苯并磺内酰胺联吡唑化合物的简便合成

doi:10.6023/cjoc202209009

摘要/Abstract

报道了一种碱调节的快速合成苯并磺内酰胺联吡唑化合物的方法. 在三乙胺和乙酸酐存在下, 苯并磺内酰亚胺与吡唑-5-酮能够顺利地进行Mannich反应, 并以高收率得到加成产物. 推测了可能的反应机理, 反应放大到克级规模, 同样能够以高收率获得产物.

关键词: 吡唑, 苯并磺内酰胺, 曼尼希加成, 吡唑啉酮

A base-mediated rapid synthesis of benzosultam-linked pyrazole compounds was developed. The reaction of N-sulfonyl ketimine with pyrazolin-5-one proceeded smoothly to provide the desired products in high yields in the presence of Et₃N and Ac₂O. The possible mechanism was proposed. This reaction could be conducted on a gram-scale with maintained high yield.

Key words: pyrazole, benzosultam, Mannich addition, pyrazolone

引用此文

雷容超, 兰文捷, 李梦竹, 傅滨. 苯并磺内酰胺联吡唑化合物的简便合成[J]. 有机化学, 2023, 43(7): 2553-2560.

Rongchao Lei, Wenjie Lan, Mengzhu Li, Bin Fu. A Convenient Approach to Benzosultam-Linked Pyrazole Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2553-2560.

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Entry	Solvent	Base	T/℃	Yield/%
1	CHCl₃	Et₃N	r.t.	52
2	CH₂Cl₂	Et₃N	r.t.	48
3	Et₂O	Et₃N	r.t.	65
4	CH₃CO₂Et	Et₃N	r.t.	41
5	Toluene	Et₃N	r.t.	44
6	THF	Et₃N	r.t.	98
7	THF	Na₂CO₃	r.t.	60
8	THF	K₂CO₃	r.t.	40
9	THF	Cs₂CO₃	r.t.	41
10	THF	NaOH	r.t.	30
11	THF	MeONa	r.t.	30
12	THF	Pyridine	r.t.	62
13	THF	DIEPA	r.t.	75
14	THF	Et₃N	0	93
15	THF	Et₃N	35	83

Entry	Solvent	Base	T/℃	Yield/%
1	CHCl₃	Et₃N	r.t.	52
2	CH₂Cl₂	Et₃N	r.t.	48
3	Et₂O	Et₃N	r.t.	65
4	CH₃CO₂Et	Et₃N	r.t.	41
5	Toluene	Et₃N	r.t.	44
6	THF	Et₃N	r.t.	98
7	THF	Na₂CO₃	r.t.	60
8	THF	K₂CO₃	r.t.	40
9	THF	Cs₂CO₃	r.t.	41
10	THF	NaOH	r.t.	30
11	THF	MeONa	r.t.	30
12	THF	Pyridine	r.t.	62
13	THF	DIEPA	r.t.	75
14	THF	Et₃N	0	93
15	THF	Et₃N	35	83

Entry	R²	R³	Product	Yield/%
1	2-MeC₆H₄	Ph	3ab	94
2	2-CF₃C₆H₄	Ph	3ac	85
3	3-MeC₆H₄	Ph	3ad	82
4	3-FC₆H₄	Ph	3ae	98
5	4-MeOC₆H₄	Ph	3af	96
6	4-BrC₆H₄	Ph	3ag	91
7	Naphthyl	Ph	3ah	87
8	Ph	4-MeC₆H₄	3ai	98
9	Ph	4-ClC₆H₄	3aj	87
10	Ph	3-MeOC₆H₄	3ak	82
11	Ph	3-BrC₆H₄	3al	82
12	Ph	2-FC₆H₄	3am	92
13	Ph	Cyclohexyl	3an	90
14	Ph	H	3ao	—

Entry	R²	R³	Product	Yield/%
1	2-MeC₆H₄	Ph	3ab	94
2	2-CF₃C₆H₄	Ph	3ac	85
3	3-MeC₆H₄	Ph	3ad	82
4	3-FC₆H₄	Ph	3ae	98
5	4-MeOC₆H₄	Ph	3af	96
6	4-BrC₆H₄	Ph	3ag	91
7	Naphthyl	Ph	3ah	87
8	Ph	4-MeC₆H₄	3ai	98
9	Ph	4-ClC₆H₄	3aj	87
10	Ph	3-MeOC₆H₄	3ak	82
11	Ph	3-BrC₆H₄	3al	82
12	Ph	2-FC₆H₄	3am	92
13	Ph	Cyclohexyl	3an	90
14	Ph	H	3ao	—