叔丁基过氧化氢促进喹喔啉酮、N-芳基甘氨酸和多聚甲醛的三组分反应: 高效合成四氢咪唑并[1,5-a]喹喔啉酮

doi:10.6023/cjoc202601030

有机化学 ›› 2026, Vol. 46 ›› Issue (4): 1668-1676.DOI: 10.6023/cjoc202601030 上一篇下一篇

研究论文

叔丁基过氧化氢促进喹喔啉酮、N-芳基甘氨酸和多聚甲醛的三组分反应: 高效合成四氢咪唑并[1,5-a]喹喔啉酮

李婷^a, 欧阳文韬^a, 易荣楠^b^,^*(), 唐欲才^c, 杨梓^d^,^*(), 吴超^a^,^*(), 何卫民^a^,^*()

^a 南华大学化学化工学院湖南衡阳 421001
^b 湖南警察学院食药环及毒品检验技术湖南省普通高等学校重点实验室食药环及毒品检验技术湖南省普通高等学校重点实验室长沙 410138
^c 湖南文理学院化学与材料工程学院湖南常德 415000
^d 长沙医学院功能核酸基础与临床湖南省普通高校重点实验室功能核酸基础与临床湖南省普通高校重点实验室长沙 410219

收稿日期:2026-01-20 修回日期:2026-03-31 发布日期:2026-04-13
通讯作者: 易荣楠, 杨梓, 吴超, 何卫民
基金资助:
湖南省自然科学基金(2026JJ90135); 湖南省教育厅科学研究(25A0703); 长沙市自然科学基金(104872)

t-Butyl Hydroperoxide-Promoted Three-Component Reaction of Quinoxalin-2(1H)-ones, N-Phenylglycines and Paraformaldehyde: an Efficient Approach to Tetrahydroimidazo-[1,5-a]quinoxalin-4(5H)-ones

Ting Li^a, Wentao Ouyang^a, Rongnan Yi^b^,^*(), Yucai Tang^c, Zi Yang^d^,^*(), Chao Wu^a^,^*(), Weimin He^a^,^*()

^a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
^b Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138
^c College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000
^d Hunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219

Received:2026-01-20 Revised:2026-03-31 Published:2026-04-13
Contact: Rongnan Yi, Zi Yang, Chao Wu, Weimin He
Supported by:
Hunan Provincial Natural Science Foundation(2026JJ90135); Scientific Research Fund of Hunan Provincial Education Department(25A0703); Changsha Natural Science Foundation(104872)

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摘要/Abstract

喹喔啉酮类化合物的C3位官能团化衍生物通常具有良好的生物活性和药理价值. 目前, 通过C3—H官能团化策略, 研究人员成功合成了一系列在3位引入烷基、芳基、氨基、氟烷基、酰基及磷酰基等基团的喹喔啉酮衍生物. 然而, 基于喹喔啉酮C3—H活化的串联环化反应, 用于构建含喹喔啉酮骨架的稠合杂环化合物的报道仍相对有限. 此研究以廉价易得的过氧叔丁醇为氧化剂、多聚甲醛为C1合成子, 发展了一种高效的多组分合成方法, 成功合成了一系列四氢咪唑并[1,5-a]喹喔啉-4(5H)-酮类化合物. 该反应无需特殊装置, 可在空气氛围中进行, 具有反应条件温和、操作简便和成本低廉等优点, 有望成为合成四氢咪唑并喹喔啉酮类化合物的一种实用策略.

关键词: 喹喔啉-2(1H)-酮, N-芳基甘氨酸, 多聚甲醛, 脱羧, 串联反应

C3-Functionalized quinoxalin-2(1H)-ones generally exhibit promising biological activities and pharmacological values. Currently, a series of C3-functionalized quinoxalin-2(1H)-ones bearing alkyl, aryl, amino, fluoroalkyl, acyl, and phosphoryl groups have been synthesized through the C3—H functionalization strategy. However, reports on the construction of fused-heterocycles incorporating a quinoxalinone skeleton via a cascade cyclization reaction initiated by C3—H activation remain relatively limited. Herein, an efficient multi-component synthetic protocol was reported using low-cost, readily available t-butyl hydroperoxide as the oxidant and paraformaldehyde as the C1 synthon, enabling the synthesis of a series of tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones. This reaction proceeds without the need for special apparatus under ambient air, featuring mild conditions, simple operation, and low cost. This strategy holds great potential as a practical approach for the synthesis of tetrahydroimidazoquinoxalinone compounds.

