Synthesis of α-Chlorolactams by Cyanoborohydride-Mediated Radical Cyclization of Trichloroacetamides

被引：6

作者：

Coussanes, Guilhem ^{[1
]}

Jakobi, Harald ^{[2
]}

Lindell, Stephen ^{[2
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, IBUB, Lab Quim Organ, Av Joan 23 S-N, E-08028 Barcelona, Spain

[2] Bayer AG, Crop Sci Div, Ind Pk Hochst G836, D-65926 Frankfurt, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 32期

关键词：

borohydrides; herbicides; lactams; radical cyclizations; synthetic methods; SODIUM-BOROHYDRIDE; STANNYLATED POLYNORBORNENES; NONREDUCTIVE ALKYLATION; GAMMA-LACTAMS; ACETIC-ACID; HALIDES; KETONES; HYDRIDE; SUBSTITUENT; REDUCTIONS;

D O I：

10.1002/chem.201800210

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cyanoborohydride-promoted radical cyclization methodology has been developed to access -chlorolactams in a simple and efficient way using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of alpha-chlorolactams (mono- and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.

引用

收藏

页码：8151 / 8156

页数：6

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