Copper-Catalyzed Cyclization Reaction of 3-Nitrochromenes with Enaminones to Synthesize of 2H-Chromeno-pyrrole Derivatives

doi:10.6023/cjoc202507037

Abstract

Chromeno-pyrrole derivatives exhibit a wide range of biological and pharmacological activities. Herein, a novel approach to the synthesis of molecular diversity 2H-chromeno-pyrrole has been developed from [3＋2] cyclization of 3-nitrochromenes. The reaction is catalyzed by CuI with 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine (DBN) as the promoter at room temperature. This reaction has the advantages of good functional group compatibility, broad substrate universality, and mild reaction conditions.

Key words: copper catalysis, [3＋2] cyclization, 2H-chromeno-pyrroles, 3-nitrochromenes, enaminones

Cite this article

Wanting Liang, Siyi Chen, Enqi Xu, Xuebing Chen. Copper-Catalyzed Cyclization Reaction of 3-Nitrochromenes with Enaminones to Synthesize of 2H-Chromeno-pyrrole Derivatives[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 496-506.

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Entry	Solvent	Promoter	Metal	T/℃	Yield^b/%
1	EtOH	—	—	r.t.~reflux	N.R.
2	EtOH	DBU	CuCl₂	r.t.	25
3	EtOH	DBU	CuBr	r.t.	30
4	EtOH	DBU	CuI	r.t.	30
5	EtOH	DBU	AgNO₃	r.t.	28
6	EtOH	DBU	Fe₂O₃	r.t.	10
7	EtOH	DBU	FeCl₃	r.t.	7
8	EtOH	DBU	InCl₃	r.t.	26
9	CH₃OH	DBU	CuI	r.t.	25
10	Toluene	DBU	CuI	r.t.	45
11	DMSO	DBU	CuI	r.t.	40
12	CH₃CN	DBU	CuI	r.t.	45
13	DMF	DBU	CuI	r.t.	15
14	1,4-Dioxane	DBU	CuI	r.t.	N.R.
15	THF	DBU	CuI	r.t.	40
16	CH₃CN	DBN	CuI	r.t	51
17	CH₃CN	Cs₂CO₃	CuI	r.t	38
18	CH₃CN	K₂CO₃	CuI	r.t	35
19	CH₃CN	Piperidine	CuI	r.t	10
20	CH₃CN	TEA	CuI	r.t	20
21	CH₃CN	DABCO	CuI	r.t	10
22	CH₃CN	CF₃COOH	CuI	r.t	N.R.
23	CH₃CN	TsOH	CuI	r.t	N.R.
24^c	CH₃CN	DBN	CuI	r.t.	44
25^d	CH₃CN	DBN	CuI	r.t.	50
26	CH₃CN	DBN	CuI	60	45
27	CH₃CN	—	CuI	r.t	N.R.
28	CH₃CN	DBN	—	r.t	5

Entry	Solvent	Promoter	Metal	T/℃	Yield^b/%
1	EtOH	—	—	r.t.~reflux	N.R.
2	EtOH	DBU	CuCl₂	r.t.	25
3	EtOH	DBU	CuBr	r.t.	30
4	EtOH	DBU	CuI	r.t.	30
5	EtOH	DBU	AgNO₃	r.t.	28
6	EtOH	DBU	Fe₂O₃	r.t.	10
7	EtOH	DBU	FeCl₃	r.t.	7
8	EtOH	DBU	InCl₃	r.t.	26
9	CH₃OH	DBU	CuI	r.t.	25
10	Toluene	DBU	CuI	r.t.	45
11	DMSO	DBU	CuI	r.t.	40
12	CH₃CN	DBU	CuI	r.t.	45
13	DMF	DBU	CuI	r.t.	15
14	1,4-Dioxane	DBU	CuI	r.t.	N.R.
15	THF	DBU	CuI	r.t.	40
16	CH₃CN	DBN	CuI	r.t	51
17	CH₃CN	Cs₂CO₃	CuI	r.t	38
18	CH₃CN	K₂CO₃	CuI	r.t	35
19	CH₃CN	Piperidine	CuI	r.t	10
20	CH₃CN	TEA	CuI	r.t	20
21	CH₃CN	DABCO	CuI	r.t	10
22	CH₃CN	CF₃COOH	CuI	r.t	N.R.
23	CH₃CN	TsOH	CuI	r.t	N.R.
24^c	CH₃CN	DBN	CuI	r.t.	44
25^d	CH₃CN	DBN	CuI	r.t.	50
26	CH₃CN	DBN	CuI	60	45
27	CH₃CN	—	CuI	r.t	N.R.
28	CH₃CN	DBN	—	r.t	5

铜催化3-硝基色烯与烯胺酮环化反应合成2H-色烯并吡咯衍生物