Palladium-catalyzed Cycloaddition of Aryl Silylethynyl Ethers with Isocyanates via o-C-H Cleavage

被引：11
|
作者：
Minami, Yasunori [1 ,2 ]
Kanda, Mayuko [3 ]
Hiyama, Tamejiro [1 ,2 ]
机构：
[1] Chuo Univ, Res & Dev Initiat, Bunkyo Ku, Tokyo 1128551, Japan
[2] JST, ACT C, Chiyoda Ku, Tokyo 1020076, Japan
[3] Chuo Univ, Dept Appl Chem, Bunkyo Ku, Tokyo 1128551, Japan
来源：
CHEMISTRY LETTERS | 2014年 / 43卷 / 09期
关键词：
ONE-POT SYNTHESIS; BOND ACTIVATION; AMIDATION; MOLECULES; INSERTION; 2H-1,4-BENZOXAZIN-3-(4H)-ONES; HYDROARYLATION; CARBOACYLATION; ANNULATION; OLEFINS;
D O I：
10.1246/cl.140452
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Palladium-catalyzed cycloaddition of alkynyl aryl ethers with isocyanates proceeds through o-C-H activation to afford 2-methylidene-2H-1,4-benzoxazin-3(4H)-one derivatives. Deuterium-labeling experiment shows that o-hydrogen is cleaved selectively and migrated to 2-methylidene moiety in the product. Various substrates are applied to this transformation to afford various substituted cycloadducts. 1,4-Bis(alkynoxy)benzenes can be used for the synthesis of multicondensed cycles to afford benzo [1,2-b:4,5-b']bis[1,4]oxazine-3,8-dione derivatives.
引用
收藏
页码：1408 / 1410
页数：3
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