Tetrahedron

Synthesis of trifluoromethylated 2-benzoyl-and 2-aminoimidazoles from ring rearrangement of 1, 2, 4-oxadiazole derivatives

AP Piccionello, A Pace, S Buscemi, N Vivona, M Pani

Index: Palumbo Piccionello, Antonio; Pace, Andrea; Buscemi, Silvestre; Vivona, Nicolo; Pani, Marcella Tetrahedron, 2008 , vol. 64, # 18 p. 4004 - 4010

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Citation Number: 26

Abstract

Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5- phenyl-1, 2, 4-oxadiazole with fluorinated β-dicarbonyl compounds and subsequent base- induced Boulton–Katritzky Rearrangement (BKR) of the isolated β-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 ...