Intramolecular addition of benzylic radicals onto ketenimines.: Synthesis of 2-alkylindoles

被引:45
作者
Alajarín, M [1 ]
Vidal, A [1 ]
Ortín, MM [1 ]
机构
[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain
关键词
D O I
10.1039/b310593h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The inter- and intramolecular addition of free radicals onto ketenimines is studied. All the attempts to add intermolecularly several silicon, oxygen or carbon centered radicals to N-(4-methylphenyl)- C, C-diphenyl ketenimine were unsuccessful. In contrast, the intramolecular addition of benzylic radicals, generated from xanthates, onto the central carbon of a ketenimine function with its N atom linked to the ortho position of the aromatic ring occurred under a variety of reaction conditions. These intramolecular cyclizations provide a novel radical-mediated synthesis of 2-alkylindoles.
引用
收藏
页码:4282 / 4292
页数:11
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