无金属参与下不饱和酰胺与多氯甲烷的串联环化反应

doi:10.6023/cjoc202102035

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3106-3115.DOI: 10.6023/cjoc202102035 上一篇下一篇

研究论文

无金属参与下不饱和酰胺与多氯甲烷的串联环化反应

葛雅欣^a, 闫芹芹^a, 田云飞^b^,^*(), 王海军^a, 张春芳^a^,^*(), 李泽江^a^,^*()

a 河北大学化学与环境科学学院药物化学与分子诊断教育部重点实验室河北省化学生物学重点实验室河北保定 071002
b 洛阳师范学院化学化工学院河南省功能导向多孔材料重点实验室河南洛阳 471934

收稿日期:2021-02-20 修回日期:2021-04-17 发布日期:2021-06-02
通讯作者: 田云飞, 张春芳, 李泽江
基金资助:
国家自然科学基金(21702044); 国家自然科学基金(11704024); 国家自然科学基金(21973024); 河北省自然科学基金(B2020201014); 河北省自然科学基金(B2020201006); 河北省高等学校科学技术研究(QN2019063); 河南省高等学校重点科研(21A150038); 河南省自然科学基金(162300410200)

Metal-Free-Involved Cascade Cyclization of Unsaturated Amides with Polychloromethanes

Yaxin Ge^a, Qinqin Yan^a, Yunfei Tian^b(), Haijun Wang^a, Chunfang Zhang^a(), Zejiang Li^a()

a Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science, Hebei University, Baoding, Hebei 071002
b Henan Key Laboratory of Function-Oriented Porous Materia, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471934

Received:2021-02-20 Revised:2021-04-17 Published:2021-06-02
Contact: Yunfei Tian, Chunfang Zhang, Zejiang Li
Supported by:
National Natural Science Foundation of China(21702044); National Natural Science Foundation of China(11704024); National Natural Science Foundation of China(21973024); Natural Science Foundation of Hebei Province(B2020201014); Natural Science Foundation of Hebei Province(B2020201006); Science and Technology Project of Hebei Education Department(QN2019063); Key Scientific Research Project of Higher Education of Henan Province(21A150038); Natural Science Foundation of Henan Province(162300410200)

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摘要/Abstract

发展了一类自由基引发不饱和酰胺与多氯甲烷的串联合环反应, 该体系提供了一种可选择性地生成多氯甲基取代的异喹啉酮或二氢异喹啉酮的方法. 同时, 在该工作中开展了机理研究和光学实验.

关键词: 不饱和酰胺, 多氯甲烷, 自由基反应, 异喹啉酮, 二氢异喹啉酮

Free radical initiated cascade cyclization of unsaturated amides with polychloromethanes provides a protocol for the selective synthesis of polychlorinated isoquinolinones, or dihydroisoquinolinones. A series of mechanistic studies and optical experiments were operated in this system.

Key words: unsaturated amide, polychloromethane, radical reaction, isoquinolinone, dihydroisoquinolinone

引用此文

葛雅欣, 闫芹芹, 田云飞, 王海军, 张春芳, 李泽江. 无金属参与下不饱和酰胺与多氯甲烷的串联环化反应[J]. 有机化学, 2021, 41(8): 3106-3115.

Yaxin Ge, Qinqin Yan, Yunfei Tian, Haijun Wang, Chunfang Zhang, Zejiang Li. Metal-Free-Involved Cascade Cyclization of Unsaturated Amides with Polychloromethanes[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3106-3115.

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图/表 6

Entry	Catalyst (mol%)	Initiator (equiv.)	Solvent (mL)	Yield^b/%
1	KI (5)	DTBP (5.0)	Chloroform (7)	37
2	KI (5)	DCP (5.0)	Chloroform (7)	60
3	KI (5)	TBCP (5.0)	Chloroform (7)	49
4	KI (5)	TBPB (5.0)	Chloroform (7)	39
5	KI (5)	DCP (3.0)	Chloroform (7)	25
6	KI (5)	DCP (4.0)	Chloroform (7)	32
7	KI (5)	DCP (6.0)	Chloroform (7)	38
8	KI (10)	DCP (5.0)	Chloroform (7)	33
9	NIS (5)	DCP (5.0)	Chloroform (7)	46
10	NaI (5)	DCP (5.0)	Chloroform (7)	50
11	KI (5)	DCP (5.0)	Chloroform (3)	44
12	KI (5)	DCP (5.0)	Chloroform (5)	38
13^c	KI (5)	DCP (5.0)	Chloroform (7)	26
14^d	KI (5)	DCP (5.0)	Chloroform (7)	Trace
15^e	KI (5)	DCP (5.0)	Chloroform (7)	Trace

表1. 反应条件优化a

Table 1. Optimization of the typical conditions

Substrate 1	Product 2	Substrate 1	Product 2

表2. N-烯丙基苯甲酰胺与氯仿的串联环化反应a

Table 2. Cascade cyclization of N-allylbenzamides with chloroform

Substrate 1	Product 3	Substrate 1	Product 3

表3. N-烯丙基苯甲酰胺与二氯甲烷的串联环化反应a

Table 3. Cascade cyclization of N-allylbenzamides with dichloromethane

图式1. N-烯丙基苯甲酰胺与多氯甲烷反应的控制实验

Scheme 1. Control experiments of the reactions of N-allylbenzamides with polychloromethanes

图式2. N-烯丙基苯甲酰胺与多氯甲烷反应的可能机理

Scheme 2. Plausible mechanism of the reactions of N-allylbenzamides with polychloromethanes

图1. 产物2h的光学研究

Figure 1. Optical study of product 2h UV/Vis absorption (c=300 μmol/L in CH3CN), PLE spectra (c=10 μmol/L) and PL (c=10 μmol/L) of product 2h

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无金属参与下不饱和酰胺与多氯甲烷的串联环化反应

Metal-Free-Involved Cascade Cyclization of Unsaturated Amides with Polychloromethanes

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