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Simple preparation method of 3-aryl indolizine derivative

A technology of indolizine derivatives and aryl groups, which is applied in the field of organic synthetic chemistry to achieve the effects of shortening the process flow, easy availability and low price

Active Publication Date: 2013-06-19
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method also has the following disadvantages: one is that the method is based on indolizine and aryl boronic acid substituted with 3 hydrogens, the former is not commercially available and must be synthesized, and the latter is more expensive; the other is that the method The very expensive palladium catalyst must be used in the preparation process. When the prepared 3-aryl indolizine derivatives are used as intermediates for the production of pharmaceuticals, it may cause the problem that heavy metal palladium in such pharmaceuticals exceeds the standard; the third is When there are omissions or omissions in the operation of the technological process, the heavy metal palladium will be harmful to the environment

Method used

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  • Simple preparation method of 3-aryl indolizine derivative
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  • Simple preparation method of 3-aryl indolizine derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0031] as attached figure 1 According to the technical process, 0.71 g of pyridine (equivalent to 9.0 mmol) and 1.54 g of benzyl bromide (equivalent to 9.0 mmol) were put into the reaction vessel, and 2.0 ml of N,N-dimethylformamide was added. Heat and stir at 40°C for 1.0 hour, add 1.34 g of potassium tert-butoxide (equivalent to 12.0 mmol) and 18 ml of N,N-dimethylformamide into the reaction vessel, and add 0.25 g of methyl propiolate (equivalent to 3.0 mmol) was dissolved in 10 ml of N,N-dimethylformamide, slowly added dropwise to the reaction vessel at 80 degrees, heated and stirred for 4.0 hours to complete the reaction, and the reacted mixture was poured into water, After filtering and washing, 0.38 g of the target product of this example was isolated (51% yield).

[0032] The target product in Example 1 was analyzed by a nuclear magnetic resonance spectrometer (model: AVANCE 400MHz, manufacturer: Bruker, Switzerland) to obtain figure 2 The H NMR spectra shown and ...

Embodiment 2

[0034] as attached figure 1 According to the technological process, 1.16 grams of quinoline (equivalent to 9.0 mmol) and 1.17 grams of p-methylbenzyl chloride (equivalent to 9.0 mmol) were put into the reaction vessel, and 5.0 ml of 1,4-diox Hexacyclic, heated and stirred at 40 degrees for 1.0 hours, added 2.87 g of potassium phosphate (equivalent to 13.5 mmol) and 25 ml of 1,4-dioxane to the reaction vessel, and methyl phenylpropiolate 0.72 g (equivalent to 4.5 mmol) was dissolved in 10 ml of 1,4-dioxane, slowly added dropwise to the reaction vessel at 80 degrees, heated and stirred for 4.0 hours, the reaction was completed, and the reacted mixture was poured into water, filtered, washed, and isolated to obtain 0.78 g of the target product of the example (44% yield).

Embodiment 3

[0036] as attached figure 1 According to the technological process, 1.16 grams of isoquinoline (equivalent to 9.0 mmol) and 2.25 grams of o-bromobenzyl bromide (equivalent to 9.0 mmol) were put into the reaction vessel, and 10 ml of acetonitrile was added, and the Heat and stir under temperature conditions, heat and stir for 1.0 hour, add 5.86 g of cesium carbonate (equivalent to 18 mmol) and 30 ml of acetonitrile into the reaction vessel, dissolve 1.77 g of butynoate methyl ester (equivalent to 18 mmol) in 20 ml Acetonitrile was slowly added dropwise to the reaction vessel at 80 degrees, and the heating and stirring time was 4.0 hours. The reaction was completed, and the reacted mixture was poured into water, filtered, washed, and separated to obtain 2.02 grams of the target product of this embodiment (yield: 57 %).

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Abstract

The invention provides a simple preparation method of a 3-aryl indolizine derivative. The method comprises the following step of: reacting N-benzylpyridine onium salt directly prepared from a pyridine derivative and benzyl halide with electron-deficient alkyne under the existence of alkali to prepare the 3-aryl indolizine derivative. All raw materials used in the simple preparation method can be directly purchased, and are relatively low in price and easy to obtain; any catalyst, ligand and oxidant do not need to be used in the process flow, the process flow is simple, and the cost is obviously reduced; the problem that transition metal in target products exceeds standards is avoided; the whole process is insensitive to air or moisture, and the normal operation can be carried out under loose reaction conditions without polluting the environment; and the simple preparation method can be used for providing the 3-aryl indolizine derivative with abundant sources and low price for the preparation of related products in the fields of biology, pesticides and medicine.

Description

Technical field: [0001] The invention relates to organic synthesis chemistry technology, in particular to a preparation method of indolizine derivatives, in particular to a simple preparation method of 3-aryl indolizine derivatives. Background technique: [0002] Indolizine derivatives are widely used in the fields of biology, pesticides, medicine and luminescent materials, and are necessary for 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-hypert...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 胡华友张宇李国栋阚玉和
Owner 常熟紫金知识产权服务有限公司
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