Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

被引：15

作者：

Inagaki, Sho ^{[1
]}

Saito, Kai ^{[1
]}

Suto, Soichiro ^{[1
]}

Aihara, Hiromi ^{[1
]}

Sugawara, Aoi ^{[1
]}

Tamura, Satoru ^{[1
]}

Kawano, Tomikazu ^{[1
]}

机构：

[1] Iwate Med Univ, Sch Pharm, Dept Med & Organ Chem, Yahaba, Iwate 0283694, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 22期

关键词：

BETA-DIKETONES; FACILE SYNTHESIS; 3(2H)-FURANONES; CONSTRUCTION; INHIBITORS; ARYLATION; KETONES; ESTERS; ROUTE;

D O I：

10.1021/acs.joc.8b02153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-induced intramolecular cyclization of novel (4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts prepared from the commercially available 1-arylethanone by a cost-effective process is described in this paper. The reaction was completed within 10 min to produce a family of 2-unsubstituted S-aryl-3(2H)-furanones in excellent yield. This procedure is simple, and can be carried out under mild conditions and an ambient atmosphere.

引用

页码：13834 / 13846

页数：13

共 50 条

[21] Decarboxylative Knoevenagel-Type Reactions on Tetronamides: Synthesis of 5-Ylidene-4-Amino-2(5H)-Furanones
Ear, Alexandre
Toum, Valerie
Thorimbert, Serge
Dechoux, Luc
SYNLETT, 2014, 25 (12) : 1713 - 1716
[22] Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: Application to the biomimetic synthesis of merrekentrone C
Gryparis, Charis
Lykakis, Ioannis N.
Efe, Christina
Zaravinos, Ioannis-Panayotis
Vidali, Theonymphi
Kladou, Eugenia
Stratakis, Manolis
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5655 - 5658
[23] Gold-catalyzed Reactions of 3-Alkynyloxireno[2, 3-b]chromenones to Form 3(2H)-Furanones via a Domino Pathway
Hu, Feng
Yan, Jianwei
Cheng, Ming
Hu, Youhong
CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (02) : 482 - 487
[24] Computer-Assisted Design of Ionic Liquids for Efficient Synthesis of 3(2H)-Furanones: A Domino Reaction Triggered by CO2
Chen, Kaihong
Shi, Guiling
Zhang, Weidong
Li, Haoran
Wang, Congmin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (43) : 14198 - 14201
[25] Enantioselective Michael addition of 3(2H)-furanones to α,β-unsaturated aldehydes catalyzed by a diphenylprolinol silyl ether
He, Wujun
Jing, Linhai
Qin, Dabin
Xie, Xiaohua
Wu, Song
Wang, Rongming
TETRAHEDRON LETTERS, 2014, 55 (01) : 209 - 211
[26] Visible light driven metal- free intramolecular cyclization: a facile synthesis of 3-position substituted 3,4-dihydroisoquinolin-1( 2H)- one+
Zou, Shuai
Geng, Shu
Chen, Lina
Wang, Haitao
Huang, Feng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (02) : 380 - 387
[27] Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings
Xue, Fu-Ling
Li, Jian-Xiao
Wang, Zhao-Yang
Xiong, Jin-Feng
Li, Di
RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) : 1153 - 1168
[28] Copper-Catalyzed Olefinic C(sp2)-H Activation/Carbene Insertion/Ester Hydrolysis/Cyclization with Aryl Diazo Esters for the Synthesis of Multisubstituted Furanones
Wang, Yuzhi
Yu, Yadong
Yu, Yang
Huang, Fei
Baell, Jonathan B.
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (15) : 2601 - 2606
[29] A Domino Reaction of α,β-Acetylenic γ-Hydroxy Nitriles with Arenecarboxylic Acids: An Unexpected Facile Shortcut to 4-Cyano-3(2H)-furanones
Trofimov, Boris A.
Shemyakina, Olesya A.
Mal'kina, Anastasiya G.
Ushakov, Igor' A.
Kazheva, Olga N.
Alexandrov, Grigorii G.
Dyachenko, Oleg A.
ORGANIC LETTERS, 2010, 12 (14) : 3200 - 3203
[30] Effective synthesis of 5-aryl-3-ethylidene-3H-pyrrol-2-ones
Yegorova, A. Yu.
Kamneva, I. E.
Shtykova, L. S.
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (04) : 718 - 721

← 1 2 3 4 5 →