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Article Dans Une Revue Tetrahedron Année : 2008

Solvent-free synthesis of nitrones in a ball-mill

Résumé

Various C-aryl and C-alkyl-nitrones were synthesized within 0.5-2h via condensation of an equinolear amount of aldehydes and N-substituted-hydroxylamines under solvent free conditions in a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C Mass nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed be superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN).
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Dates et versions

hal-00278417 , version 1 (01-02-2021)

Identifiants

Citer

Evelina Colacino, Pierrick Nun, Francesco Maria Colacino, Jean Martinez, Frédéric Lamaty. Solvent-free synthesis of nitrones in a ball-mill. Tetrahedron, 2008, 64, pp.5569-5576. ⟨10.1016/j.tet.2008.03.091⟩. ⟨hal-00278417⟩
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