Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO2/Na2S2O8-Mediated Arylnitration of Alkenes

doi:10.6023/cjoc202010014

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1734-1738.DOI: 10.6023/cjoc202010014 Previous Articles Next Articles

NOTES

NaNO₂/Na₂S₂O₈介导烯烃硝芳化反应合成硝基异喹啉二酮研究

张玲玲^a^,^*(), 王知^b, 吴剑^a, 李小青^b^,^*()

a 江苏环保产业技术研究院股份公司南京 210019
b 浙江工业大学化学工程学院杭州 310014

收稿日期:2020-10-11 修回日期:2020-11-13 发布日期:2020-12-05
通讯作者: 张玲玲, 李小青

Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO₂/Na₂S₂O₈-Mediated Arylnitration of Alkenes

Lingling Zhang^a^,^*(), Zhi Wang^b, Jian Wu^a, Xiaoqing Li^b^,^*()

a Jiangsu Academy of Environmental Industry and Technology Corp., Nanjing 210019
b College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2020-10-11 Revised:2020-11-13 Published:2020-12-05
Contact: Lingling Zhang, Xiaoqing Li
About author:
* Corresponding authors. E-mail: veronica_zll@126.com;
E-mail: xqli@zjut.edu.cn

1. cjoc202010014辅助材料.pdf(1225KB)

Abstract

A new method for the synthesis of nitro-functionalized isoquinolinediones by arylnitration of methacryloylbenzamides has been reported. Readily accessible NaNO₂/Na₂S₂O₈ was used as nitro radical precursor, and 18-crown-6 was used to promote the reaction. Compared with the existing method, this method is not only environmentally friendly but also easy to operate.

Key words: Keywords alkenes, arylnitration, cyclization, nitro radical, isoquinolinediones

Cite this article

Lingling Zhang, Zhi Wang, Jian Wu, Xiaoqing Li. Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO₂/Na₂S₂O₈-Mediated Arylnitration of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1734-1738.

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References 13

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Entry	Solvent	Oxidant	Temp./℃	Yield^b/%
1^c	MeCN	K₂S₂O₈	120	22
2	MeCN	K₂S₂O₈	120	48
3	1,4-Dioxane	K₂S₂O₈	120	50
4	DCE	K₂S₂O₈	120	24
5	DMF	K₂S₂O₈	120	18
6	DMSO	K₂S₂O₈	120	21
7	1,4-Dioxane	Na₂S₂O₈	120	60
8	1,4-Dioxane	(NH₄)₂S₂O₈	120	56
9	1,4-Dioxane	TBHP	120	18
10	1,4-Dioxane	Na₂S₂O₈	110	53
11	1,4-Dioxane	Na₂S₂O₈	130	56
12^d	1,4-Dioxane	Na₂S₂O₈	120	58

Entry	Solvent	Oxidant	Temp./℃	Yield^b/%
1^c	MeCN	K₂S₂O₈	120	22
2	MeCN	K₂S₂O₈	120	48
3	1,4-Dioxane	K₂S₂O₈	120	50
4	DCE	K₂S₂O₈	120	24
5	DMF	K₂S₂O₈	120	18
6	DMSO	K₂S₂O₈	120	21
7	1,4-Dioxane	Na₂S₂O₈	120	60
8	1,4-Dioxane	(NH₄)₂S₂O₈	120	56
9	1,4-Dioxane	TBHP	120	18
10	1,4-Dioxane	Na₂S₂O₈	110	53
11	1,4-Dioxane	Na₂S₂O₈	130	56
12^d	1,4-Dioxane	Na₂S₂O₈	120	58

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NaNO₂/Na₂S₂O₈介导烯烃硝芳化反应合成硝基异喹啉二酮研究

Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO₂/Na₂S₂O₈-Mediated Arylnitration of Alkenes

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NaNO2/Na2S2O8介导烯烃硝芳化反应合成硝基异喹啉二酮研究