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Method for synthesizing alpha-ethyl azacycloheptane-2-one substituted pyridine compounds

A technology of heterocycloheptane and compounds, applied in the field of organic synthesis, to achieve the effect of avoiding the use of transition metal catalysts and toxic ligands, less experimental steps, and low technical difficulty

Inactive Publication Date: 2018-04-24
HENAN NORMAL UNIV
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  • Description
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  • Application Information

AI Technical Summary

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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  • Method for synthesizing alpha-ethyl azacycloheptane-2-one substituted pyridine compounds
  • Method for synthesizing alpha-ethyl azacycloheptane-2-one substituted pyridine compounds
  • Method for synthesizing alpha-ethyl azacycloheptane-2-one substituted pyridine compounds

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Experimental program
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Effect test

Embodiment 1-8

[0032] Under a carbon dioxide atmosphere, 0.2 mmol 1,3-butanediyne, 0.2 mmol cesium carbonate, 0.6 mmol DBU, a small amount of water and 2 mL acetonitrile were successively added to a Schlenk reaction tube, and the reaction was heated and stirred at a constant temperature in IKA for 24 h. After the reaction was completed, it was cooled to room temperature, 20 mL of ethyl acetate was transferred to the reaction solution, the sample was prepared by rotary evaporation under reduced pressure, and the target product 3a-3h was obtained by column chromatography separation.

[0033]

[0034]

[0035] In this Example 1-8, a variety of 1,4-diphenylbutadiynes substituted by electron withdrawing and electron donating groups at the para and meta positions of the benzene ring and 1,3-butadiynes substituted by heterocycles and DBU's response. According to the above experiments, it can be found that the reaction has a wide range of substrate adaptability to the alkyl, methoxy, fluoro, c...

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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, in particular to a method for synthesizing α-ethylazepan-2-one substituted pyridine compounds. Background technique [0002] Pyridine, as an important nitrogen-containing heterocycle, exists in a variety of important compounds, including azine, vitamin niacin, and pyridoxine. It is not only a precursor of agrochemicals and drugs, but also an important dye auxiliaries and denaturants. Pyridine derivatives are often part of biomolecules such as pyridine nucleotides and alkaloids. [0003] The synthesis of pyridine is usually divided into two steps: first, the cleavage of the C=N bond of the raw material; second, the reconstruction of the C=N bond to synthesize the pyridine ring. The traditional C=N bond cleavage is to use transition metal M, such as palladium, nickel, copper, cobalt, rhodium and other catalysts to catalyze C=N bond cleavage to form C-M and N-M or C-M-N species. However...

Claims

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Application Information

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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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