One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]-quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction

doi:10.6023/cjoc202005029

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 297-302.DOI: 10.6023/cjoc202005029 Previous Articles Next Articles

Article

无金属参与的连续的Ugi三组分/炔烃-叠氮环加成反应一锅合成[1,2,3]三唑并[1,5- a]喹喔啉

石瑛^a, 秦富文^c, 王捷^a, 闫艳梅^b^,^*()

a 太原师范学院生物系山西晋中 030619
b 太原师范学院化学系山西晋中 030619
c 山西大学化学化工学院山西太原 030006

收稿日期:2020-05-13 修回日期:2020-07-27 发布日期:2020-09-09
通讯作者: 闫艳梅
作者简介:
* Corresponding author. E-mail: yanyanmei1019@yeah.net
基金资助:
山西省“1331工程”重点创新团队建设计划(TD201718); 山西省重点研发计划(201803D31054); 山西省应用基础研究计划面上青年(201901D211422); 山西省高等学校科技创新(2019L0775)

One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]-quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction

Ying Shi^a, Fuwen Qin^c, Jie Wang^a, Yanmei Yan^b^,^*()

a Department of Biology, Taiyuan Normal University, Jinzhong, Shanxi 030619
b Department of Chemistry, Taiyuan Normal University, Jinzhong, Shanxi 030619
c School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, Shanxi 030006

Received:2020-05-13 Revised:2020-07-27 Published:2020-09-09
Contact: Yanmei Yan
Supported by:
the Fund for Shanxi “1331 Project” Key Innovative Research Team(TD201718); the Key Research and Development Projects of Shanxi Province(201803D31054); the Science Foundation for Youths of Shanxi Province(201901D211422); the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province(2019L0775)

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Abstract

A new one-pot metal-free preparation of [1,2,3]triazolo[1,5- a]quinoxalines by a Ugi-3CR/alkyne-azide cycloaddition sequence has been developed. The reaction of 2-azidobenzenamines, propiolic aldehydes and isocyanides produced [1,2,3]triazolo[1,5- a]quinoxalines in 55%~85% yields via sequential Ugi-3CR/alkyne-azide cycloaddition reaction in the presence of H₃PO₄ and heating in toluene respectively.

Key words: one-pot, metal-free, [1,2,3]triazolo[1,5-a]quinoxaline, Ugi-3CR, alkyne-azide cycloaddition

Cite this article

Ying Shi, Fuwen Qin, Jie Wang, Yanmei Yan. One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]-quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 297-302.

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Fig. & Tab. 4

References 19

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Entry	Catalyst (mol%)	Solvent 2	Temp./℃	Yield ^a /%
1	—	MeOH	r.t.	0
2	H ₃PO ₄ (20)	MeOH	r.t.	0
3	H ₃PO ₄ (20)	MeOH	65	0
4	H ₃ PO ₄ (20)	Toluene	80	70
5	H ₃PO ₄ (20)	DMF	80	68
6	H ₃PO ₄ (20)	DMSO	80	65
7	H ₃PO ₄ (20)	1,4-Dioxane	80	55
8	H ₃PO ₄ (10)	Toluene	80	45
9	H ₂SO ₄ (20)	Toluene	80	40
10	HCl (20)	Toluene	80	50
11	HNO ₃(20)	Toluene	80	55
12	TsOH (20)	Toluene	80	50
13	CF ₃SO ₃H (20)	Toluene	80	67
14	CH ₃COOH (20)	Toluene	80	56
15	PhCOOH (20)	Toluene	80	0
16	(20)	Toluene	80	0
17	AlCl ₃ (20)	Toluene	80	0
18	ZnCl ₂ (20)	Toluene	80	0
19	FeCl ₂ (20)	Toluene	80	0
20	MgSO ₄ (20)	Toluene	80	0
21	FeCl ₃ (20)	Toluene	80	0

