Dinuclear oxidovanadium complexes with dihydrazone ligands derived from diethyl 2,6-dimethylpyridine-3,5-dicarboxylate obtained from Hantzsch reaction; crystal structure and catalytic activity

Soltani, Fatemeh; Bikas, Rahman; Heydari, Neda; Kozakiewicz, Anna

doi:10.1039/d2nj06279h

Cited by 5 publications

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References 110 publications

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“…In the infrared spectrum of HL (Fig. S1 ), the broad characteristic band at 3455 cm −1 can be assigned to the –OH groups of the two alcoholic arms 58 – 60 . The imine bond vibration (υC=N) is observed as a strong band at 1657 cm −1 which confirms the successful formation of the Schiff base ligand 61 – 63 In the 1 H NMR spectrum of HL (see Fig.…”

Section: Resultsmentioning

confidence: 99%

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: 99%

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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Catalytic Oxidation of Aliphatic Alcohols by Graphene Oxide Supported Binuclear Dioxidovanadium (V) Complexes

Kachhap,

Chaudhary,

Haldar

2023

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Synthesis, crystal structures, photophysical and antibacterial properties of Ag(I) and Zn(II) coordination polymers based on a flexible bisacylhydrazone ligand

et al. 2023

Inorganica Chimica Acta

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Dinuclear oxidovanadium complexes with dihydrazone ligands derived from diethyl 2,6-dimethylpyridine-3,5-dicarboxylate obtained from Hantzsch reaction; crystal structure and catalytic activity

Abstract: The Two new dihydrazone ligands (H4L1 and H4L2) have been prepared from Hantzsch pyridine ester and after characterization by analytical methods; they have been used in the synthesis of oxidovanadium...

Cited by 5 publications

References 110 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

Catalytic Oxidation of Aliphatic Alcohols by Graphene Oxide Supported Binuclear Dioxidovanadium (V) Complexes

Synthesis, crystal structures, photophysical and antibacterial properties of Ag(I) and Zn(II) coordination polymers based on a flexible bisacylhydrazone ligand

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