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A method for synthesizing α-ethylazepan-2-one substituted pyridine compounds

A technology of heterocycloheptane and compound, applied in the field of organic synthesis, to avoid the use of transition metal catalysts and toxic ligands, to promote cleavage, and to achieve the effects of few experimental steps

Inactive Publication Date: 2020-08-28
HENAN NORMAL UNIV
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Problems solved by technology

At present, carbon dioxide fixation chemistry has been vigorously developed, but there is no public report on the activation of C=N to promote the breakage of C=N bonds and then the reconstruction of C=N bonds to form pyridine heterocycles.

Method used

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  • A method for synthesizing α-ethylazepan-2-one substituted pyridine compounds
  • A method for synthesizing α-ethylazepan-2-one substituted pyridine compounds
  • A method for synthesizing α-ethylazepan-2-one substituted pyridine compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1-8

[0033] Under a carbon dioxide atmosphere, 0.2 mmol of 1,3-butadiyne, 0.2 mmol of cesium carbonate, 0.6 mmol of DBU, a small amount of water and 2 mL of acetonitrile were sequentially added into the Schlenk reaction tube, and the reaction was heated and stirred in IKA for 24 hours. After the reaction, cooled to room temperature, 20 mL of ethyl acetate was used to transfer the reaction liquid, and the sample was prepared by rotary evaporation under reduced pressure, and the target product 3a-3h was obtained by column chromatography separation.

[0034]

[0035]

[0036] In this example 1-8, a variety of 1,4-diphenylbutadiynes substituted by electron-withdrawing and electron-donating groups at the para-position and meta-position of the benzene ring and 1,3-butadiyne and heterocyclic substituted 1,3-butadiynes were studied. DBU's response. According to the above experiments, it can be found that the reaction has a wide range of substrate adaptability to the substituents such...

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Abstract

The invention discloses a method for synthesizing alpha-ethyl azacycloheptane-2-one substituted pyridine compounds and belongs to the technical field of organic chemistry. According to the method, DBUand 1,3-butadiyne compounds are taken as reaction raw materials and subjected to heating reaction in alkaline cesium salt and an acetonitrile solution under promoting action of CO2, and the polysubstituted pyridine compounds are obtained. C=N bond rupture is promoted through CO2 activation, the method is simple and convenient, conditions are mild, the functional polysubstituted pyridine compoundsare directly constructed, and the synthesis method of pyridine heterocyclic rings is broadened.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing pyridine compounds substituted by α-ethylazepan-2-one. Background technique [0002] As an important nitrogen-containing heterocycle, pyridine exists in a variety of important compounds, including azine, vitamin niacin, and pyridoxine. It is not only the precursor of agricultural chemicals and drugs, but also an important dyeing aid and denaturant. Pyridine derivatives are often part of biomolecules, such as pyridine nucleotides and alkaloids. [0003] The synthesis of pyridine is usually divided into two steps: 1. breaking of the C=N bond of the raw material; 2. rebuilding of the C=N bond to synthesize the pyridine ring. Traditional C=N bond breaking is to use transition metal M, such as palladium, nickel, copper, cobalt, rhodium and other catalysts to catalyze the breaking of C=N bonds to form C-M and N-M or C-M-N substances. H...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06C07D409/14
CPCC07D401/06C07D409/14
Inventor 刘建明岳园园闫旭洋赵淑芳王科邵慧彬
Owner HENAN NORMAL UNIV
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