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

doi:10.6023/cjoc202102035

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3106-3115.DOI: 10.6023/cjoc202102035 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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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

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

Substrate 1	Product 2	Substrate 1	Product 2

Substrate 1	Product 2	Substrate 1	Product 2

Substrate 1	Product 3	Substrate 1	Product 3

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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