Construction of 3,5-Diarylpyridine Derivatives Using N,N-Dimethyl-ethanolamine as a Single-Carbon Synthon

doi:10.6023/cjoc202405008

Abstract

3,5-Diarylpyridines were effectively synthesized via [2＋2＋1＋1] cyclization reaction catalyzed by Fe(OTf)₃ at 140 ℃, using phenylacetylenes or phenylacetaldehydes, ammonium chloride and N,N-dimethylethanolamine as starting materials. N,N-Dimethylethanolamine was employed as both solvent and a single carbon synthon.

Key words: 3,5-diarylpyridine, N,N-dimethylethanolamine, single carbon synthon, iron catalyzed, cyclization

Cite this article

Xinyu Zhang, Jing Chen, Yongmin Ma. Construction of 3,5-Diarylpyridine Derivatives Using N,N-Dimethyl-ethanolamine as a Single-Carbon Synthon[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3409-3416.

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Entry	Catalyst	Solvent	“N” source (equiv.)	T/℃	Yield/%
1	FeCl₃	DMEA	NH₄OAc (1)	140	21
2	FeCl₃	DMEA	NH₄Cl (1)	140	35
3	FeCl₃	DMEA	NH₄I (1)	140	19
4	FeCl₃	DMEA	(NH₄)₂CO₃ (1)	140	20
5	FeCl₃	DMEA	NH₃^.H₂O (1)	140	Trace
6	FeCl₃	DMEA	Benzylamine (1)	140	0
7	FeCl₃	DMEA	NH₄Cl (2)	140	45
8	FeCl₃	DMEA	NH₄Cl (3)	140	60
9	FeCl₃	DMEA	NH₄Cl (4)	140	55
10	FeCl₂	DMEA	NH₄Cl (3)	140	30
11	Fe(OTf)₃	DMEA	NH₄Cl (3)	140	75
12	Sc(OTf)₃	DMEA	NH₄Cl (3)	140	52
13	Cu(OTf)₂	DMEA	NH₄Cl (3)	140	40
14	Zn(OTf)₂	DMEA	NH₄Cl (3)	140	49
15^b	Fe(OTf)₃	DMSO	NH₄Cl (3)	140	30
16^b	Fe(OTf)₃	DMF	NH₄Cl (3)	140	43
17^b	Fe(OTf)₃	Xylenes	NH₄Cl (3)	140	25
18^b	Fe(OTf)₃	CH₃CN	NH₄Cl (3)	140	20
19^c	Fe(OTf)₃	DMSO/DMF	NH₄Cl (3)	140	0
20	Fe(OTf)₃	DMEA	NH₄Cl (3)	80	0
21	Fe(OTf)₃	DMEA	NH₄Cl (3)	100	12
22	Fe(OTf)₃	DMEA	NH₄Cl (3)	120	36
23	Fe(OTf)₃	DMEA	NH₄Cl (3)	160	40

Entry	Catalyst	Solvent	“N” source (equiv.)	T/℃	Yield/%
1	FeCl₃	DMEA	NH₄OAc (1)	140	21
2	FeCl₃	DMEA	NH₄Cl (1)	140	35
3	FeCl₃	DMEA	NH₄I (1)	140	19
4	FeCl₃	DMEA	(NH₄)₂CO₃ (1)	140	20
5	FeCl₃	DMEA	NH₃^.H₂O (1)	140	Trace
6	FeCl₃	DMEA	Benzylamine (1)	140	0
7	FeCl₃	DMEA	NH₄Cl (2)	140	45
8	FeCl₃	DMEA	NH₄Cl (3)	140	60
9	FeCl₃	DMEA	NH₄Cl (4)	140	55
10	FeCl₂	DMEA	NH₄Cl (3)	140	30
11	Fe(OTf)₃	DMEA	NH₄Cl (3)	140	75
12	Sc(OTf)₃	DMEA	NH₄Cl (3)	140	52
13	Cu(OTf)₂	DMEA	NH₄Cl (3)	140	40
14	Zn(OTf)₂	DMEA	NH₄Cl (3)	140	49
15^b	Fe(OTf)₃	DMSO	NH₄Cl (3)	140	30
16^b	Fe(OTf)₃	DMF	NH₄Cl (3)	140	43
17^b	Fe(OTf)₃	Xylenes	NH₄Cl (3)	140	25
18^b	Fe(OTf)₃	CH₃CN	NH₄Cl (3)	140	20
19^c	Fe(OTf)₃	DMSO/DMF	NH₄Cl (3)	140	0
20	Fe(OTf)₃	DMEA	NH₄Cl (3)	80	0
21	Fe(OTf)₃	DMEA	NH₄Cl (3)	100	12
22	Fe(OTf)₃	DMEA	NH₄Cl (3)	120	36
23	Fe(OTf)₃	DMEA	NH₄Cl (3)	160	40

以N,N-二甲基乙醇胺为单碳合成子构建3,5-二芳基吡啶的新方法