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

被引:21
作者
Piccionello, Antonio Palumbo [1 ]
Pace, Andrea [1 ]
Buscemi, Silvestre [1 ]
Vivona, Nicolo [1 ]
Pani, Marcella [2 ]
机构
[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy
[2] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
关键词
1,2,4-oxadiazole; Montmorillonite; imidazoles; beta-dicarbonyls; beta-enaminoketones; crystal structure;
D O I
10.1016/j.tet.2008.02.047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated beta-dicarbonyl compounds and subsequent base-induced Boulton-Katritzky Rearrangement (BKR) of the isolated beta-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. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4004 / 4010
页数:7
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