Copper-catalyzed Synthesis of Amides from Alcohols and Aminopyridines Under Aerobic Conditions

doi:10.7503/cjcu20230029

Abstract

Abstract:

N-（pyridine-2-yl）amides were synthesized in one step with benzyl alcohols and 2-aminopyridines in copper-catalyzed aerobic conditions by air bubbling method. The mechanism study demonstrated that benzaldehydes were formed in situ from benzyl alcohols under aerobic conditions and acted as coupling partners to react with 2-aminopyridines to synthesize amides. The bioactivity study showed that the synthesized products possessed certain antibacterial activity. This reaction features high efficiency and functional group tolerance. Moreover， no additives were used in the reaction and this method utilized oxygen from the air as an ideal oxidant with the virtue of economy and green.

Key words: Copper-catalyzed synthesis, Aerobic, Alcohol, Amide

CLC Number:

O621

TrendMD:

YANG Wei, LIU Jiaqi, TANG Cuiman, ZHANG Haonan, WANG Bingbing, SUN Zhong, XU Xiaohui. Copper-catalyzed Synthesis of Amides from Alcohols and Aminopyridines Under Aerobic Conditions[J]. Chem. J. Chinese Universities, 2023, 44(8): 20230029.

Figures/Tables 3

References 34

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Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
3a	81—82	3f	70—71	3m	120—121	3s	94—95
3b	103—104	3g	136—137	3n	107—108	3t	99—100
3c	102—103	3h	81—82	3o	105—106	3u	120—121
3d	137—138	3k	148—149	3p	118—119	3x	107—108
3e	111—112	3l	70—71	3r	129—130

Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
3a	81—82	3f	70—71	3m	120—121	3s	94—95
3b	103—104	3g	136—137	3n	107—108	3t	99—100
3c	102—103	3h	81—82	3o	105—106	3u	120—121
3d	137—138	3k	148—149	3p	118—119	3x	107—108
3e	111—112	3l	70—71	3r	129—130

Entry	Catalyst	Solvent	Temperature/℃	Time/h	Yield ^b （%）
1	CuI	DMF	70	12	31
2	CuI	DMF	90	12	40
3	CuI	DMF	110	16	62
4	CuI	MeOH	110	16	13
5	CuI	CH₃CN	110	16	50
6	CuI	DMA	110	12	39
7	CuI	NMP	110	16	45
8	CuI	THF	110	16	Trace
9	CuI	HFIP	110	14	31
10	CuCl	DMF	110	12	Trace
11	CuBr	DMF	110	12	Trace
12 ^c	CuI	DMF	110	16	92

Entry	Catalyst	Solvent	Temperature/℃	Time/h	Yield ^b （%）
1	CuI	DMF	70	12	31
2	CuI	DMF	90	12	40
3	CuI	DMF	110	16	62
4	CuI	MeOH	110	16	13
5	CuI	CH₃CN	110	16	50
6	CuI	DMA	110	12	39
7	CuI	NMP	110	16	45
8	CuI	THF	110	16	Trace
9	CuI	HFIP	110	14	31
10	CuCl	DMF	110	12	Trace
11	CuBr	DMF	110	12	Trace
12 ^c	CuI	DMF	110	16	92

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