水相中电化学促进铜催化苯甲醇氧化合成喹唑啉酮

doi:10.6023/cjoc202012028

摘要/Abstract

喹唑啉酮类化合物是一种重要的含氮杂环化合物, 也是多种天然产物以及合成药物的骨架分子. 利用廉价易得的苯甲醇以及邻氨基苯甲酰胺为原料, 通过CuCl₂和电流共同氧化苯甲醇, 在室温条件下于水相中一锅法合成喹唑啉酮及其衍生物, 目标化合物可获得中等至优秀的产率. 该方法用电流代替价格昂贵、毒性大的氧化剂, 为合成喹唑啉酮类化合物提供了一条操作简便、绿色可持续的合成途径.

关键词: 电合成, 喹唑啉酮, 绿色化学, 铜催化剂, 水相

Quinazolinone is one of the most important nitrogen-containing heterocyclic compound, which is widely found in numerous natural products and synthetic drugs. Quinazolinone derivatives were synthesized by one-pot co-oxidation of benzyl alcohol with CuCl₂ and electric current in aqueous phase. The reaction provides an efficient protocol to a series of quinazolinones derivatives in good to high yields. This synthesis process features convenient operation and environmental friendliness, which make it a promising method for the preparation of quinazolinone derivatives insteading of expensive and toxic oxidants with electric current.

Key words: electrochemistry, quinazolinone, green chemistry, copper catalysis, water

引用此文

吴媚, 于玲, 侯慧青, 陈厚铮, 庄庆龙, 周孙英, 林小燕. 水相中电化学促进铜催化苯甲醇氧化合成喹唑啉酮[J]. 有机化学, 2021, 41(6): 2326-2334.

Mei Wu, Ling Yu, Huiqing Hou, Houzheng Chen, Qinglong Zhuang, Sunying Zhou, Xiaoyan Lin. Electrochemistry-Enabled Copper-Catalyzed Oxidation of Benzyl Alcohols for the Preparation of Quinazolinones in Water[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2326-2334.

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Entry	Solvent	Cat.	Base	Current/ mA	t/h	Electrode	Yield^b/ %
1	CH₃CN	CuCl₂	NaOH	40	12	Pt-Pt	51
2	DMSO	CuCl₂	NaOH	40	12	Pt-Pt	72
3	DMF	CuCl₂	NaOH	40	12	Pt-Pt	60
4	Toluene	CuCl₂	NaOH	40	12	Pt-Pt	80
5	H₂O	CuCl₂	NaOH	40	12	Pt-Pt	91
6	H₂O	CuSO₄	NaOH	40	12	Pt-Pt	53
7	H₂O	Cu(OAc)₂	NaOH	40	12	Pt-Pt	67
8	H₂O	Cu(NO₃)₂	NaOH	40	12	Pt-Pt	57
9	H₂O	—	NaOH	40	12	Pt-Pt	Trace
10	H₂O	CuCl₂	K₂CO₃	40	12	Pt-Pt	51
11	H₂O	CuCl₂	Cs₂CO₃	40	12	Pt-Pt	66
12	H₂O	CuCl₂	KOH	40	12	Pt-Pt	72
13	H₂O	CuCl₂	—	40	12	Pt-Pt	Trace
14	H₂O	CuCl₂	NaOH	30	12	Pt-Pt	82
15	H₂O	CuCl₂	NaOH	50	12	Pt-Pt	68
16^c	H₂O	CuCl₂	NaOH	—	12	Pt-Pt	Trace
17	H₂O	CuCl₂	NaOH	40	11	Pt-Pt	84
18	H₂O	CuCl₂	NaOH	40	13	Pt-Pt	91
19	H₂O	CuCl₂	NaOH	40	12	Pt-C	86
20	H₂O	CuCl₂	NaOH	40	12	Pt-Ag	79
21^d	H₂O	CuCl₂	NaOH	40	12	Pt-Pt	90

Entry	Solvent	Cat.	Base	Current/ mA	t/h	Electrode	Yield^b/ %
1	CH₃CN	CuCl₂	NaOH	40	12	Pt-Pt	51
2	DMSO	CuCl₂	NaOH	40	12	Pt-Pt	72
3	DMF	CuCl₂	NaOH	40	12	Pt-Pt	60
4	Toluene	CuCl₂	NaOH	40	12	Pt-Pt	80
5	H₂O	CuCl₂	NaOH	40	12	Pt-Pt	91
6	H₂O	CuSO₄	NaOH	40	12	Pt-Pt	53
7	H₂O	Cu(OAc)₂	NaOH	40	12	Pt-Pt	67
8	H₂O	Cu(NO₃)₂	NaOH	40	12	Pt-Pt	57
9	H₂O	—	NaOH	40	12	Pt-Pt	Trace
10	H₂O	CuCl₂	K₂CO₃	40	12	Pt-Pt	51
11	H₂O	CuCl₂	Cs₂CO₃	40	12	Pt-Pt	66
12	H₂O	CuCl₂	KOH	40	12	Pt-Pt	72
13	H₂O	CuCl₂	—	40	12	Pt-Pt	Trace
14	H₂O	CuCl₂	NaOH	30	12	Pt-Pt	82
15	H₂O	CuCl₂	NaOH	50	12	Pt-Pt	68
16^c	H₂O	CuCl₂	NaOH	—	12	Pt-Pt	Trace
17	H₂O	CuCl₂	NaOH	40	11	Pt-Pt	84
18	H₂O	CuCl₂	NaOH	40	13	Pt-Pt	91
19	H₂O	CuCl₂	NaOH	40	12	Pt-C	86
20	H₂O	CuCl₂	NaOH	40	12	Pt-Ag	79
21^d	H₂O	CuCl₂	NaOH	40	12	Pt-Pt	90