Base-Promoted Tandem Cyclization for the Synthesis of Polyfunctional 2-Hydroxy-2,3-dihydrofurans from Arylglyoxal Monohydrates and 3-(1 H -Indol-3-yl)-3-oxopropanenitrile

被引：1

作者：

Cai, Qun ^{[1
]}

Sheng, Hui-Yang ^{[1
]}

Li, Deng-Kui ^{[2
]}

Liu, Yi ^{[1
]}

Wu, An-Xin ^{[2
]}

机构：

[1] Wuhan Univ Sci & Technol, Coal Convers & New Carbon Mat Key Lab Hubei Prov, Sch Chem & Chem Engn, Wuhan 430081, Hubei, Peoples R China

[2] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

SYNLETT | 2018年 / 29卷 / 14期

基金：

中国国家自然科学基金;

关键词：

2-hydroxy-2; 3-dihydrofurans; tandem cyclization; arylglyoxal monohydrates; 3-(1H-indol-3-yl)-3-oxopropanenitrile; one pot; KNOEVENAGEL CONDENSATION; PTEROCARPUS-MARSUPIUM; ACID; POLYKETIDES; METABOLITES; ALDEHYDES; PRODUCTS; STRATEGY; KETONES; SALTS;

D O I：

10.1055/s-0037-1609555

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient base-promoted tandem cyclization for the synthesis of polyfunctional 2-hydroxy-2,3-dihydrofurans from arylglyoxal monohydrates and 3-(1 Hindol-3-yl)-3-oxopropanenitrile has been established. The investigation of the mechanism suggested that this reaction proceeds through a Knoevenagel condensation-Michael addition-oxidation-cyclization sequence. This method demonstrates the compatibility with a wide range of functional groups to produce the 2-hydroxy-2,3-dihydrofuran scaffolds in good to excellent yields in one pot.

引用

页码：1926 / 1932

页数：7

共 50 条

[1] CHEMISTRY OF 3-(1H-INDOL-3-YL)-3-OXOPROPANENITRILE
Fadda, Ahmed A.
El-Mekabaty, Ahmed
Mousa, Ibrahim A.
Elattar, Khaled M.
SYNTHETIC COMMUNICATIONS, 2014, 44 (11) : 1579 - 1599
[2] Synthesis of New Heterocycles Derived from 3-(3-Methyl-1H-indol-2-yl)-3-oxopropanenitrile as Potent Antifungal Agents
Gomha, Sobhi M.
Abdel-Aziz, Hatem A.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (09): : 2985 - 2990
[3] Base-Promoted Tandem Cyclization of 2-(Indol-3-yl)naphthoquinones with Benzamidines toward Polysubstituted Pyrimido[4,5-b]indoles
Tan, Bin
Hu, Kai
Zhang, Chao
Zhou, Xinlin
Deng, Guo-Jun
Chen, Shanping
ORGANIC LETTERS, 2024, 26 (38) : 8034 - 8039
[4] Oxidative photochemical cyclization of ethyl 3-(indol-3-yl)-3-oxo-2-phenylpropanoate derivatives: synthesis of benzo[a]carbazoles
Li, Yinlong
Pang, Zhonghua
Zhang, Tianqi
Yang, Jidong
Yu, Wei
TETRAHEDRON, 2015, 71 (21) : 3351 - 3358
[5] Design and Efficient Synthesis of Some Azole and Thiazole Systems Based 3-(1,3-Dioxoisoindolin-2-yl)-3-oxopropanenitrile
El Aazab, Islam Helmy
El Latif, Fawi Mohamed Abd
LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (03) : 187 - 196
[6] An ultrasound-promoted green approach for the synthesis of 3-(indol-3-yl)-3-hydroxyindolin-2-ones catalyzed by Fe(III)
Khorshidi, Alireza
Tabatabaeian, Khalil
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2011, 76 (10) : 1347 - 1353
[7] Quantum chemical study of the transformation of 2-(N-alkylamino)-3-(indol-1-yl)-and 2-(N-alkylamino)-3-(indol-3-yl)maleimides by protic acids:: Tandem hydride transfer/cyclization mechanism
Bykov, E. E.
Lakatosh, S. A.
Preobrazhenskaya, M. N.
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (12) : 2149 - 2153
[8] Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3-(1,4-Dioxo-3,4-dihydrophthalazin-2(1H)-yl)-3-oxopropanenitrile as Precursors
Khidre, Rizk E.
Radini, Ibrahim Ali M.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (03) : 850 - 858
[9] Quantum chemical study of the transformation of 2-(N-alkylamino)-3-(indol-1-yl)-and 2-(N-alkylamino)-3-(indol-3-yl)maleimides by protic acids: Tandem hydride transfer/cyclization mechanism
E. E. Bykov
S. A. Lakatosh
M. N. Preobrazhenskaya
Russian Chemical Bulletin, 2006, 55 : 2149 - 2153
[10] 2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene]-3-oxopropanenitrile
Helliwell, Madeleine
Baradarani, Mehdi M.
Mohammadnejadaghdam, Razieh
Afghan, Arash
Joule, John A.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : o233

← 1 2 3 4 5 →