A Four-Component Reaction for the Synthesis of Dispirotetrahydro-quinoline-bis(1,3-dioxane-4,6-dione) Derivatives Catalyzed by Tartaric Acid

doi:10.6023/cjoc202008051

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2127-2133.DOI: 10.6023/cjoc202008051 Previous Articles Next Articles

NOTES

酒石酸催化四组分反应合成双螺环四氢喹啉双(1,3-二噁烷-4,6-二酮)衍生物

许招会^a^,^*(), 叶华涛^a, 张文峰^a, 肖强^b^,^*()

a 江西师范大学化学化工学院南昌 330022
b 江西省人民医院骨科南昌 330006

收稿日期:2020-08-27 修回日期:2020-12-13 发布日期:2020-12-31
通讯作者: 许招会, 肖强
基金资助:
江西省研究生创新基金(YC2015-B023); 江西省教育厅科技计划研究项目(GJJ170170); 江西省教育厅科技计划研究项目(GJJ180892); 江西师范大学博士科研启动基金(JXSDBY2020-B012)

A Four-Component Reaction for the Synthesis of Dispirotetrahydro-quinoline-bis(1,3-dioxane-4,6-dione) Derivatives Catalyzed by Tartaric Acid

Zhaohui Xu^a^,^*(), Huatao Ye^a, Wenfeng Zhang^a, Qiang Xiao^b^,^*()

a Chemistry and Chemical Engineering Department, Jiangxi Normal University, Nanchang 330022
b Department of Orthopedics, Jiangxi Province People?s Hospital, Nanchang 330006

Received:2020-08-27 Revised:2020-12-13 Published:2020-12-31
Contact: Zhaohui Xu, Qiang Xiao
About author:
* Corresponding authors. E-mail: gotoxzh@163.com;
E-mail: jxxiaoq@163.com
Supported by:
Graduate Innovation Foundation of Jiangxi Province(YC2015-B023); Science and Technology Research Project of Jiangxi Provincial Education Department(GJJ170170); Science and Technology Research Project of Jiangxi Provincial Education Department(GJJ180892); Jiangxi Normal University Doctoral Research Initiation Fund Project(JXSDBY2020-B012)

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Abstract

Eleven dispirotetrahydroquinoline-bis(1,3-dioxane-4,6-dione) derivatives were synthesized by a four-component reaction of 1,3-dioxane-4,6-dione, aromatic aldehydes, arylamines and acetone in the presence of tartaric acid. This method can provide the advantages of high yields, broader substrate scope, mild conditions, simple operation and environmental friendliness. Additionally, the reaction mechanism was also speculated.

Key words: tartaric acid, four-component reaction, 1,3-dioxane-4,6-dione, dispirotetrahydroquinoline-bis(1,3-dioxane-4,6- dione) derivative

Cite this article

Zhaohui Xu, Huatao Ye, Wenfeng Zhang, Qiang Xiao. A Four-Component Reaction for the Synthesis of Dispirotetrahydro-quinoline-bis(1,3-dioxane-4,6-dione) Derivatives Catalyzed by Tartaric Acid[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2127-2133.

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Fig. & Tab. 6

References 31

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Entry	Solvent	Catalyst (mol%)	Time/h	Yield^b/%
1	H₂O	None	32	12
2	CH₃CH₂OH	None	32	21
3	CH₃COCH₃	None	32	24
4	CH₃CN	None	32	35
5	CH₃CN	ZnSO₄?7H₂O (15)	24	0
6	CH₃CN	B(OH)₃ (15)	24	0
7	CH₃CN	Iodine (15)	24	52
8	CH₃CN	Malonic acid (15)	24	46
9	CH₃CN	Benzoic acid (15)	24	60
10	CH₃CN	CCl₃CO₂H (15)	24	69
11	CH₃CN	L-Proline	24	54
12	CH₃CN	Tartaric acid (15)	20	85
13	CH₃CN	Tartaric acid (10)	24	63
14	CH₃CN	Tartaric acid (20)	24	85
15	CH₃CN	Tartaric acid (15)	16	72
16	CH₃CN	Tartaric acid (15)	24	84

