钌催化喹唑啉酮与碳酸亚乙烯酯的C—H [4＋2]环化反应

doi:10.6023/cjoc202210003

摘要/Abstract

过渡金属催化下的惰性C—H环化反应作为有机化学领域的一种高效策略, 可构筑一系列碳环及杂环分子骨架. 近年来, 化学家们利用碳酸亚乙烯酯作为碳合成子, 并借助其特殊的结构、无氧化剂的催化体系以及碳酸为唯一副产物的优势, 为构建非取代杂环化合物提供了一种新思路. 提出一类在钌催化下, 喹唑啉酮与碳酸亚乙烯酯发生的C—H [4＋2]环化反应, 并以良好的收率获得2,3-稠合喹唑啉酮衍生物.

关键词: 钌催化, C—H环化反应, 酸亚乙烯酯, 稠合喹唑啉酮

Transition metal-catalyzed inert C—H annulation reaction, an efficient strategy in the field of organic chemistry, is capable of constructing a series of carbon- or heterocycle molecules. Very recently, organic chemists have commenced to employ vinylene carbonate as a carbon synthon for the efficient construction of non-substituted heterocyclic compounds, which benefits with the enriched product structure, quite simple and concise reaction system, and the sole carbonic acid as by-product. A new type of C—H [4＋2] cyclization reaction of quinazolinone with ethylene carbonate catalyzed by ruthenium is proposed, and 2,3-fused quinazolinone derivatives are obtained with good yields.

Key words: ruthenium catalysis, C—H cyclization reaction, vinylene carbonate, fused quinazolone

引用此文

南江, 黄冠杰, 胡岩, 王波. 钌催化喹唑啉酮与碳酸亚乙烯酯的C—H [4＋2]环化反应[J]. 有机化学, 2023, 43(4): 1537-1549.

Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4＋2] Annulation of Quinazolinones with Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.

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参考文献 15

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Entry	Catalyst	Additive	Temp./℃	Solvent	Yield^b/% of 3a	Yield^c/% of 4a
1	Cp*Rh(MeCN)₃(SbF₆)₂		100	1,4-Dioxane	32	T race
2	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	1,4-Dioxane	35	Trace
3	[Cp*Co(CO)I₂]₂	AgSbF₆	100	1,4-Dioxane	17	Trace
4	[Cp*IrCl₂]₂	AgSbF₆	100	1,4-Dioxane	24	Trace
5	[Ru(p-cymene)Cl₂]₂		100	1,4-Dioxane	12	Trace
6		AgSbF₆	100	1,4-Dioxane	Trace	Trace
7	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	ⁱPrOH	Trace	Trace
8	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	Toluene	Trace	Trace
9	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	DMF	21	Trace
10	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	DCE	42	Trace
11	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	MeCN	26	Trace
12	[Ru(p-cymene)Cl₂]₂	AgOTf	100	DCE	28	Trace
13	[Ru(p-cymene)Cl₂]₂	AgNTf₂	100	DCE	25	Trace
14	[Ru(p-cymene)Cl₂]₂	AgOAc	100	DCE	Trace	Trace
15	[Ru(p-cymene)Cl₂]₂	AgSbF₆	50	DCE	Trace	58
16	[Ru(p-cymene)Cl₂]₂	AgSbF₆	60	DCE	Trace	82
17	[Ru(p-cymene)Cl₂]₂	AgSbF₆	70	DCE	Trace	71
18	[Ru(p-cymene)Cl₂]₂	AgSbF₆	80	DCE	15	14
19	[Ru(p-cymene)Cl₂]₂	AgSbF₆	120	DCE	53	Trace
20	[Ru(p-cymene)Cl₂]₂	AgSbF₆	140	DCE	61	Trace
21^d	[Ru(p-cymene)Cl₂]₂	AgSbF₆	140	DCE	75	Trace

Entry	Catalyst	Additive	Temp./℃	Solvent	Yield^b/% of 3a	Yield^c/% of 4a
1	Cp*Rh(MeCN)₃(SbF₆)₂		100	1,4-Dioxane	32	T race
2	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	1,4-Dioxane	35	Trace
3	[Cp*Co(CO)I₂]₂	AgSbF₆	100	1,4-Dioxane	17	Trace
4	[Cp*IrCl₂]₂	AgSbF₆	100	1,4-Dioxane	24	Trace
5	[Ru(p-cymene)Cl₂]₂		100	1,4-Dioxane	12	Trace
6		AgSbF₆	100	1,4-Dioxane	Trace	Trace
7	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	ⁱPrOH	Trace	Trace
8	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	Toluene	Trace	Trace
9	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	DMF	21	Trace
10	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	DCE	42	Trace
11	[Ru(p-cymene)Cl₂]₂	AgSbF₆	100	MeCN	26	Trace
12	[Ru(p-cymene)Cl₂]₂	AgOTf	100	DCE	28	Trace
13	[Ru(p-cymene)Cl₂]₂	AgNTf₂	100	DCE	25	Trace
14	[Ru(p-cymene)Cl₂]₂	AgOAc	100	DCE	Trace	Trace
15	[Ru(p-cymene)Cl₂]₂	AgSbF₆	50	DCE	Trace	58
16	[Ru(p-cymene)Cl₂]₂	AgSbF₆	60	DCE	Trace	82
17	[Ru(p-cymene)Cl₂]₂	AgSbF₆	70	DCE	Trace	71
18	[Ru(p-cymene)Cl₂]₂	AgSbF₆	80	DCE	15	14
19	[Ru(p-cymene)Cl₂]₂	AgSbF₆	120	DCE	53	Trace
20	[Ru(p-cymene)Cl₂]₂	AgSbF₆	140	DCE	61	Trace
21^d	[Ru(p-cymene)Cl₂]₂	AgSbF₆	140	DCE	75	Trace