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The preparation method of 1,3-disubstituted indolizine derivatives

A technology of indolizine derivatives and di-substitution, which is applied in the field of preparation of indolizine derivatives, can solve the problems of increased synthesis cost and environmental protection cost, environmental hazards of transition metal salts, long production cycle, etc., and achieves no environmental pollution Risk, resource abundance, and efficiency-enhancing effects

Active Publication Date: 2018-02-23
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing technology has the following disadvantages: first, it needs to use equivalent toxic and harmful oxidants, which increases the synthesis cost and environmental protection cost; second, the multi-step synthesis method must be used in the existing process, resulting in long production cycle and low efficiency; Third, if there are omissions in the process operation, a large amount of transition metal salts will cause harm to the environment

Method used

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  • The preparation method of 1,3-disubstituted indolizine derivatives
  • The preparation method of 1,3-disubstituted indolizine derivatives
  • The preparation method of 1,3-disubstituted indolizine derivatives

Examples

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Effect test

Embodiment 1

[0030] as attached figure 1 According to the technical process, 18.6 mg of aniline (equivalent to 0.20 mmol), 29.4 mg of maleic anhydride (equivalent to 0.30 mmol) and 0.20 ml of ethyl acetate were added to the container, and under stirring, the reaction was heated at 60 degrees Celsius for 3 hours. A sample spot plate showed complete reaction of the aniline. Continue to add 51.7 mg of isoquinoline (equivalent to 0.40 mmol) and 66.8 mg of ethyl α-bromoacetate (equivalent to 0.40 mmol) to the mixture obtained above, continue to heat the reaction at 60 degrees Celsius for 4 hours, take a sample point plate, and show The raw material reacted completely. 8.6 mg of cuprous bromide (corresponding to 0.06 mmol), 55.2 mg of potassium carbonate (corresponding to 0.40 mmol) and 1.8 ml of dimethyl sulfoxide were further added to the mixture obtained above, and oxygen was introduced. The mixture was heated and stirred at 100° C. for 12 hours under 1 atmospheric pressure of oxygen, and a...

Embodiment 2

[0034] as attached figure 1 The technological process of getting 4-methoxyaniline is 24.6 mg (equivalent to 0.20 mmol), 19.6 mg of maleic anhydride (equivalent to 0.20 mmol) and 0.10 ml of ethyl acetate, heated at 50 degrees Celsius for 7 hours, and sampling Spot the plate, showing that the raw material has reacted completely. Continue to add 27.9 mg of 4-picoline (equivalent to 0.30 mmol) and 36.8 mg of ethyl α-chloroacetate (equivalent to 0.30 mmol) to the mixture obtained above, continue to heat at 80 degrees Celsius for 4 hours, and take a sample point plate, It shows that the reaction of raw materials is complete. Continue to add 5.4 mg of copper acetate (equivalent to 0.03 mmol), 45.0 mg of potassium bicarbonate (equivalent to 0.45 mmol) and N , N- Dimethylformamide 2.4 ml, bubbled with oxygen. The mixture was heated and stirred at 80° C. for 16 hours under 1 atmospheric pressure of oxygen, and a plate was taken to show that the reaction of the raw materials was comp...

Embodiment 3

[0036] as attached figure 1 The technological process of getting p-chloroaniline is 25.5 mg (equivalent to 0.20 mmol), maleic anhydride 29.4 mg (equivalent to 0.30 mmol) and 0.25 milliliters of ethyl acetate, heated at 60 degrees Celsius for 5 hours, sampling point plate, It shows that the reaction of raw materials is complete. Continue to add 77.6 mg of 4-phenylpyridine (equivalent to 0.50 mmol) and 139.0 mg of α,4-dibromoacetophenone (equivalent to 0.50 mmol) to the mixture obtained above, continue heating at 70 degrees Celsius for 5 hours, and take a sample Spot the plate, showing that the raw material has reacted completely. Continue to add 4.5 mg of copper bromide (equivalent to 0.02 mmol) in the mixture obtained above, 162.9 mg of cesium carbonate (equivalent to 0.50 mmol) and N , N - Dimethylacetamide 2.0 ml, bubbled with oxygen. The mixture was heated and stirred at 100° C. for 8 hours under 1 atmospheric pressure of oxygen, and a sample was taken, which showed tha...

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Abstract

The invention discloses a method for preparing a 1,3-disubstituted indolizine derivative. The method comprises the following steps: by taking amine, maleic anhydride, pyridine and an alpha-halogenated compound as raw materials, copper salt as a catalyst and oxygen as an oxidant, preparing the 1,3-disubstituted indolizine derivative in the presence of alkali. According to the method, a process of a one-pot method is adopted, reaction is implemented in one same reactor, no any intermediate needs to be purified, and the synthesis efficiency is greatly improved; only a catalytic amount of a copper catalyst and the environment-friendly oxidant oxygen are used in the process, so that a post treatment process is relatively simple, and the environment pollution risk can be avoided; the whole process is not sensitive to air and humidity, and normal operation can be implanted under a loose reaction condition; and related products can be prepared for fields such as biologics, pesticides and medicines, and the 1,3-disubstituted indolizine derivative which is rich in resource and relatively low in price can be provided.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of indolizine derivatives, in particular to a preparation method of 1,3-disubstituted indolizine derivatives. Background technique [0002] Indolizine derivatives are widely used in the fields of biology, pesticides, medicine and luminescent materials, and are intermediates in the production of drugs, dyes and organic luminescent materials. For example: it is an active ingredient in pigments, herbicides, latent phospholipase inhibitors, anti-Leishmania and antiviral drugs; in addition, it also exhibits anti-mycobacterial activity; it is a synthetic compound with important physiological activities Key intermediates of alkaloids. In recent years, studies have confirmed that the biological activity of indolizine derivatives has also played a positive role in anti-tumor, anti-bacterial, anti-virus, acaricidal, anti-inflammatory, anti-arrhythmic, anti-hypertensiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 胡华友徐娟芳支三军王翔阚玉和张宇
Owner HUAIYIN TEACHERS COLLEGE
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