Electrochemistry-Enabled Copper-Catalyzed Oxidation of Benzyl Alcohols for the Preparation of Quinazolinones in Water

doi:10.6023/cjoc202012028

Abstract

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

Cite this article

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

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