Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I).: A comparison of cyclisation methods

被引:68
作者
Davies, DT
Kapur, N
Parsons, AF [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] SmithKline Beecham Pharmaceut, Dept Med Chem, Harlow CM19 5AW, Essex, England
关键词
manganese and compounds; copper and compounds; cyclisation; enamides;
D O I
10.1016/S0040-4020(00)00316-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo-trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3941 / 3949
页数:9
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