Key words: quinoxalin-2(1H)-ones, N-phenylglycines, paraformaldehyde, decarboxylation, cyclization reaction

引用此文

李婷, 欧阳文韬, 易荣楠, 唐欲才, 杨梓, 吴超, 何卫民. 叔丁基过氧化氢促进喹喔啉酮、N-芳基甘氨酸和多聚甲醛的三组分反应: 高效合成四氢咪唑并[1,5-a]喹喔啉酮[J]. 有机化学, 2026, 46(4): 1668-1676.

Ting Li, Wentao Ouyang, Rongnan Yi, Yucai Tang, Zi Yang, Chao Wu, Weimin He. t-Butyl Hydroperoxide-Promoted Three-Component Reaction of Quinoxalin-2(1H)-ones, N-Phenylglycines and Paraformaldehyde: an Efficient Approach to Tetrahydroimidazo-[1,5-a]quinoxalin-4(5H)-ones[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1668-1676.

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Entry	Oxidant	Solvent (V/V)	Temp./℃	Yield^b/%
1	H₂O₂	EtOH/H₂O (2/1)	80	45
2	TBHP	EtOH/H₂O (2/1)	80	83 (78)
3	DTBP	EtOH/H₂O (2/1)	80	37
4	BPO	EtOH/H₂O (2/1)	80	31
5	K₂S₂O₈	EtOH/H₂O (2/1)	80	49
6^c	TBHP	EtOH/H₂O (2/1)	80	58
7	w/o	EtOH/H₂O (2/1)	80	Trace
8	TBHP	EtOH	80	59
9	TBHP	H₂O	80	42
10	TBHP	EtOH/H₂O (3/1)	80	74
11	TBHP	EtOH/H₂O (1/1)	80	63
12	TBHP	Acetone/H₂O (2/1)	80	23
13	TBHP	DMSO/H₂O (2/1)	80	35
14	TBHP	DMF/H₂O (2/1)	80	26
15	TBHP	MeCN/H₂O (2/1)	80	39
16	TBHP	THF/H₂O (2/1)	80	Trace
17	TBHP	EtOH/H₂O (2/1)	70	63
18	TBHP	EtOH/H₂O (2/1)	r.t.	17
19	TBHP	EtOH/H₂O (2/1)	90	82

Entry	Oxidant	Solvent (V/V)	Temp./℃	Yield^b/%
1	H₂O₂	EtOH/H₂O (2/1)	80	45
2	TBHP	EtOH/H₂O (2/1)	80	83 (78)
3	DTBP	EtOH/H₂O (2/1)	80	37
4	BPO	EtOH/H₂O (2/1)	80	31
5	K₂S₂O₈	EtOH/H₂O (2/1)	80	49
6^c	TBHP	EtOH/H₂O (2/1)	80	58
7	w/o	EtOH/H₂O (2/1)	80	Trace
8	TBHP	EtOH	80	59
9	TBHP	H₂O	80	42
10	TBHP	EtOH/H₂O (3/1)	80	74
11	TBHP	EtOH/H₂O (1/1)	80	63
12	TBHP	Acetone/H₂O (2/1)	80	23
13	TBHP	DMSO/H₂O (2/1)	80	35
14	TBHP	DMF/H₂O (2/1)	80	26
15	TBHP	MeCN/H₂O (2/1)	80	39
16	TBHP	THF/H₂O (2/1)	80	Trace
17	TBHP	EtOH/H₂O (2/1)	70	63
18	TBHP	EtOH/H₂O (2/1)	r.t.	17
19	TBHP	EtOH/H₂O (2/1)	90	82

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