An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)-diphenylsulfonium Trifluoromethanesulfonate

被引:21
作者
Nambu, Hisanori [1 ]
Ono, Naoki [1 ]
Hirota, Wataru [1 ]
Fukumoto, Masahiro [1 ]
Yakura, Takayuki [1 ]
机构
[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
基金
日本学术振兴会;
关键词
cyclopropane; sulfonium salt; spiro compound; 1,3-cyclohexanedione; double alkylation; RING-OPENING CYCLIZATION; VINYL SULFONIUM SALTS; ACCEPTOR; CYCLOPROPANES; CASCADE; ACID;
D O I
10.1248/cpb.c16-00625
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient and practical synthesis of 2',3'-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.
引用
收藏
页码:1763 / 1768
页数:6
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