Reactivity of N-(ω-haloalkyl)-β-lactams with regard to lithium aluminium hydride:: novel synthesis of 1-(1-aryl-3-hydroxypropyl)aziridines and 3-aryl-3-(N-propylamino)propan-1-ols

被引：14
作者：
D'hooghe, Matthias [1 ]
Dekeukeleire, Stijn [1 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 07期
关键词：
D O I：
10.1039/b719686e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactivity of 4-aryl-1-(2-chloroethyl)azetidin-2-ones and 4-aryl-1-(3-bromopropyl)azetidin-2-ones with regard to lithium aluminium hydride has been evaluated for the first time. 4-Aryl-1-(2-chloroethyl)azetidin-2-ones were transformed into novel 1-(1-aryl-3-hydroxypropyl)aziridines through an unprecedented conversion of beta-lactams into 2,3-unsubstituted aziridine derivatives. Unexpectedly, 4-aryl-1-(3-bromopropyl)azetidin-2-ones underwent dehalogenation towards 3-aryl-3-(N-propylamino)propan-1-ols upon treatment with LiAlH4. 1-(1-Aryl-3-hydroxypropyl)aziridines were further elaborated by means of ring opening reactions using benzyl bromide in acetonitrile towards 3-aryl-3-[N-benzyl-N-(2-bromoethyl)amino]propan-1-ols and using aluminium(III) chloride in diethyl ether, affording 3-aryl-3-[N-(2-chloroethyl)amino]propan-1-ols.
引用
收藏
页码：1190 / 1196
页数：7
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