Stereoselective Synthesis of Multifunctional Spirooxindole-Dihydrofuran Derivatives

被引：4

作者：

Azimi, Razieh ^{[1
]}

Baharfar, Robabeh ^{[2
]}

Bagheri, Hashem ^{[2
]}

机构：

[1] Agr Res Educ & Extens Org AREEO, Res Inst Forests & Rangelands, Tehran, Iran

[2] Univ Mazandaran, Fac Chem, Babolsar, Iran

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2022年 / 42卷 / 08期

关键词：

Isatin; multicomponent reaction; multifunctional spirooxindole-dihydrofurans; stereoselective synthesis; POT MULTICOMPONENT SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; EFFICIENT; ANTIOXIDANT; DESIGN; YLIDES; SBA-15; DABCO;

D O I：

10.1080/10406638.2021.1933106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient protocol for the diastereoselective synthesis of novel spirooxindole-dihydrofurans has been developed by the three-component condensation of isatin derivatives, 3-cyanoacetyl indole, and N-phenacylpyridinium bromide in the presence of triethylamine base. The reaction was carried out in ethanol under reflux conditions, and various dihydrofuranyl spirooxindoles were obtained in high yields with good to excellent stereoselectivity.

引用

页码：5272 / 5281

页数：10

共 31 条

[1]

Arulananda Babu S., 2015, Stud. Nat. Prod. Chem., V46, P227, DOI [10.1016/B978-0-444-63462-7.00008-7, 10.1016/b978-0-444-63462-7.00008-7]

[2] DABCO-functionalized mesoporous SBA-15: an efficient and recyclable catalyst for the synthesis of spiro-pyranoxindoles as antioxidant agents [J].

Azimi, Razieh ;

Baharfar, Robabeh .

CANADIAN JOURNAL OF CHEMISTRY, 2014, 92 (12) :1163-1168

[3] Efficient microwave-assisted diastereoselective synthesis of indole-based 4,5-dihydrofurans via a one-pot, three-component reaction in water [J].

Baharfar, Robabeh ;

Azimi, Razieh ;

Asdollahpour, Zeinab .

ENVIRONMENTAL CHEMISTRY LETTERS, 2018, 16 (02) :677-682

[4] Three-component synthesis of novel spirooxindole-furan derivatives using pyridinium salts [J].

Baharfar, Robabeh ;

Asghari, Sakineh ;

Zaheri, Farya ;

Shariati, Narges .

COMPTES RENDUS CHIMIE, 2017, 20 (04) :359-364

[5] Sulfanilic acid functionalized mesoporous SBA-15: A water-tolerant solid acid catalyst for the synthesis of uracil fused spirooxindoles as antioxidant agents [J].

Baharfar, Robabeh ;

Azimi, Razieh .

JOURNAL OF CHEMICAL SCIENCES, 2015, 127 (08) :1389-1395

[6] IMMOBILIZATION OF 1,4-DIAZABICYCLO[2.2.2] OCTANE (DABCO) OVER MESOPOROUS SILICA SBA-15: AN EFFICIENT APPROACH FOR THE SYNTHESIS OF FUNCTIONALIZED SPIROCHROMENES [J].

Baharfar, Robabeh ;

Azimi, Razieh .

SYNTHETIC COMMUNICATIONS, 2014, 44 (01) :89-100

[7] New class of potent antitumor acylhydrazone derivatives containing furan [J].

Cui, Zining ;

Li, Ying ;

Ling, Yun ;

Huang, Juan ;

Cui, Jingrong ;

Wang, Ruiqing ;

Yang, Xinling .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) :5576-5584

[8] Antitumor Agents. 266. Design, Synthesis, and Biological Evaluation of Novel 2-(Furan-2-yl)naphthalen-1-ol Derivatives as Potent and Selective Antibreast Cancer Agents [J].

Dong, Yizhou ;

Shi, Qian ;

Liu, Yi-Nan ;

Wang, Xiang ;

Bastow, Kenneth F. ;

Lee, Kuo-Hsiung .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (11) :3586-3590

[9] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[10] A Review of Cyanoacetyl Indoles (CAIs): Versatile Starting Materials in Organic Synthesis [J].

Govender, Thavendran ;

Maguire, Glenn E. M. ;

Kruger, Hendrik G. ;

Shiri, Morteza .

CURRENT ORGANIC SYNTHESIS, 2013, 10 (05) :737-750

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