Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation

被引：21
|
作者：
Quideau, S [1 ]
Pouységu, L [1 ]
Avellan, AV [1 ]
Whelligan, DK [1 ]
Looney, MA [1 ]
机构：
[1] Univ Bordeaux 1, Ctr Rech Chim Mol, Lab Chim Subst Vegetales, F-33405 Talence, France
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 42期
关键词：
hypervalent iodine; arene chemistry; oxidative activation; orthoquinol acetate; heterocyclization;
D O I：
10.1016/S0040-4039(01)01514-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride- or base-induce intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this methodology for the synthesis or a functionalized lycorine-type alkaloid skeleton is introduced here. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7393 / 7396
页数：4
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