Synthesis of optically active 1-(1-phenylethyl)-1H-imidazoles derived from 1-phenylethylamine

被引：17
|
作者：
Mloston, Grzegorz [1 ]
Mucha, Paulina [1 ]
Urbaniak, Katarzyna [1 ]
Broda, Karolina [1 ]
Heirngartner, Heinz [2 ]
机构：
[1] Univ Lodz, Dept Organ & Appl Chem, PL-90136 Lodz, Poland
[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
来源：
HELVETICA CHIMICA ACTA | 2008年 / 91卷 / 02期
关键词：
D O I：
10.1002/hlca.200890028
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The three-component reaction of (R)- or (S)-1-phenylethylamine (6), formaldehyde, and an alpha-(hydroxyimino) ketone 5, i.e., 3-(hydroxyimino)butan-2-one (5a) or 2-(hydroxyimino)-1,2-diphenylethanone (5b), yields the corresponding enantiomerically pure 1-(1-phenylethyl) -1H-imidazole 3-oxide 7 in high yield (Schemes 2 and 3). The reactions are carried out either in MeOH or in AcOH. Smooth transformations of the N-oxides into optically active 1-(1-phenylethyl)-1H-imidazoles 10 and 2,3-dihydro-1 -(1-phenylethyl)-1H-imidazole-2-thiones 11 are achieved by treatment of 7 with Raney-Ni and 2,2,4,4-tetramethyl-3-thioxocyclobutanone (12), respectively (Scheme 4).
引用
收藏
页码：232 / 238
页数：7
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