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

页码：4312 / 4315

页数：4

共 50 条

[41] SbCl5.SiO2: an efficient alternative for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles in solvent or under solvent-free condition
B. Sadeghi
B. B. F. Mirjalili
S. Bidaki
M. Ghasemkhani
Journal of the Iranian Chemical Society, 2011, 8 : 648 - 652
[42] One-pot synthesis of novel symmetric 1,5-di(benzofuran-2-yl)-3-(4-substituted-aryl)-pentane-1,5-dione derivatives
Kumar, Aruna D. B.
Desai, Nivedita R.
Krishnaswamy, G.
Sreenivasa, S.
Mahadevan, K. M.
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (04): : 426 - 430
[43] Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3
Suo Juan Wu
Zi Qiang Zhao
Jing Shuo Gao
Bao Hua Chen
Guo Feng Chen
Research on Chemical Intermediates, 2019, 45 : 2327 - 2339
[44] Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3] oxathiol-4(5H)-ones via Rh2(OAc)4-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
He, Xinwei
Zhou, Yao
Shang, Yongjia
Yang, Cheng
Zuo, Youpeng
ACS OMEGA, 2016, 1 (06): : 1277 - 1283
[45] Efficient and selective azidation of per-O-acetylated sugars using ultrasound activation: application to the one-pot synthesis of 1,2,3-triazole glycosides
Marzag, Hamid
Alaoui, Soukaina
Amdouni, Hella
Martin, Anthony R.
Bougrin, Khalid
Benhida, Rachid
NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) : 5437 - 5444
[46] Novel 5-Ethoxy-5H-5λ5-[1,2,4]triazolo[5,1-e][1,4,2]diazaphosphol-5-ones: One-Pot Synthesis, Characterization, and Antimicrobial Activities
Ali, T. E.
Assiri, M. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (01) : 94 - 98
[47] Novel 5-Ethoxy-5H-5λ5-[1,2,4]triazolo[5,1-e][1,4,2]diazaphosphol-5-ones: One-Pot Synthesis, Characterization, and Antimicrobial Activities
T. E. Ali
M. A. Assiri
Russian Journal of Organic Chemistry, 2022, 58 : 94 - 98
[48] Synthesis and microbial screening of 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives
Choudhare, Tukaram S.
Wagare, Devendra S.
Kadam, Vijay T.
Netankar, Prashant D.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (08) : 1637 - 1644
[49] Bi(TFA)3 immobilized in [nbpy]FeCl4:: An efficient catalyst system for the one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones
Khosropour, Ahmad R.
Mohammadpoor-Baltork, Iraj
Ghorbankhani, Hamid
CATALYSIS COMMUNICATIONS, 2006, 7 (09) : 713 - 716
[50] Lanthanide triflate catalyzed one-pot synthesis of dihydropyrimidin-2(1H)-thiones by a three-component of 1,3-dicarbonyl compounds, aldehydes, and thiourea using a solvent-free Biginelli condensation
Wang, LM
Qian, CT
Tian, H
Ma, Y
SYNTHETIC COMMUNICATIONS, 2003, 33 (09) : 1459 - 1468

← 1 2 3 4 5 →