三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮

doi:10.6023/cjoc202010041

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1622-1630.DOI: 10.6023/cjoc202010041 上一篇下一篇

研究论文

三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮

刘思展^a, 崔明月^a, 王博文^a, 胡春梅^b, 郑莹莹^b, 李晶^a, 徐学涛^b^,^*(), 王震^a, 王少华^a^,^*()

a 兰州大学药学院兰州 730000
b 五邑大学生物科技与大健康学院广东江门 529020

收稿日期:2020-10-30 修回日期:2020-12-10 发布日期:2020-12-24
通讯作者: 徐学涛, 王少华
基金资助:
国家自然科学基金(21472077); 国家自然科学基金(21772071); 广东省教育厅(2017KTSCX185); 广东省教育厅(2017KSYS010); 广东省教育厅(2019KZDXM035)

Triethyl Amine-Promoted Cyclization Reaction between Cyclopropenone and α-Halogenated Hydroxamate for the Synthesis of Polysubstituted 6H-1,3-Oxazin-6-one

Sizhan Liu^a, Mingyue Cui^a, Bowen Wang^a, Chunmei Hu^b, Yingying Zheng^b, Jing Li^a, Xuetao Xu^b^,^*(), Zhen Wang^a, Shaohua Wang^a^,^*()

a School of Pharmacy, Lanzhou University, Lanzhou 730000
b School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020

Received:2020-10-30 Revised:2020-12-10 Published:2020-12-24
Contact: Xuetao Xu, Shaohua Wang
About author:
* Corresponding authors. E-mail: wangshh@lzu.edu.cn;
E-mail: wyuchemxxt@126.com
Supported by:
National Natural Science Foundation of China(21472077); National Natural Science Foundation of China(21772071); Department of Education of Guangdong Province(2017KTSCX185); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2019KZDXM035)

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摘要/Abstract

利用环丙烯酮同时具有亲核性、亲电性以及易发生开环反应的特点, 实现了三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯类化合物的[3+3]环加成反应, 快速构筑了6H-1,3-噁嗪-6-酮骨架, 为噁嗪酮类化合物的合成提供了新的思路. 该反应在无金属和温和条件下显示出良好的收率和官能团耐受性, 同时适合克级规模制备.

关键词: 环丙烯酮, α-卤代异羟肟酸酯, 环化反应, 噁嗪酮

A triethyl amine-promoted cyclization reaction between cyclopropenone and α-halohydroxamate has been developed to give an alternative synthetic strategy for the construction of 6H-1,3-oxazin-6-one skeleton. The reaction shows good yield and functional group tolerance under metal-free and mild conditions, and it is suitable for gram-scale preparation.

Key words: cyclopropenone, α-halogenated hydroxamate, cyclization reaction, oxazinone

引用此文

刘思展, 崔明月, 王博文, 胡春梅, 郑莹莹, 李晶, 徐学涛, 王震, 王少华. 三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮[J]. 有机化学, 2021, 41(4): 1622-1630.

Sizhan Liu, Mingyue Cui, Bowen Wang, Chunmei Hu, Yingying Zheng, Jing Li, Xuetao Xu, Zhen Wang, Shaohua Wang. Triethyl Amine-Promoted Cyclization Reaction between Cyclopropenone and α-Halogenated Hydroxamate for the Synthesis of Polysubstituted 6H-1,3-Oxazin-6-one[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1622-1630.

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图/表 6

图1. 生物活性分子

Figure 1. Biologically active molecules

图式1. 前人工作和本文工作

Scheme 1. Previous work and this work

图式2. 环丙烯酮[3+m]反应模式

Scheme 2. [3+m] reaction mode of cyclopropenone

Entry	Base	Solvent	Yield^b/%
1	DBU	DMF	33
2	DBU	Acetonitrile	57
3	DBU	Ether	31
4	DBU	DMSO	Trace
5	DBU	n-Heptane	n.d.^c
6	DBU	DCM	59
7	DBU	THF	58
8	DBU	Toluene	53
9	DBU	DCE	Trace
10	DBU	Dioxane	n.d.^c
11	DMAP	DCM	n.d.^c
12	Et₃N	DCM	59%
13	TEA	DCM	n.d.^c
14	DIPEA	DCM	35
15	K₂CO₃	DCM	49
16	DABCO	DCM	Trace
17	CS₂CO₃	DCM	32
18	NaH	DCM	45
19	Et₃N^d	DCM	44
20	Et₃N^e	DCM	Trace
21^f	Et₃N^g	DCM	70
22^f	Et₃N^h	DCM	75
23^f	Et₃Nⁱ	DCM	67

表1. 反应条件的优化a

Table 1. Optimization of reaction conditions

表2. 底物的适用范围a

Table 2. Substrate scope of the reaction

图式3. 可能的反应机理

Scheme 3. Plausible reaction mechanism

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三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮

Triethyl Amine-Promoted Cyclization Reaction between Cyclopropenone and α-Halogenated Hydroxamate for the Synthesis of Polysubstituted 6H-1,3-Oxazin-6-one

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