Entry	Solvent	Catalyst (mol%)	Time/h	Yield^b/%
1	H₂O	None	32	12
2	CH₃CH₂OH	None	32	21
3	CH₃COCH₃	None	32	24
4	CH₃CN	None	32	35
5	CH₃CN	ZnSO₄?7H₂O (15)	24	0
6	CH₃CN	B(OH)₃ (15)	24	0
7	CH₃CN	Iodine (15)	24	52
8	CH₃CN	Malonic acid (15)	24	46
9	CH₃CN	Benzoic acid (15)	24	60
10	CH₃CN	CCl₃CO₂H (15)	24	69
11	CH₃CN	L-Proline	24	54
12	CH₃CN	Tartaric acid (15)	20	85
13	CH₃CN	Tartaric acid (10)	24	63
14	CH₃CN	Tartaric acid (20)	24	85
15	CH₃CN	Tartaric acid (15)	16	72
16	CH₃CN	Tartaric acid (15)	24	84

Entry	Compound 1	Ar¹ (2)	Ar² (3)	Time/h	Product	Yield^b/%
1	1a	C₆H₅ (2a)	C₆H₅ (3a)	20	5a	85
2	1a	4-FC₆H₄ (2b)	C₆H₅ (3a)	16	5b	74
3	1a	4-ClC₆H₄ (2c)	C₆H₅ (3a)	18	5c	81
4	1a	4-MeC₆H₄ (2d)	C₆H₅ (3a)	24	5d	78
5	1a	4-CH₃OC₆H₄ (2f)	C₆H₅ (3a)	30	5e	75
6^c	1a	4-(CH₃)₂NC₆H₄ (2g)	C₆H₅ (3a)	24	—	—
7^c	1a	2-Furyl (2h)	C₆H₅ (3a)	24	—	—
8	1a	C₆H₅ (2a)	4-FC₆H₄ (3b)	24	5f	68
9	1a	C₆H₅ (2a)	4-BrC₆H₄ (3c)	24	5g	71
10	1a	C₆H₅ (2a)	4-ClC₆H₄ (3d)	24	5h	73
11	1a	C₆H₅ (2a)	4-CH₃OC₆H₄ (3e)	30	5i	69
12	1b	C₆H₅ (2a)	C₆H₅ (3a)	20	5j	83
13	1c	C₆H₅ (2a)	C₆H₅ (3a)	20	5k	86

Entry	Compound 1	Ar¹ (2)	Ar² (3)	Time/h	Product	Yield^b/%
1	1a	C₆H₅ (2a)	C₆H₅ (3a)	20	5a	85
2	1a	4-FC₆H₄ (2b)	C₆H₅ (3a)	16	5b	74
3	1a	4-ClC₆H₄ (2c)	C₆H₅ (3a)	18	5c	81
4	1a	4-MeC₆H₄ (2d)	C₆H₅ (3a)	24	5d	78
5	1a	4-CH₃OC₆H₄ (2f)	C₆H₅ (3a)	30	5e	75
6^c	1a	4-(CH₃)₂NC₆H₄ (2g)	C₆H₅ (3a)	24	—	—
7^c	1a	2-Furyl (2h)	C₆H₅ (3a)	24	—	—
8	1a	C₆H₅ (2a)	4-FC₆H₄ (3b)	24	5f	68
9	1a	C₆H₅ (2a)	4-BrC₆H₄ (3c)	24	5g	71
10	1a	C₆H₅ (2a)	4-ClC₆H₄ (3d)	24	5h	73
11	1a	C₆H₅ (2a)	4-CH₃OC₆H₄ (3e)	30	5i	69
12	1b	C₆H₅ (2a)	C₆H₅ (3a)	20	5j	83
13	1c	C₆H₅ (2a)	C₆H₅ (3a)	20	5k	86

酒石酸催化四组分反应合成双螺环四氢喹啉双(1,3-二噁烷-4,6-二酮)衍生物

A Four-Component Reaction for the Synthesis of Dispirotetrahydro-quinoline-bis(1,3-dioxane-4,6-dione) Derivatives Catalyzed by Tartaric Acid

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