Citation: Liu Xiaoqin, Wang Fei, Sun Hui, Zheng Mengya, Wang Hualan, Gong Kai. Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed by Acid Ionic Liquid Functionalized β-Cyclodextrin in Water[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2843-2850. doi: 10.6023/cjoc201902030 shu

Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed by Acid Ionic Liquid Functionalized β-Cyclodextrin in Water

Liu Xiaoqin ^a ,
Wang Fei ^a ,
Sun Hui ^a ,
Zheng Mengya ^a ,
Wang Hualan ^b ,
Gong Kai ^a,,

a.
School of Pharmaceutical Science, Jiangnan University, Wuxi 214122
b.
Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121

Corresponding author: Gong Kai, gongkai@jiangnan.edu.cn
Received Date: 26 February 2019
Revised Date: 16 April 2019
Available Online: 6 October 2019
Fund Project: the National Natural Science Foundation of China JUSRP21940Project supported by the National Natural Science Foundation of China (Nos. 51303069, 21303036), the Fundamental Research Funds for the Central Universities (No. JUSRP21940), and the Key Disciplines in Zhejiang Province (No. ZX15001018)the Key Disciplines in Zhejiang Province ZX15001018the Fundamental Research Funds for the Central Universities ZX15001018the National Natural Science Foundation of China 5130306

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Taking advantage of biocompatible β-cyclodextrin (β-CD) and ionic liquid (IL), β-cyclodextrin functionalized with acid ionic liquid (β-CD-AIL) was prepared and characterized by FT-IR, ¹H NMR and ¹³C NMR. β-CD-AIL was evaluated as catalyst for the preparation of 12-aryl-8, 9, 10, 12-tetrahydrobenzo[a]xanthen-11-ones via one-pot condensation reaction of β-naphthol, aromatic aldehydes and cyclic 1, 3-dicarbonyl compounds. The results showed that β-CD-AIL behaved excellent efficiency and recyclability. The key benefits of this protocol involve mild reaction conditions, fast reaction speed, good to excellent yields and simple operational procedure.
- ionic liquid,
- β-cyclodextrin,
- multicomponent reactions,
- tetrahydrobenzo[a] xanthen-11-ones,
- aqueous media
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