Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles

被引：75
|
作者：
Thansandote, Praew [1 ]
Hulcoop, David G. [1 ]
Langer, Michael [1 ]
Lautens, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期
基金：
加拿大自然科学与工程研究理事会;
关键词：
MARINE NATURAL-PRODUCTS; DIELS-ALDER; DERIVATIVES; ALKALOIDS; SUBSTITUTION; ALKYLATION; ARYLATION; AMINES; LEADS;
D O I：
10.1021/jo802604g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.
引用
收藏
页码：1673 / 1678
页数：6
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