Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride

doi:10.6023/cjoc202007070

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 731-737.DOI: 10.6023/cjoc202007070 Previous Articles Next Articles

Article

乙酸酐促进的[3+3]环化反应合成2-喹啉酮衍生物

赵瑜¹, 陈卓¹, 陈雪冰¹^,^*()

1 红河学院理学院云南蒙自 661199

收稿日期:2020-07-30 修回日期:2020-08-25 发布日期:2020-09-22
通讯作者: 陈雪冰
作者简介:
* Corresponding author. E-mail: orangekaka@126.com
基金资助:
云南省科技厅项目(2017FD156); 云南省高校科技创新团队资助项目.

Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride

Yu Zhao¹, Zhuo Chen¹, Xuebing Chen¹^,^*()

1 School of Science, Honghe University, Mengzi, Yunnan 661199

Received:2020-07-30 Revised:2020-08-25 Published:2020-09-22
Contact: Xuebing Chen
Supported by:
the Applied Basic Research Project of Yunnan(2017FD156); the Program for Innovative Research Team Technology) in University of Yunnan Province

1. cjoc202007070.pdf(2397KB)

Abstract

2-Quinolinone unit is frequently found in both natural products and pharmaceuticals. Furthermore, they are important heterocycle building blocks. Herein, a novel approach to the synthesis of 2-quinolinone derivatives has been established from [3+3] cyclization of β-enaminones with malonic acid promoted by acetic anhydride with yields of 70%~87%. The reaction is particularly attractive due to following advantages: simple starting materials, operational simplicity, concise synthetic route, easy purification, highly modifiability of target molecules and so on.

Key words: Keywords β-enaminones, 2-quinolinones, [3+3] cyclization, acetic anhydride promoted

Cite this article

Yu Zhao, Zhuo Chen, Xuebing Chen. Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 731-737.

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References 17

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Entry	Solvent	Additive	T/℃	t/h	Yield^b/%
1	EtOH	—	r.t.	4	N.R.
2	EtOH	—	Reflux	4	N.R.
3	EtOH	HOAc	Reflux	4	N.R
4	EtOH	CF₃COOH	Reflux	4	N.R
5	EtOH	CF₃SO₃H	Reflux	4	N.R
6	EtOH	DBU	Reflux	4	N.R
7	EtOH	Piperidine	Reflux	4	N.R.
8	EtOH	Ac₂O	Reflux	2	60
9	EtOH	Ac₂O	50	2	70
10	CH₃CN	Ac₂O	50	2	67
11	HOAc	Ac₂O	50	2	75
12	Ac₂O	Ac₂O	50	2	84
13	Ac₂O	Ac₂O	r.t	2	N.R.
14	Ac₂O	TsOH	50	2	15
15	CH₂Cl₂	DCC/DMAP	r.t	4	N.R.
16^c	Ac₂O	Ac₂O	50	4	86
17^d	Ac₂O	Ac₂O	50	4	N.R.

Entry	Solvent	Additive	T/℃	t/h	Yield^b/%
1	EtOH	—	r.t.	4	N.R.
2	EtOH	—	Reflux	4	N.R.
3	EtOH	HOAc	Reflux	4	N.R
4	EtOH	CF₃COOH	Reflux	4	N.R
5	EtOH	CF₃SO₃H	Reflux	4	N.R
6	EtOH	DBU	Reflux	4	N.R
7	EtOH	Piperidine	Reflux	4	N.R.
8	EtOH	Ac₂O	Reflux	2	60
9	EtOH	Ac₂O	50	2	70
10	CH₃CN	Ac₂O	50	2	67
11	HOAc	Ac₂O	50	2	75
12	Ac₂O	Ac₂O	50	2	84
13	Ac₂O	Ac₂O	r.t	2	N.R.
14	Ac₂O	TsOH	50	2	15
15	CH₂Cl₂	DCC/DMAP	r.t	4	N.R.
16^c	Ac₂O	Ac₂O	50	4	86
17^d	Ac₂O	Ac₂O	50	4	N.R.

Entry	R	R¹	1	3	Yield^b/%
1	4-FC₆H₄	H	1a	3a	82
2	3-FC₆H₄	H	1b	3b	87
3	4-ClC₆H₄	H	1c	3c	80
4	3-ClC₆H₄	H	1d	3d	81
5	2-ClC₆H₄	H	1e	3e	76
6	4-BrC₆H₄	H	1f	3f	78
7	3-BrC₆H₄	H	1g	3g	81
8	4-CH₃C₆H₄	H	1h	3h	80
9	3-CH₃C₆H₄	H	1i	3i	75
10	4-NO₂C₆H₄	CH₃	1j	3j	70
11	4-FC₆H₄	CH₃	1k	3k	81
12	3-FC₆H₄	CH₃	1l	3l	84
13	4-ClC₆H₄	CH₃	1m	3m	85
14	3-ClC₆H₄	CH₃	1n	3n	82
15	4-BrC₆H₄	CH₃	1o	3o	85
16	C₆H₅	CH₃	1p	3p	83
17	4-CH₃C₆H₄	CH₃	1q	3q	79
18	3-CH₃C₆H₄	CH₃	1r	3r	80
19	3-CH₃C₆H₄	CH₃	1s	3s	83
20	Butyl	CH₃	1t	3t’	25

Entry	R	R¹	1	3	Yield^b/%
1	4-FC₆H₄	H	1a	3a	82
2	3-FC₆H₄	H	1b	3b	87
3	4-ClC₆H₄	H	1c	3c	80
4	3-ClC₆H₄	H	1d	3d	81
5	2-ClC₆H₄	H	1e	3e	76
6	4-BrC₆H₄	H	1f	3f	78
7	3-BrC₆H₄	H	1g	3g	81
8	4-CH₃C₆H₄	H	1h	3h	80
9	3-CH₃C₆H₄	H	1i	3i	75
10	4-NO₂C₆H₄	CH₃	1j	3j	70
11	4-FC₆H₄	CH₃	1k	3k	81
12	3-FC₆H₄	CH₃	1l	3l	84
13	4-ClC₆H₄	CH₃	1m	3m	85
14	3-ClC₆H₄	CH₃	1n	3n	82
15	4-BrC₆H₄	CH₃	1o	3o	85
16	C₆H₅	CH₃	1p	3p	83
17	4-CH₃C₆H₄	CH₃	1q	3q	79
18	3-CH₃C₆H₄	CH₃	1r	3r	80
19	3-CH₃C₆H₄	CH₃	1s	3s	83
20	Butyl	CH₃	1t	3t’	25

乙酸酐促进的[3+3]环化反应合成2-喹啉酮衍生物

Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride

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