Entry	Catalyst (mol%)	Solvent 2	Temp./℃	Yield ^a /%
1	—	MeOH	r.t.	0
2	H ₃PO ₄ (20)	MeOH	r.t.	0
3	H ₃PO ₄ (20)	MeOH	65	0
4	H ₃ PO ₄ (20)	Toluene	80	70
5	H ₃PO ₄ (20)	DMF	80	68
6	H ₃PO ₄ (20)	DMSO	80	65
7	H ₃PO ₄ (20)	1,4-Dioxane	80	55
8	H ₃PO ₄ (10)	Toluene	80	45
9	H ₂SO ₄ (20)	Toluene	80	40
10	HCl (20)	Toluene	80	50
11	HNO ₃(20)	Toluene	80	55
12	TsOH (20)	Toluene	80	50
13	CF ₃SO ₃H (20)	Toluene	80	67
14	CH ₃COOH (20)	Toluene	80	56
15	PhCOOH (20)	Toluene	80	0
16	(20)	Toluene	80	0
17	AlCl ₃ (20)	Toluene	80	0
18	ZnCl ₂ (20)	Toluene	80	0
19	FeCl ₂ (20)	Toluene	80	0
20	MgSO ₄ (20)	Toluene	80	0
21	FeCl ₃ (20)	Toluene	80	0

Entry	5	R ¹	R ²	R ³	Yield ^a /%
1	5a	H	Ph	t-Bu	70
2	5b	H	Ph	c-C ₆H ₁₁	71
3	5c	4-CH ₃	Si(CH ₃) ₃	t-Bu	85
4	5d	4-Cl	Ph	t-Bu	65
5	5e	4-Cl	Ph	c-C ₆H ₁₁	67
6	5f	4-Br	Ph	t-Bu	62
7	5g	4-Br	Ph	c-C ₆H ₁₁	63
8	5h	H	Si(CH ₃) ₃	t-Bu	80
9	5i	H	Si(CH ₃) ₃	c-C ₆H ₁₁	81
10	5j	4-Cl	Si(CH ₃) ₃	t-Bu	75
11	5k	4-Br	Si(CH ₃) ₃	t-Bu	70
12	5l	H	CH ₃(CH ₂) ₄	t-Bu	68
13	5m	4-Cl	CH ₃(CH ₂) ₄	t-Bu	60
14	5n	H	Ph	n-Bu	74
15	5o	H	Ph	Benzyl	55
16	5p	H	Ph	Ph	0
17	5q	3-Br	Ph	t-Bu	0
18	5r	3-CH ₃	Ph	t-Bu	0
19	5s	4,6-(CH ₃) ₂	Ph	t-Bu	0

Entry	5	R ¹	R ²	R ³	Yield ^a /%
1	5a	H	Ph	t-Bu	70
2	5b	H	Ph	c-C ₆H ₁₁	71
3	5c	4-CH ₃	Si(CH ₃) ₃	t-Bu	85
4	5d	4-Cl	Ph	t-Bu	65
5	5e	4-Cl	Ph	c-C ₆H ₁₁	67
6	5f	4-Br	Ph	t-Bu	62
7	5g	4-Br	Ph	c-C ₆H ₁₁	63
8	5h	H	Si(CH ₃) ₃	t-Bu	80
9	5i	H	Si(CH ₃) ₃	c-C ₆H ₁₁	81
10	5j	4-Cl	Si(CH ₃) ₃	t-Bu	75
11	5k	4-Br	Si(CH ₃) ₃	t-Bu	70
12	5l	H	CH ₃(CH ₂) ₄	t-Bu	68
13	5m	4-Cl	CH ₃(CH ₂) ₄	t-Bu	60
14	5n	H	Ph	n-Bu	74
15	5o	H	Ph	Benzyl	55
16	5p	H	Ph	Ph	0
17	5q	3-Br	Ph	t-Bu	0
18	5r	3-CH ₃	Ph	t-Bu	0
19	5s	4,6-(CH ₃) ₂	Ph	t-Bu	0

无金属参与的连续的Ugi三组分/炔烃-叠氮环加成反应一锅合成[1,2,3]三唑并[1,5- a]喹喔啉

One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]-quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction

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