-donor ligand due to elimination of the phenolic hydrogen atom in the structure of 1 . An uncoordinated CH 3 OH molecule is located in the crystal lattice of 1 , which is stabilized in the crystal by hydrogen bond interactions (see dashed pink lines in Fig.…”

Section: Resultsmentioning

confidence: 99%

Green carbon–carbon homocoupling of terminal alkynes by a silica supported Cu(ii)-hydrazone coordination compound

et al. 2023

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“…Notably, water was the only by-product, offering a green and practical synthetic method for 1,4-disubstituted 1,2,3-triazole. Ajormal 138 The resulting compounds were utilized as catalysts for the eco-friendly synthesis of symmetric and non-symmetric 1,4-disubstituted 1,2,3-triazoles involving azide-phenylacetylene-epichlorohydrin cycloaddition reaction under mild and green reaction conditions in water as a solvent, as depicted in Table 4, entry (12).…”

Section: Entrymentioning

confidence: 99%

Green synthesis of 1,4-disubstituted 1,2,3-triazoles: a sustainable approach

Kumar,

Lal,

Tittal

2024

Green Chem.

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Green catalytic synthesis of symmetric and non-symmetric β-hydroxy-1,2,3-triazoles by using epichlorohydrin in the presence of Cu(ii) coordination compounds containing oxazole ligands

Abstract: Three Cu(II) coordination compounds, [Cu(L1)(Cl2)] (1), [Cu(L1)(Br2)] (2), and [Cu(L2)(Cl)]Cl∙(C2H4O3)0.5(H2O)0.5 (3), were synthesized and characterized by various spectroscopic methods and single crystal X-ray analysis where L1 and L2 are oxazolo[3,4-c]...

Cited by 7 publications

References 91 publications

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

Green carbon–carbon homocoupling of terminal alkynes by a silica supported Cu(ii)-hydrazone coordination compound

Green synthesis of 1,4-disubstituted 1,2,3-triazoles: a sustainable approach

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