Synthesis of 2-Imino-1,2-dihydroquinolines via Copper Catalysis

doi:10.6023/cjoc202102037

Abstract

A mild three-component method for the synthesis of 2-imino-1,2-dihydroquinoline compounds has been successfully developed. In the presence of CuCl, various terminal alkynes, sulfonyl azides and 2-aminobenzaldehydes were coupled. When changing the type of substrate alkyne, controlled synthesis of dihydroquinoline and sulfonyl amidine compounds were achieved.

Key words: 2-imino-1, 2-dihydroquinoline, three-component synthesis, sulfonyl azides, alkynes

Cite this article

Gaige Zhu, Xiaohui Lai, Siyu Wang, Caixia Lin, Yaofeng Yuan. Synthesis of 2-Imino-1,2-dihydroquinolines via Copper Catalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2810-2819.

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Entry^a	Catalyst	Base	Solvent	Yield^b/%
1	CuI	TEA	DCM	73
2	CuBr	TEA	DCM	78
3	CuCl	TEA	DCM	85
4	CuCl₂•2H₂O	TEA	DCM	N.P.^c
5	CuCl	K₂CO₃	DCM	27
6	CuCl	Cs₂CO₃	DCM	23
7	CuCl	Pyridine	DCM	19
8	CuCl	DIEA	DCM	34
9	CuCl	DBU	DCM	trace
10	CuCl	TEA	CH₃CN	73
11	CuCl	TEA	DMF	49
12	CuCl	TEA	THF	33
13	CuCl	TEA	1,4-Dioxane	47
14	CuCl	TEA	DCE	66
15	CuCl	—	DCM	N.P.^c
16	—	TEA	DCM	N.P.^c
17	CuCl	TEA (2 equiv.)	DCM	85
18	CuCl	TEA (0.5 equiv.)	DCM	45
19	CuCl (5 mol%)	TEA	DCM	55
20	CuCl (1 mol%)	TEA	DCM	23

Entry^a	Catalyst	Base	Solvent	Yield^b/%
1	CuI	TEA	DCM	73
2	CuBr	TEA	DCM	78
3	CuCl	TEA	DCM	85
4	CuCl₂•2H₂O	TEA	DCM	N.P.^c
5	CuCl	K₂CO₃	DCM	27
6	CuCl	Cs₂CO₃	DCM	23
7	CuCl	Pyridine	DCM	19
8	CuCl	DIEA	DCM	34
9	CuCl	DBU	DCM	trace
10	CuCl	TEA	CH₃CN	73
11	CuCl	TEA	DMF	49
12	CuCl	TEA	THF	33
13	CuCl	TEA	1,4-Dioxane	47
14	CuCl	TEA	DCE	66
15	CuCl	—	DCM	N.P.^c
16	—	TEA	DCM	N.P.^c
17	CuCl	TEA (2 equiv.)	DCM	85
18	CuCl	TEA (0.5 equiv.)	DCM	45
19	CuCl (5 mol%)	TEA	DCM	55
20	CuCl (1 mol%)	TEA	DCM	23

铜催化合成2-亚氨基-1,2-二氢喹啉化合物