布朗斯特酸/可见光氧化还原接力催化构建喹唑啉(硫)酮

doi:10.6023/cjoc202206001

摘要/Abstract

报道了一种布朗斯特酸/可见光氧化还原接力催化合成喹唑啉(硫)酮的方法. 在温和的反应条件下, 原料2-氨基苯乙酮和异(硫)氰酸酯先后经历了布朗斯特酸催化的[4+2]环化反应和光催化的碳-碳键断裂反应, 得到各种不同取代的喹唑啉-2,4-二酮和喹唑啉-2-硫酮-4-酮. 该合成方法具有能源和溶剂绿色、无金属催化剂、起始原料简单以及以空气作为绿色氧化剂等特点.

关键词: 接力催化, 可见光催化, 绿色合成, 喹唑啉酮

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

引用此文

潘振涛, 刘彤, 马永敏, 颜剑波, 王亚军. 布朗斯特酸/可见光氧化还原接力催化构建喹唑啉(硫)酮[J]. 有机化学, 2022, 42(9): 2823-2831.

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