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

来源：

TETRAHEDRON | 2008年 / 64卷 / 18期

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.

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页码：4004 / 4010

页数：7

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