Amides as precursors of imidoyl radicals in cyclisation reactions

被引：31

作者：

Bowman, W. Russell ^{[1
]}

Fletcher, Anthony J.

Pedersen, Jan M.

Lovell, Peter J.

Elsegood, Mark R. J.

Lopez, Elena Hernandez

McKee, Vickie

Potts, Graeme B. S.

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] GlaxoSmithKline, Psychiat Med Chem 2, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON | 2007年 / 63卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

imidoyl radicals; radical cyclisation; imidoyl selanides; indoles; quinolines;

D O I：

10.1016/j.tet.2006.10.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：191 / 203

页数：13

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