Construction of Quinazolin(thi)ones by Brønsted Acid/Visible-Light Photoredox Relay Catalysis

doi:10.6023/cjoc202206001

Abstract

A relay Brønsted acid/visible-light photoredox catalysis strategy for the synthesis of quinazolin(thi)ones is developed. In this procedure, 2-aminoacetophenones and iso(thio)cyanates undergo Brønsted acid catalyzed [4+2] annulation, followed by photocatalyzed C—C bond cleavage reaction. A wide range of diversely substituted quinazoline-2,4-diones and quinazoline-2-thione-4-ones were synthesized under mild conditions. The protocol features eco-benign energy source and solvent, metal-free catalysts, simple starting materials and air as green oxidant.

Key words: relay catalysis, visible-light catalysis, green synthesis, quinazolinone

Cite this article

Zhentao Pan, Tong Liu, Yongmin Ma, Jianbo Yan, Ya-Jun Wang. Construction of Quinazolin(thi)ones by Brønsted Acid/Visible-Light Photoredox Relay Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2823-2831.

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Entry	Brønsted acid	Photocatalyst	Solvent		Yield^b/%
1	TfOH	Ru(bpz)₃PF₆	DMSO		46
2	TFA	Ru(bpz)₃PF₆	DMSO		53
3	AcOH	Ru(bpz)₃PF₆	DMSO		59
4	H₂SO₄	Ru(bpz)₃PF₆	DMSO		35
5	HNO₃	Ru(bpz)₃PF₆	DMSO		28
6	TsOH	Ru(bpz)₃PF₆	DMSO		63
7	TsOH	Ru(bpm)₃PF₆	DMSO		58
8	TsOH	[Ir(dF(CF₃)ppy)₂dtbbpy]PF₆	DMSO		72
9	TsOH	Mes-Acr-Me⁺ClO₄^–	DMSO		64
Entry	Brønsted acid	Photocatalyst	Solvent	Yield^b/%
10	TsOH	Rose Bengal	DMSO	36
11	TsOH	Eosin Y	DMSO	49
12	TsOH	4CzIPN	DMSO	73
13	TsOH	4CzIPN	DMF	70
14	TsOH	4CzIPN	MeCN	81
15	TsOH	4CzIPN	THF	57
16	TsOH	4CzIPN	CHCl₃	74
17	TsOH	4CzIPN	EtOH	84

Entry	Brønsted acid	Photocatalyst	Solvent		Yield^b/%
1	TfOH	Ru(bpz)₃PF₆	DMSO		46
2	TFA	Ru(bpz)₃PF₆	DMSO		53
3	AcOH	Ru(bpz)₃PF₆	DMSO		59
4	H₂SO₄	Ru(bpz)₃PF₆	DMSO		35
5	HNO₃	Ru(bpz)₃PF₆	DMSO		28
6	TsOH	Ru(bpz)₃PF₆	DMSO		63
7	TsOH	Ru(bpm)₃PF₆	DMSO		58
8	TsOH	[Ir(dF(CF₃)ppy)₂dtbbpy]PF₆	DMSO		72
9	TsOH	Mes-Acr-Me⁺ClO₄^–	DMSO		64
Entry	Brønsted acid	Photocatalyst	Solvent	Yield^b/%
10	TsOH	Rose Bengal	DMSO	36
11	TsOH	Eosin Y	DMSO	49
12	TsOH	4CzIPN	DMSO	73
13	TsOH	4CzIPN	DMF	70
14	TsOH	4CzIPN	MeCN	81
15	TsOH	4CzIPN	THF	57
16	TsOH	4CzIPN	CHCl₃	74
17	TsOH	4CzIPN	EtOH	84

布朗斯特酸/可见光氧化还原接力催化构建喹唑啉(硫)酮