Electrochemical Oxidative Deaminative Cyclization for the Synthesis of Quinazolines

doi:10.6023/cjoc202512006

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2358-2368.DOI: 10.6023/cjoc202512006 Previous Articles Next Articles

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电化学氧化脱氨环化反应合成喹唑啉

吴际伟^a^,^b^,^*(), 张迪^a, 梅睿^a, 周慧乔^a, 汪洪湖^b, 段小瑞^b, 李子荣^a^,^*()

^a 安徽科技学院化学与材料工程学院安徽凤阳 233100
^b 安徽泰格生物科技有限公司安徽蚌埠 233000

收稿日期:2025-12-04 修回日期:2026-02-28 发布日期:2026-04-20
基金资助:
安徽省高等学科学研究(2024AH050319); 安徽省应用型高峰培育学科(XK-XJGF005); 安徽科技学人才引进(HCYJ201903); 国家级大学生创新创业训练计划(202410879034); 国家级大学生创新创业训练计划(202510879023); 南京博衢化工有限公司(881527)

Electrochemical Oxidative Deaminative Cyclization for the Synthesis of Quinazolines

Jiwei Wu^a^,^b^,^*(), Di Zhang^a, Rui Mei^a, Huiqiao Zhou^a, Honghu Wang^b, Xiaorui Duan^b, Zirong Li^a^,^*()

^a College of Chemistry and Materials Engineering, Anhui Science and Technology University, Fengyang, Anhui 233100
^b Anhui Taige Biotech Co., Ltd., Bengbu, Anhui 233000

Received:2025-12-04 Revised:2026-02-28 Published:2026-04-20
Contact: * E-mail: wujw@ahstu.edu.cn;lizir@ahstu.edu.cn
Supported by:
Natural Science Research Project of Anhui Educational Committee(2024AH050319); Anhui Province Applied Peak Cultivation Discipline(XK-XJGF005); Anhui Science and Technology Talent Introduction Project(HCYJ201903); Innovation and Entrepreneurship Training Program for College Students(202410879034); Innovation and Entrepreneurship Training Program for College Students(202510879023); Nanjing Boqu Chemical Co., Ltd(881527)

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Abstract

An electrochemical method for the synthesis of quinazoline heterocycles without the need for external oxidants or transition-metal has been developed. In an undivided electrochemical cell, using ammonium iodide as the electrolyte, readily available graphite rods and nickel plates as the anode and cathode, a series of biologically active quinazoline derivatives were efficiently synthesized. This strategy exhibits excellent functional group compatibility, accommodating various substituted benzylamines including electron-donating groups, electron-withdrawing groups, halogens and heterocycles. The protocol was successfully extended to 2-amino-2-arylacetic acids as substrates, with 2-amino-2-phenylacetic acid affording the corres- ponding product in 45%~98% yields under optimized conditions.

Key words: electrochemistry, oxidative annulation, quinazolines

Cite this article

Jiwei Wu, Di Zhang, Rui Mei, Huiqiao Zhou, Honghu Wang, Xiaorui Duan, Zirong Li. Electrochemical Oxidative Deaminative Cyclization for the Synthesis of Quinazolines[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2358-2368.

