A new synthesis of 2-methyleneaziridines

被引:58
作者
DeKimpe, N
DeSmaele, D
Sakonyi, Z
机构
[1] Department of Organic Chemistry, Fac. of Agric./Appl. Biol. Sciences, University of Gent, B-9000 Gent
[2] A. Szent Gyorgyi Medical University, Szeged
关键词
2-(BROMOMETHYL)AZIRIDINES;
D O I
10.1021/jo962351v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of beta-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoaze-tidines, through ring expansion with azides carrying electron-withdrawing substituents.
引用
收藏
页码:2448 / 2452
页数:5
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