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

doi:10.6023/cjoc201902030

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2843-2850.DOI: 10.6023/cjoc201902030 Previous Articles Next Articles

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水相中酸性离子液体功能化β-环糊精催化合成四氢苯并[a]氧杂蒽-11-酮衍生物

刘孝庆^a, 王菲^a, 孙慧^a, 郑梦雅^a, 王华兰^b, 巩凯^a^*()

^a 江南大学药学院无锡 214122
^b 杭州师范大学有机硅化学及材料技术教育部重点实验室杭州 311121

收稿日期:2019-02-26 修回日期:2019-04-16 发布日期:2019-06-06
通讯作者: 巩凯 E-mail:gongkai@jiangnan.edu.cn
基金资助:
国家自然科学基金(51303069);国家自然科学基金(21303036);中央高校基本科研业务费专项资金(JUSRP21940);浙江省重中之重资助项目(ZX15001018)

Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed byAcid 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

Received:2019-02-26 Revised:2019-04-16 Published:2019-06-06
Contact: Gong Kai E-mail:gongkai@jiangnan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(51303069);Project supported by the National Natural Science Foundation of China(21303036);The Fundamental Research Funds for the Central Universities(JUSRP21940);The Key Disciplines in Zhejiang Province(ZX15001018)

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.

Key words: ionic liquid, β-cyclodextrin, multicomponent reactions, tetrahydrobenzo[a] xanthen-11-ones, aqueous media

Cite this article

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

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Fig. & Tab. 8

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Entry	Solvent	Catalyst	Cat./ mol%	T/℃	Time/ min	Yield^b/%
1	H₂O	—	—	r.t.	120	NR^c
2	H₂O	—	—	80	120	NR^c
3	H₂O	β-CD-AIL	3	r.t.	120	24
4	H₂O	β-CD-AIL	3	50	60	81
5	H₂O	β-CD-AIL	3	80	30	92
6	H₂O	β-CD-AIL	3	100	30	91
7	H₂O	β-CD-AIL	1	80	30	79
8	H₂O	β-CD-AIL	5	80	30	92
9	Solvent-free	β-CD-AIL	3	80	30	85
10	CH₃CH₂OH	β-CD-AIL	3	80	30	88
11	ClCH₂CH₂Cl	β-CD-AIL	3	80	30	72
12	THF	β-CD-AIL	3	80	30	68
13	CH₃CN	β-CD-AIL	3	80	30	56
14	DMF	β-CD-AIL	3	80	30	78
15	H₂O	β-CD	3	80	30	10
16	H₂O	AIL^d	3	80	30	76
17	H₂O	β-CD+AIL	3+3	80	30	81

Entry	Solvent	Catalyst	Cat./ mol%	T/℃	Time/ min	Yield^b/%
1	H₂O	—	—	r.t.	120	NR^c
2	H₂O	—	—	80	120	NR^c
3	H₂O	β-CD-AIL	3	r.t.	120	24
4	H₂O	β-CD-AIL	3	50	60	81
5	H₂O	β-CD-AIL	3	80	30	92
6	H₂O	β-CD-AIL	3	100	30	91
7	H₂O	β-CD-AIL	1	80	30	79
8	H₂O	β-CD-AIL	5	80	30	92
9	Solvent-free	β-CD-AIL	3	80	30	85
10	CH₃CH₂OH	β-CD-AIL	3	80	30	88
11	ClCH₂CH₂Cl	β-CD-AIL	3	80	30	72
12	THF	β-CD-AIL	3	80	30	68
13	CH₃CN	β-CD-AIL	3	80	30	56
14	DMF	β-CD-AIL	3	80	30	78
15	H₂O	β-CD	3	80	30	10
16	H₂O	AIL^d	3	80	30	76
17	H₂O	β-CD+AIL	3+3	80	30	81

Entry	Ar	R¹	Compd.	Time/min	Yield^b/%
1	C₆H₅	CH₃	4a	30	92
2	2-Cl-C₆H₄	CH₃	4b	30	90
3	4-Cl-C₆H₄	CH₃	4c	25	94
4	2,4-Cl₂-C₆H₄	CH₃	4d	30	88
5	4-F-C₆H₄	CH₃	4e	20	92
6	2-NO₂-C₆H₄	CH₃	4f	25	91
7	3-NO₂-C₆H₄	CH₃	4g	25	90
8	4-NO₂-C₆H₄	CH₃	4h	20	95
9	4-CH₃-C₆H₄	CH₃	4i	30	91
10	4-CH₃O-C₆H₄	CH₃	4j	35	88
11	2-HO-C₆H₄	CH₃	4k	30	82
12	4-HO-C₆H₄	CH₃	4l	30	85
13	4-N(CH₃)₂-C₆H₄	CH₃	4m	30	90
14	C₆H₅	H	4n	30	90
15	2-Cl-C₆H₄	H	4o	30	89
16	4-Cl-C₆H₄	H	4p	25	92
17	3-NO₂-C₆H₄	H	4q	25	91
18	4-NO₂-C₆H₄	H	4r	20	93
19	4-CH₃-C₆H₄	H	4s	30	90
20	4-CH₃O-C₆H₄	H	4t	40	86
21	4-OH-C₆H₄	H	4u	40	83

Entry	Ar	R¹	Compd.	Time/min	Yield^b/%
1	C₆H₅	CH₃	4a	30	92
2	2-Cl-C₆H₄	CH₃	4b	30	90
3	4-Cl-C₆H₄	CH₃	4c	25	94
4	2,4-Cl₂-C₆H₄	CH₃	4d	30	88
5	4-F-C₆H₄	CH₃	4e	20	92
6	2-NO₂-C₆H₄	CH₃	4f	25	91
7	3-NO₂-C₆H₄	CH₃	4g	25	90
8	4-NO₂-C₆H₄	CH₃	4h	20	95
9	4-CH₃-C₆H₄	CH₃	4i	30	91
10	4-CH₃O-C₆H₄	CH₃	4j	35	88
11	2-HO-C₆H₄	CH₃	4k	30	82
12	4-HO-C₆H₄	CH₃	4l	30	85
13	4-N(CH₃)₂-C₆H₄	CH₃	4m	30	90
14	C₆H₅	H	4n	30	90
15	2-Cl-C₆H₄	H	4o	30	89
16	4-Cl-C₆H₄	H	4p	25	92
17	3-NO₂-C₆H₄	H	4q	25	91
18	4-NO₂-C₆H₄	H	4r	20	93
19	4-CH₃-C₆H₄	H	4s	30	90
20	4-CH₃O-C₆H₄	H	4t	40	86
21	4-OH-C₆H₄	H	4u	40	83

水相中酸性离子液体功能化β-环糊精催化合成四氢苯并[a]氧杂蒽-11-酮衍生物

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

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