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Fig. & Tab. 10

References 26

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Entry	Anode/Cathode	Electrolyte/mmol	Solvent	Current/mA	Temp./℃	Yield^b/%
1	C(+)/Ni(–)	ⁿBu₄NBF₄ (1.0)	CH₃CN	10	80	6
2	C(+)/Ni(–)	ⁿBu₄NPF₆ (1.0)	CH₃CN	10	80	Trace
3	C(+)/Ni(–)	Et₄NBF₄ (1.0)	CH₃CN	10	80	Trace
4	C(+)/Ni(–)	ⁿBu₄NBr (1.0)	CH₃CN	10	80	Trace
5	C(+)/Ni(–)	ⁿBu₄NI (1.0)	CH₃CN	10	80	7
6	C(+)/Ni(–)	NH₄I (1.0)	CH₃CN	10	80	14
7	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	80	25
8	C(+)/Ni(–)	NH₄I (1.0)	DMF	10	80	11
9	C(+)/Ni(–)	NH₄I (1.0)	EtOH	10	80	Trace
10	C(+)/Ni(–)	NH₄I (1.0)	THF	10	80	Trace
11	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	100	30
12	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	120	38
13	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	130	38
14	C(+)/Ni(–)	NH₄I (1.0)	DMSO	15	120	61
15	C(+)/Ni(–)	NH₄I (1.0)	DMSO	20	120	72
16	C(+)/Ni(–)	NH₄I (1.0)	DMSO	25	120	66
17	C(+)/Pt(–)	NH₄I (1.0)	DMSO	20	120	59
18	C(+)/C(–)	NH₄I (1.0)	DMSO	20	120	42
19	Pt(+)/Pt(–)	NH₄I (1.0)	DMSO	20	120	33
20^c	C(+)/Ni(–)	NH₄I (1.0)	DMSO	20	120	80
21	C(+)/Ni(–)	NH₄I (0.5)	DMSO	20	120	79
22	C(+)/Ni(–)	NH₄I (0.4)	DMSO	20	120	72
23^d	C(+)/Ni(–)	NH₄I (0.5)	DMSO	20	120	79
24	C(+)/Ni(–)	NH₄I (0.5)	DMSO	0	120	0

Entry	Anode/Cathode	Electrolyte/mmol	Solvent	Current/mA	Temp./℃	Yield^b/%
1	C(+)/Ni(–)	ⁿBu₄NBF₄ (1.0)	CH₃CN	10	80	6
2	C(+)/Ni(–)	ⁿBu₄NPF₆ (1.0)	CH₃CN	10	80	Trace
3	C(+)/Ni(–)	Et₄NBF₄ (1.0)	CH₃CN	10	80	Trace
4	C(+)/Ni(–)	ⁿBu₄NBr (1.0)	CH₃CN	10	80	Trace
5	C(+)/Ni(–)	ⁿBu₄NI (1.0)	CH₃CN	10	80	7
6	C(+)/Ni(–)	NH₄I (1.0)	CH₃CN	10	80	14
7	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	80	25
8	C(+)/Ni(–)	NH₄I (1.0)	DMF	10	80	11
9	C(+)/Ni(–)	NH₄I (1.0)	EtOH	10	80	Trace
10	C(+)/Ni(–)	NH₄I (1.0)	THF	10	80	Trace
11	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	100	30
12	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	120	38
13	C(+)/Ni(–)	NH₄I (1.0)	DMSO	10	130	38
14	C(+)/Ni(–)	NH₄I (1.0)	DMSO	15	120	61
15	C(+)/Ni(–)	NH₄I (1.0)	DMSO	20	120	72
16	C(+)/Ni(–)	NH₄I (1.0)	DMSO	25	120	66
17	C(+)/Pt(–)	NH₄I (1.0)	DMSO	20	120	59
18	C(+)/C(–)	NH₄I (1.0)	DMSO	20	120	42
19	Pt(+)/Pt(–)	NH₄I (1.0)	DMSO	20	120	33
20^c	C(+)/Ni(–)	NH₄I (1.0)	DMSO	20	120	80
21	C(+)/Ni(–)	NH₄I (0.5)	DMSO	20	120	79
22	C(+)/Ni(–)	NH₄I (0.4)	DMSO	20	120	72
23^d	C(+)/Ni(–)	NH₄I (0.5)	DMSO	20	120	79
24	C(+)/Ni(–)	NH₄I (0.5)	DMSO	0	120	0

电化学氧化脱氨环化反应合成喹唑啉

Electrochemical Oxidative Deaminative Cyclization for the Synthesis of Quinazolines

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