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

TETRAHEDRON LETTERS

卷:56

Article

Nambu, Hisanori¹  Fukumoto, Masahiro¹  Hirota, Wataru¹  Ono, Naoki¹  Yakura, Takayuki¹ 

[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

关键词: Cyclopropane;    1,3-Cyclohexanediones;    Sulfonium salts;    Indole;    One-pot synthesis;   

DOI  :  10.1016/j.tetlet.2015.05.069

来源: Elsevier

【 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.

【 授权许可】

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