Quinolizinone compound and preparation method thereof

A compound, quinozinone technology, applied in the field of organic chemical synthesis, can solve the problems of high equipment cost, harsh reaction conditions, long production cycle, etc., and achieve the effect of high yield, short reaction time and less reaction equipment

Inactive Publication Date: 2021-01-05
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods have higher yields, these reactions often require the preactivation of the substrate, and need to go through multi-step reactions, harsh reaction conditions, and long production cycles, which cause high equipment costs. Therefore, in practice are greatly limited in application

Method used

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  • Quinolizinone compound and preparation method thereof
  • Quinolizinone compound and preparation method thereof
  • Quinolizinone compound and preparation method thereof

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preparation example Construction

[0027] The preparation method of the quinazinone compound that the present invention proposes, concrete process is as follows:

[0028] Using alkynyl ester propiolate compounds as raw materials, adding pyridine derivatives to the raw material, the added molar ratio is: alkynyl ester propiolates: pyridine derivatives=(2.5~3):1 to obtain a mixture , add ethyl acetate in the mixture, the mass ratio of adding is: mixture: ethyl acetate=1: (10~18), add alkali again, the add-on of alkali is identical with alkynes propiolates, at 60 ℃~80℃, react for 3~5 hours, cool to room temperature, distill under reduced pressure to remove the solvent in the reaction product, wash with water several times, remove the inorganic salt in the reaction product, adopt column chromatography to collect quinazone class of compounds.

[0029] In the preparation method of the above-mentioned quinazinone compounds, the base is any one of cesium carbonate, cesium hydroxide, potassium hydroxide, potassium carb...

Embodiment 1

[0032] The molecular structural formula of the prepared quinazinone is as follows:

[0033]

[0034] The specific process is: taking ethyl propiolate (294mg, 3mmol) as raw material, adding 2-pyridineacetonitrile (118mg, 1mmol) to the raw material, the molar ratio added is: ethyl propiolate:2-pyridineacetonitrile=3 : 1, obtain mixture, add solvent in mixture, the mass ratio of adding is: mixture: solvent=1:15, described solvent is ethyl acetate, adds alkali again, and the add-on of alkali is identical with ethyl propiolate , the base is cesium carbonate (977.4mg, 3mmol), reacted at 80 degrees for 3 hours, cooled to room temperature, evaporated under reduced pressure to remove the solvent in the reaction product, washed with water several times, and removed the inorganic salt in the reaction product , using column chromatography to collect quinozinone compounds, the yield was 215 mg, and the yield was 80%. During the column chromatography, the eluent added was a mixed soluti...

Embodiment 2

[0036] The molecular structural formula of the prepared quinazinone is as follows:

[0037]

[0038] The specific process is: taking ethyl propiolate (294mg, 3mmol) as raw material, adding 2-pyridineacetonitrile (118mg, 1mmol) to the raw material, the molar ratio added is: ethyl propiolate:2-pyridineacetonitrile=3 : 1, obtain mixture, add solvent in mixture, the mass ratio of adding is: mixture: solvent=1:15, described solvent is ethyl acetate, adds alkali again, and the add-on of alkali is identical with ethyl propiolate , the base is cesium hydroxide (450mg, 3mmol), reacted at 80 degrees for 3 hours, cooled to room temperature, distilled under reduced pressure to remove the solvent in the reaction product, washed with water several times, and removed the inorganic salt in the reaction product , using column chromatography to collect quinozinone compounds, the yield was 187 mg, and the yield was 70%. During the column chromatography, the eluent added was a mixed solution ...

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Abstract

The invention relates to a quinolizinone compound and a preparation method thereof, and belongs to the technical field of organic chemical synthesis. The molecular structural formula of the quinolizidone compound is shown in the specification. The preparation method comprises the following steps: by taking an alkyne ester propiolate compound as a raw material, adding a pyridine derivative into theraw material, adding ethyl acetate into the mixture, then adding alkali, reacting at a proper temperature, cooling to room temperature, carrying out reduced pressure distillation to remove a solventin a reaction product, washing with water for multiple times, removing the inorganic salt in a reaction product, and collecting to obtain the quinolizinone compound by adopting a column chromatographymethod. According to the method, the raw materials required by the reaction are easy to obtain, the yield is high, the reaction conditions are mild, the reaction time is short, and the reaction stepsare few, so that the used reaction equipment is few, and the post-treatment is simple and convenient.

Description

technical field [0001] The invention relates to a quinozinone compound and a preparation method thereof. Specifically, a series of quinazinone compounds substituted at the 3-position are synthesized by using propiolate and 2-pyridine acetonitrile as raw materials, belonging to organic chemical synthesis technology field. [0002] technical background [0003] Quinazinones are a class of nitrogen-hybridized compounds with special physical and chemical properties and important medical potential applications. They can be used for the treatment of Alzheimer's disease, type II diabetes, and immunoglobulin E-related diseases. [0004] The synthetic method of quinazinone compound mainly contains three kinds at present, (1) condensation reaction of ethyl 2-pyridine acetate and diethyl ethoxymethylene malonate; (2) picoline substituted by α and β, β-dichloro Cyclization of acrolein; (3) Horner-Wadsworth-Emmons olefination / cyclization of β-carbonylpyridine and phosphate. Although the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/02C07D455/06
CPCC07D455/02C07D455/06
Inventor 龚汉元房继旺
Owner BEIJING NORMAL UNIVERSITY
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