An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: application to a one-pot synthesis of tetrahydroindol-4(5H)-one

被引：27
|
作者：
Nambu, Hisanori [1 ]
Fukumoto, Masahiro [1 ]
Hirota, Wataru [1 ]
Ono, Naoki [1 ]
Yakura, Takayuki [1 ]
机构：
[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 29期
关键词：
Cyclopropane; 1,3-Cyclohexanediones; Sulfonium salts; Indole; One-pot synthesis; RHODIUM-CATALYZED CYCLOPROPANATION; SUBSTITUTED VINYLSULFONIUM SALTS; BROMODIMETHYLSULFONIUM BROMIDE; ASYMMETRIC CYCLOPROPANATION; ACTIVATED CYCLOPROPANES; ALKENES; REAGENTS; ROUTE; CYCLOADDITION; DIHYDROFURANS;
D O I：
10.1016/j.tetlet.2015.05.069
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of cyclohexane- and cyclopentane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using sulfonium salts was achieved. The reaction of 1,3-cycloalkanediones with (1-aryl-2-bromoethyl)-dimethylsulfonium bromides and powdered K2CO3 in EtOAc provided the corresponding spirocyclopropanes in high yields. Furthermore, a one-pot synthesis of tetrahydroindol-4(5H)-one from 1,3-cyclohexanedione was achieved using the present protocol and a sequential ring-opening cyclization of spirocyclopropane with a primary amine. (c) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4312 / 4315
页数：4
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