Base- and Copper-Catalyzed Intramolecular Cyclization for the Direct Synthesis of Dihydrofurans

被引：30

作者：

Chen, Yong-Fei ^{[1
]}

Wang, Hai-Fei ^{[1
]}

Wang, Ya ^{[1
]}

Luo, Yong-Chun ^{[1
]}

Zhu, Hai-Liang ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 07期

关键词：

alkynes; copper; cyclization; dihydrofurans; furans; HIGHLY EFFICIENT SYNTHESIS; SUBSTITUTED FURANS; COUPLING REACTIONS; C-N; 1,3-DICARBONYL COMPOUNDS; PROPARGYLIC ALCOHOLS; FACILE SYNTHESIS; PALLADIUM; CYCLOISOMERIZATION; ANNULATION;

D O I：

10.1002/adsc.201000005

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A simple and convenient synthetic approach to dihydrofurans has been developed from the cyclization of 2-propynyl-1,3-dicarbonyl compounds catalyzed by potassium tert-butoxide, copper(II) trifluoromethanesulfonate and triphenylphosphine using methanol/dichloromethane as the solvent under very mild conditions. Moreover, dihydrofurans could be easily transformed into the corresponding furans in the presence of trifluoroacetic acid.

引用

页码：1163 / 1168

页数：6

共 50 条

[31] A gold-catalyzed facile intramolecular rearrangement and cyclization sequence for synthesis of 2,5-dihydrofurans
Sunil, Komalla
Thummala, Yadagiri
Dalovai, Purnachandar
Balasubramanian, Sridhar
Karunakar, Galla V.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (24) : 6015 - 6024
[32] Copper-catalyzed cyclization of iodo-tryptophans:: A straightforward synthesis of pyrroloindoles
Coste, Alexis
Toumi, Mathieu
Wright, Karen
Razafimahaleo, Vanessa
Couty, Francois
Marrot, Jerome
Evano, Gwilherm
ORGANIC LETTERS, 2008, 10 (17) : 3841 - 3844
[33] SYNTHESIS OF TRICYCLIC KETONES BY COPPER-CATALYZED CYCLIZATION OF MONOCYCLIC OLEFINIC DIAZOKETONES
DOERING, WVE
FOSSEL, ET
KAYE, RL
TETRAHEDRON, 1965, 21 (01) : 25 - &
[34] Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes
Zhang, HM
Larock, RC
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7048 - 7056
[35] Copper-Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines
Xu, Miao
Jiang, Jia-Tian
Dong, Hao-Xuan
Wang, Guang-Hui
Zhou, Bo
Ye, Long-Wu
ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (02)
[36] Copper-catalyzed cyclization reaction for the synthesis of bicyclic α-carbonyl furan derivatives
Hamal, Khagendra
Chalifoux, Wesley
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[37] Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines
Chatterjee, Rana
Pothireddy, Mohanreddy
Dandela, Rambabu
SYNLETT, 2023, 34 (09) : 1058 - 1062
[38] Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization
Deng, Xu
Liang, Kangjiang
Tong, Xiaogang
Ding, Ming
Li, Dashan
Xia, Chengfeng
TETRAHEDRON, 2015, 71 (22) : 3699 - 3704
[39] Sequential copper-catalyzed vinylation/cyclization: An efficient synthesis of functionalized oxazoles
Martin, Rubn
Cuenca, Ana
Buchwald, Stephen L.
ORGANIC LETTERS, 2007, 9 (26) : 5521 - 5524
[40] Copper-catalyzed cyclization reaction: Unique synthesis of condensed thiazoles and selenazoles
Heravi, MM
Oskooie, HA
Fahimi, M
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (06): : 587 - 589

← 1 2 3 4 5 →