Generation of new fluorophore by Click chemistry: synthesis and properties of β-cyclodextrin substituted by 2-pyridyl triazole

David, Olivier; Maisonneuve, Stéphane; Xie, Juan

doi:10.1016/j.tetlet.2007.07.071

Cited by 113 publications

(58 citation statements)

References 31 publications

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“…It is interesting to emphasize here that despite the dramatic upturn in usage of click chemistry over the last few years, applications to prepare azacrown macrocycle derivatives remain scarce. [26] This is rather surprising since the formed 1,4-disubstituted 1,2,3-triazole shares sim- [27] complexes with copper, [15,[28][29][30][31] zinc, [30][31][32][33] nickel, [31] silver, [28,34] iron, [33,35,36] ruthenium, [33,35,37] or palladium [38] have been reported, for instance. Recently, we published the synthesis of the L1 ligand and the characterization of its complex with Cu 2+ , which, to the best of our knowledge, was the first solid-state structural study of a copper complex that involved coordinated diaza [18]crown-6 and 1,2,3-triazolyl ligands.…”

Section: +mentioning

confidence: 99%

Evolution of the Coordination‐Sphere Symmetry in Copper(II), Nickel(II), and Zinc(II) Complexes with N,N′‐Double‐Armed Diaza‐Crown Ethers: Experimental and Theoretical Approaches

et al. 2014

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crown-6 ligand were determined by means of X-ray crystallography. The Ni II complex is centrosymmetric; the geometry around the metal ion is slightly distorted octahedral whereby the equatorial sites were occupied by four N atoms, and the axial positions by two O atoms that come from the crown moiety. For the Zn IIdiaza[18]crown-6 complex, an irregular octahedral coordination was observed whereby the metal ion is asymmetrically placed in the macrocyclic cavity. The equatorial plane is occupied by two N and two O atoms of the crown moiety, and two N atoms of the triazolyl motifs on the pendant arms occupy the axial positions. The diamagnetic character of the Zn II ion allows its structural study in solution by NMR spectroscopy. A dynamic behavior was observed at room tem-

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Section: +mentioning

confidence: 99%

Evolution of the Coordination‐Sphere Symmetry in Copper(II), Nickel(II), and Zinc(II) Complexes with N,N′‐Double‐Armed Diaza‐Crown Ethers: Experimental and Theoretical Approaches

et al. 2014

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“…R f = 0. 48 The reaction was heated to reflux overnight, then the solvent was removed under reduced pressure and the residue was purified as indicated below.…”

Section: Heptakis(6-o-tert-butyldimethylsilyl-23-di-o-propargyl)cyclmentioning

confidence: 99%

“…The copper(I)-mediated Huisgen 1,3-dipolar cycloaddition came to our attention because this reaction meets both criteria. The reaction has been successfully applied to CD chemistry by introducing functional groups to the primary face, [43][44][45][46][47][48] but its use to introduce functional groups to the secondary face has been demonstrated only in a limited number of cases. For example, in 2007, Santoyo-Gonzaley's group used a per-3-O-propargylated β-CD to prepare a per-3-O-substituted glycocluster.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

Ward

Ling

2011

Eur J Org Chem

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The perfunctionalization of the secondary face of cyclodextrins (CDs) is a challenging task that often results in poor yields. Here, we report that the use of copper‐catalyzedHuisgen 1,3‐dipolar cycloaddition is an efficient and versatile strategy that provides perfunctionalized CDs at the secondary face with good to high yields. A variety of functional groups, such as alkyl, alkenyl, ester, carboxylic acid, amide, and alcohol, have been successfully incorporated on the secondary face of β‐CD from the same starting material. These functionalized CD derivatives could be used as building blocks for further structural modification or as hosts for different applications.

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“…Moreover, their derivatives find industrial applications as flurophores, chemosensors, and charge-transfer agents [9][10][11]. Thienopyrimidones have continued to retain attention of both academic institutions and pharmaceutical companies in the last few years [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry Based Synthesis of Novel Architectures Bearing Sugar Unit at the Pyridothienopyrimidines

Ameen

Ahmed

Malah

et al. 2014

Journal of Heterocyclic Chem

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Novel conjugates of pyridothienopyrimidinones and carbohydrates or other moieties linked by 1,2,3‐triazoles were synthesized. After establishing the pyridothienopyrimidone ring systems by ring closure, propargyl group was introduced by O‐alkylation or N‐alkylation. Cu‐catalyzed cycloaddition of the propargyl product with azido group gave the corresponding 1,2,3‐triazoles in high yields. A remarkable case of the catalyzed ring closure to build a pyrimidinone moiety with two diastereomers was observed. Theoretical calculations were performed on the studied diastereomers, and it was found that the S‐isomer is more stable than the corresponding R‐isomer by about 2 kcal/mol.

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Generation of new fluorophore by Click chemistry: synthesis and properties of β-cyclodextrin substituted by 2-pyridyl triazole

Cited by 113 publications

References 31 publications

Evolution of the Coordination‐Sphere Symmetry in Copper(II), Nickel(II), and Zinc(II) Complexes with N,N′‐Double‐Armed Diaza‐Crown Ethers: Experimental and Theoretical Approaches

Evolution of the Coordination‐Sphere Symmetry in Copper(II), Nickel(II), and Zinc(II) Complexes with N,N′‐Double‐Armed Diaza‐Crown Ethers: Experimental and Theoretical Approaches

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

Click Chemistry Based Synthesis of Novel Architectures Bearing Sugar Unit at the Pyridothienopyrimidines

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