Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated b-dicarbonyl compounds and subsequent base-induced BoultoneKatritzky Rearrangement (BKR) of the isolated b-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.
PALUMBO PICCIONELLO A, PACE A, BUSCEMI S, VIVONA N, PANI M (2008). Synthesis of trifluoromethylated 2-benzoyl- and 3-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivative. TETRAHEDRON, 64, 4004-4010 [10.1016/j.tet.2008.02.047].
Synthesis of trifluoromethylated 2-benzoyl- and 3-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivative
PALUMBO PICCIONELLO, Antonio;PACE, Andrea;BUSCEMI, Silvestre;VIVONA, Nicolo';
2008-01-01
Abstract
Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated b-dicarbonyl compounds and subsequent base-induced BoultoneKatritzky Rearrangement (BKR) of the isolated b-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.File | Dimensione | Formato | |
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