Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides

doi:10.6023/cjoc202104047

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3083-3088.DOI: 10.6023/cjoc202104047 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

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可见光诱导的2-(苄基氨基)苯甲酰胺合成4(3H)-喹唑啉酮

李鑫昌^a, 杨惠茹^a, 胡浙耀^a, 金鑫^b, 张文一^c, 郭勋祥^a^,^d^,^*()

a 上海交通大学系统生物医学研究院系统生物医学教育部重点实验室上海 200240
b 上海交通大学化学化工学院上海 200240
c 上海交通大学医学院附属同仁医院上海 200336
d 上海市手性药物分子工程重点实验室上海 200240

收稿日期:2021-04-21 修回日期:2021-04-30 发布日期:2021-05-08
通讯作者: 郭勋祥
基金资助:
上海市科学技术委员会(18JC1410801); 上海交通大学医工交叉基金(YG2019QNA38)

Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides

Xinchang Li^a, Huiru Yang^a, Zheyao Hu^a, Xin Jin^b, Wenyi Zhang^c, Xunxiang Guo^a^,^d()

a Key Laboratory of Systems Biomedicine (Ministry of Education), Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai 200240
b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
c Tongren Hospital, School of Medicine Shanghai Jiao Tong University, Shanghai 200336
d Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai 200240

Received:2021-04-21 Revised:2021-04-30 Published:2021-05-08
Contact: Xunxiang Guo
Supported by:
Science and Technology Commission of Shanghai Municipality(18JC1410801); Medical Engineering Cross Fund of Shanghai Jiao Tong University(YG2019QNA38)

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Abstract

An environmental benign protocol of visible-light-induced reaction has been developed. The methodology allows effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides in simple and mild reaction conditions. Just irradiation with a blue LED light at room temperature, the reaction proceeds well to provide the corresponding quinazolinones in good to high yields under metal-free, photocatalyst-free and mediator-free conditions. This protocol is demonstrated by its wide substrate scope, good functional group tolerance, operationally simple, and gram-scale reaction. Mechanism studies suggest that a radical pathway might be involved in current reaction.

Key words: visible-light, 2-benzylaminobenzamides, 4(3H)-quinazolinones

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Xinchang Li, Huiru Yang, Zheyao Hu, Xin Jin, Wenyi Zhang, Xunxiang Guo. Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3083-3088.

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Fig. & Tab. 7

Scheme 1. Previous works for the synthesis of 4(3H)-quinazo- linones from 2-benzylaminobenzamides (a), and this work (b)

Entry	Variations from standard conditions	Yield^b/%
1	None	88
2	No light	0
3	24 h	38
4	DMF instead of DMSO	3
5	DMA instead of DMSO	9
6	Toluene instead of DMSO	Trace
7	CH₃CN instead of DMSO	4
8	THF instead of DMSO	6
9	Under O₂	87

Table 1. Optimization of the reaction conditionsa

Scheme 2. Scope of substrates 1a~1l

Scheme 3. Scope of substrates 1m~1u

Scheme 4. Gram-scale synthesis of 2a

Scheme 5. Control experiments of the reaction

Scheme 6. Proposal reaction mechanism

References 23

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可见光诱导的2-(苄基氨基)苯甲酰胺合成4(3H)-喹唑啉酮

Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides

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Fig. & Tab. 7

References 23

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