Efficacious and rapid metal- and solvent-free synthesis of enantiopure oxazolines

Hassani, Rym; Requet, Alexandre; Marque, Sylvain R. A.; Gaucher, Anne; Prim, Damien; Kacem, Yakdhane; Hassine, Béchir Ben

doi:10.1016/j.tetasy.2014.08.010

Cited by 15 publications

(5 citation statements)

References 43 publications

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“…14 It can also be synthesized under microwave irradiation with a higher temperature. 15 For the sake of easy workup, we carried out this transformation with the modified Witte−Seeliger reaction in a sealed tube at 150 °C catalyzed by freshly flame-dried ZnCl 2 under solventfree conditions. The amide bond formation was realized in Antifungal Activity and SAR Discussion.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The chiral oxazoline units were established by condensation of commercially available aromatic nitrile and different amino alcohols based on the ZnCl 2 -catalyzed Witte–Seeliger reaction . It can also be synthesized under microwave irradiation with a higher temperature . For the sake of easy workup, we carried out this transformation with the modified Witte–Seeliger reaction in a sealed tube at 150 °C catalyzed by freshly flame-dried ZnCl 2 under solvent-free conditions.…”

Section: Resultsmentioning

confidence: 99%

“…There was a tiny modification from the literature report procedure. 15 To an oven-dried tube under a nitrogen atomosphere was added 2-aminobenzonitrile (118 mg, 1 mmol), (R)-2-aminopropan-1ol, and freshly flame-dried ZnCl 2 (13 mg, 10% mmol). The mixture was sealed with Teflon tape and stirred at 150 °C, and the reaction progress was monitored by TLC until the consumption of aminobenzonitrile (6−8 h).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…There was a tiny modification from the literature report procedure . To an oven-dried tube under a nitrogen atomosphere was added 2-aminobenzonitrile (118 mg, 1 mmol), ( R )-2-aminopropan-1-ol, and freshly flame-dried ZnCl 2 (13 mg, 10% mmol).…”

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Xiao

et al. 2016

J. Agric. Food Chem.

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Chirality greatly influences the biological and pharmacological properties of a pesticide and will contribute to unnecessary environmental loading and undesired ecological impact. No structure and activity relationship (SAR) of enantiopure succinate dehydrogenase inhibitors (SDHIs) was documented during the structure optimization of boscalids. On the basis of commercial SDHIs, oxazoline natural products, and versatile oxazoline ligands in organic synthesis, the first effort was devoted to explore the chiral SDHIs and the preliminary mechanism thereof. Fine-tuning furnished chiral nicotinamides 4ag as a more promising fungicidal candidate against Rhizoctonia solani, Botrytis cinerea, and Sclerotinia sclerotiorum, with EC values of 0.58, 0.42, and 2.10 mg/L, respectively. In vivo bioassay and molecular docking were investigated to explore the potential in practical application and plausible novelty in action mechanism, respectively. The unexpected molecular docking model showed the different chiral effects on the binding site with the amino acid residues. This chiral nicotinamide also featured easy synthesis and cost-efficacy. It will provide a powerful complement to the commercial SDHI fungicides with the introduction of chirality.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Xiao

et al. 2016

J. Agric. Food Chem.

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“…The ligands bis- and mono-oxazolines were prepared from the available optically pure α-aminoalcohols (derived from the corresponding amino acids). ( S )-4-Isopropyl-2-(naphthalen-1-yl)oxazoline ( 2 ) was isolated in a moderate yield from the condensation of the L-valinol with naphthonitrile under microwave irradiation, while the second ligand 1,2-bis[( S )-4-phenyloxazoline]benzene ( 7 ) was synthesized from L-(α)-(+)-phenylglycinol under the same conditions of the reaction as described by B. Ben Hassine et al [ 42 ]. The third ligand 3-[(4 S )-4,5-dihydro-4-isopropyl-1,3-oxazol-2-yl]propanenitrile ( 11 ) was obtained using the reaction of 4-ethoxy-4-iminobutanenitrile monohydrochloride with L-valinol in high yield [ 43 ].…”

Section: Methodsmentioning

confidence: 99%

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

Hassani

Jabli

Kacem

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe present paper describes the synthesis of new palladium–oxazoline complexes in one step with good to high yields (68–95%). The oxazolines were prepared from enantiomerically pure α-aminoalcohols. The structures of the synthesized palladium complexes were confirmed by NMR, FTIR, TOFMS, UV–visible spectroscopic analysis and X–ray diffraction. The optical properties of the complexes were evaluated by the determination of the gap energy values (E g) ranging between 2.34 and 3.21 eV. Their catalytic activities were tested for the degradation of Eriochrome Blue Black B (a model of azo dyes) in the presence of an ecological oxidant (H2O2). The efficiency of the decolorization has been confirmed via UV–visible spectroscopic analysis and the factors affecting the degradation phenomenon have been studied. The removal of the Eriochrome reached high yields. We have found that the complex 9 promoted 84% of color elimination within 5 min (C 0 = 30 mg/L, T = 22 °C, pH 7, H2O2 = 0.5 mL) and the energetic parameters have been also determined.

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ChemInform Abstract: Efficacious and Rapid Metal‐ and Solvent‐Free Synthesis of Enantiopure Oxazolines.

et al. 2015

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Efficacious and Rapid Metal-and Solvent-Free Synthesis of Enantiopure Oxazolines. -The enantiopure oxazolines are synthesized without using any catalysts and solvents from various nitriles and enantiopure amino alcohols under microwave irradiation at high temperature (150 to 240 C) in short reaction time (60 to 100 min). -(HASSANI, R.; REQUET, A.; MARQUE, S.; GAUCHER, A.; PRIM, D.; KACEM, Y.; HASSINE*, B.

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Efficacious and rapid metal- and solvent-free synthesis of enantiopure oxazolines

Cited by 15 publications

References 43 publications

Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

ChemInform Abstract: Efficacious and Rapid Metal‐ and Solvent‐Free Synthesis of Enantiopure Oxazolines.

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