Reaction of N‐(phenyl and methyl)‐C‐arylnitrones with DMAD in ionic liquid: Efficient synthesis of Δ4‐isoxazolines |
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| Authors: | Hassan Valizadeh Esmail Vesally Leila Dinparast |
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| Affiliation: | 1. Department of Chemistry, Islamic Azad University, Myianeh Branch, Myianeh, Iran;2. Payame Noor University (PNU), Zanjan, Iran;3. Department of Chemistry, Faculty of Science, Azarbaijan University of Tarbiat Moallem, P. O. Box 53714‐161, Tabriz, Iran |
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| Abstract: | Facile synthesis of N‐(methyl and phenyl)‐Δ4‐isoxazolines via the reaction of (Z)‐N‐(methyl and phenyl)‐C‐arylnitrones with dimethyl acethylenedicarboxylate, DMAD, in ionic liquid is described. (Z)‐N‐methyl‐C‐arylnitrones afforded the high yield of N‐methyl‐Δ4‐isoxazolines 4a , 4b , 4c , 4d , 4e in ionic liquid, [bmim]BF4, at room temperature. However, the reaction of (Z)‐N‐phenyl‐C‐arylnitrones with DMAD afforded the mixtures of cis and trans isomers of related N‐phenyl‐Δ4‐isoxazolines ( 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j , 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j ) under these conditions. J. Heterocyclic Chem., (2012). |
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