A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates

doi:10.6023/cjoc202012007

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1982-1990.DOI: 10.6023/cjoc202012007 Previous Articles Next Articles

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铜(I)催化邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯串联双环化反应快速合成5H-苯并咪唑[5,1-b][1,3]噻嗪

张亚辉¹, 吴文锦¹, 张可心¹, 黎双双¹, 郝文燕¹^,^*()

1 江西师范大学化学与化工学院功能有机小分子教育部重点实验室江西省绿色化学重点实验室南昌 330022

收稿日期:2020-12-02 修回日期:2021-01-18 发布日期:2021-02-22
通讯作者: 郝文燕
基金资助:
国家自然科学基金(21762023); 国家自然科学基金(22061021); 江西省自然科学基金(2018BAB203006)

A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates

Yahui Zhang¹, Wenjin Wu¹, Kexin Zhang¹, Shuangshuang Li¹, Wenyan Hao¹^,^*()

1 Key Laboratory of Functional Small Organic Molecules of Ministry of Education, Jiangxi Key Laboratory of Green Chemistry, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received:2020-12-02 Revised:2021-01-18 Published:2021-02-22
Contact: Wenyan Hao
About author:
* Corresponding author. E-mail: wenyanhao@jxnu.edu.cn
Supported by:
National Natural Science Foundation of China(21762023); National Natural Science Foundation of China(22061021); Natural Science Foundation of Jiangxi Province(2018BAB203006)

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Abstract

A rapid and efficient protocol for copper(I)-catalyzed tandem bicyclization of o-alkynylphenyl isothiocyanates with ethyl (E)-2-(benzylideneamino)acetates has been developed, affording a series of 5H-benzo[d]imidazo[5,1-b][1,3]thia- zines in moderate to good yields. In this transformation, a [3+2] cycloaddition reaction mechanism was involved and two new rings were formed in one pot.

Key words: Keywords copper-catalysis, cascade bicyclization, 5H-benzo[d]imidazo[5,1-b][1,3]thiazine

Cite this article

Yahui Zhang, Wenjin Wu, Kexin Zhang, Shuangshuang Li, Wenyan Hao. A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1982-1990.

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Entry	Catalyst	Base	Solvent	Temp./℃	Yield^b/%
1	Cu(OAc)₂	Cs₂CO₃	MeCN	80	40
2	Cu(OTf)₂	Cs₂CO₃	MeCN	80	36
3	CuBr₂	Cs₂CO₃	MeCN	80	42
4	CuO	Cs₂CO₃	MeCN	80	47
5	CuI	Cs₂CO₃	MeCN	80	42
6	CuBr	Cs₂CO₃	MeCN	80	47
7	CuCl	Cs₂CO₃	MeCN	80	52
8		Cs₂CO₃	MeCN	80	30
9	CuCl		MeCN	80	32
10^c	CuCl	Cs₂CO₃	MeCN	80	53
11^c	CuCl	K₃PO₄	MeCN	80	Trace
12^c	CuCl	Na₂HPO₄	MeCN	80	Trace
13^c	CuCl	K₂CO₃	MeCN	80	53
14^c	CuCl	Na₂CO₃	MeCN	80	56
15^c	CuCl	NaOH	MeCN	80	79
16^c	CuCl	KOH	MeCN	80	81
17^c	CuCl	t-BuOK	MeCN	80	65
18^c	CuCl	DBU	MeCN	80	70
19^c	CuCl	KOH	DCE	80	37
20^c	CuCl	KOH	Toluene	80	44
21^c	CuCl	KOH	1,4-Dioxane	80	33
22^c	CuCl	KOH	THF	80	40
23^c	CuCl	KOH	CH₃OH	80	36
24^c	CuCl	KOH	DMF	80	56
25^c	CuCl	KOH	DMSO	80	62
26^c	CuCl	KOH	MeCN	120	Trace
27^c	CuCl	KOH	MeCN	100	66
28^c	CuCl	KOH	MeCN	60	77
29^c	CuCl	KOH	MeCN	40	79
30^c	CuCl	KOH	MeCN	25	83

Entry	Catalyst	Base	Solvent	Temp./℃	Yield^b/%
1	Cu(OAc)₂	Cs₂CO₃	MeCN	80	40
2	Cu(OTf)₂	Cs₂CO₃	MeCN	80	36
3	CuBr₂	Cs₂CO₃	MeCN	80	42
4	CuO	Cs₂CO₃	MeCN	80	47
5	CuI	Cs₂CO₃	MeCN	80	42
6	CuBr	Cs₂CO₃	MeCN	80	47
7	CuCl	Cs₂CO₃	MeCN	80	52
8		Cs₂CO₃	MeCN	80	30
9	CuCl		MeCN	80	32
10^c	CuCl	Cs₂CO₃	MeCN	80	53
11^c	CuCl	K₃PO₄	MeCN	80	Trace
12^c	CuCl	Na₂HPO₄	MeCN	80	Trace
13^c	CuCl	K₂CO₃	MeCN	80	53
14^c	CuCl	Na₂CO₃	MeCN	80	56
15^c	CuCl	NaOH	MeCN	80	79
16^c	CuCl	KOH	MeCN	80	81
17^c	CuCl	t-BuOK	MeCN	80	65
18^c	CuCl	DBU	MeCN	80	70
19^c	CuCl	KOH	DCE	80	37
20^c	CuCl	KOH	Toluene	80	44
21^c	CuCl	KOH	1,4-Dioxane	80	33
22^c	CuCl	KOH	THF	80	40
23^c	CuCl	KOH	CH₃OH	80	36
24^c	CuCl	KOH	DMF	80	56
25^c	CuCl	KOH	DMSO	80	62
26^c	CuCl	KOH	MeCN	120	Trace
27^c	CuCl	KOH	MeCN	100	66
28^c	CuCl	KOH	MeCN	60	77
29^c	CuCl	KOH	MeCN	40	79
30^c	CuCl	KOH	MeCN	25	83

铜(I)催化邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯串联双环化反应快速合成5H-苯并咪唑[5,1-b][1,3]噻嗪

A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates

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