CN101597293B - Method for preparing purrocoline derivatives by microwave reaction - Google Patents
Method for preparing purrocoline derivatives by microwave reaction Download PDFInfo
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- CN101597293B CN101597293B CN2009101001655A CN200910100165A CN101597293B CN 101597293 B CN101597293 B CN 101597293B CN 2009101001655 A CN2009101001655 A CN 2009101001655A CN 200910100165 A CN200910100165 A CN 200910100165A CN 101597293 B CN101597293 B CN 101597293B
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- microwave reaction
- purrocoline
- derivatives
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Abstract
The present invention discloses a method for preparing purrocoline derivatives by a microwave reaction, belonging to the technical field of chemical synthesis. The method is characterized by comprising the following steps: placing bromoacetophenone, methyl acrylate, pyridine and [CoPy4(HcrO4)2] (TPCD) into a test tube with a ground according to a molar ratio of 1:1-2:1.5-3:1.1-2; sealing the test tube to perform the microwave reaction; separating the mixture to obtain the target product. The method adopts the innovative microwave reaction to prepare the purrocoline derivatives, uses electron-defect olefin which has variable functional group and cheap cost compared with alkyne, and does not need solvent or high temperature, thus being a green and environment-friendly method.
Description
Technical field:
The invention belongs to the synthetic field of organic chemistry, be specifically related to the method that microwave reaction prepares the indolizine derivative.
Background technology:
The indolizine derivative is at biological, agricultural chemicals and pharmaceutically all have been widely used, and they can become medicine, dyestuff and luminescent material.For example: can be used as pigment, weedicide, potential inhibitor of phospholipase enzymes, anti-Leishmania and antiviral etc.; But also showed antimycobacterial activity.They are still synthetic to have the alkaloidal key intermediate of important physiologically active.Discovering subsequently, the biological activity of indolizine derivative is very extensive, mainly contain antitumor, antibiotic, antiviral, kill acarid, anti-inflammatory, anti-arrhythmia, hypertension etc.
All there are some shortcomings in the method for synthetic indolizine derivative in the prior art, and for example: long reaction time, the temperature of reaction height needs a large amount of DMF as solvent, or uses comparatively expensive electron deficiency alkynes, causes the extendability of reacting bad.
Summary of the invention:
The object of the present invention is to provide the preparation method of the indolizine derivative that a kind of production cost is low, reaction conditions is loose and the feature of environmental protection is good.
The technical scheme that the present invention takes for achieving the above object is as follows, and a kind of microwave reaction prepares the method for indolizine derivative, it is characterized in that: with bromoacetophenone, methyl acrylate, pyridine, [CoPy
4(HcrO
4)
2] (TPCD) 1: 1 in molar ratio～2: 1.5～3: 1.1～2 put into and have the ground-in test tube, sealing, microwave reaction separates obtaining target product (formula 1) and hydrolysate (formula 2).
Reaction equation of the present invention is as follows:
As the further setting of the present invention:
Material choice: bromoacetophenone is 1mmol, and methyl acrylate is 1～2mmol, and pyridine is 1.5～3mmol, [CoPy
4(HcrO
4)
2] (TPCD) be 1.1～2mmol; When selecting bromoacetophenone is 0.1990g, and methyl acrylate is 0.1291g, and pyridine is 0.0110g, [CoPy
4(HcrO
4)
2] (TPCD) be 0.1187g, can obtain better effect.
The power of microwave: select 500～1000W, 600 more excellent～800W, 640W are best.
The time of microwave: select 5～15min, best results when 8min or 9min.
Beneficial effect of the present invention is as follows:
The present invention adopts the microwave reaction of innovation, prepares the indolizine derivative, and what the present invention used is the alkene of electron deficiency, compares alkynes, and functional group has more mutability, and low price; The present invention does not need solvent, need not high temperature yet, is the method for an environmental protection.
The invention will be further described below in conjunction with the drawings and specific embodiments.
Description of drawings:
Fig. 1 is the HPLC:Agilent HPLC 1200 of embodiment 1, UV-detector, pillar specifications and models Eclipse XDB-C18,5 μ m, 4.6 * 150mm;
Fig. 2 is the HPLC:Angilent HPLC 1200 of embodiment 2, DAD detector, 20 ℃ of column ovens, pillar specifications and models Eclipse XDB-C18,5 μ m, 4.6 * 150mm;
The condition of HPLC: detect wavelength 365nm flow velocity 0.5mL/min sample size 5 microlitre moving phase (volume ratio) methyl alcohol: water=80: 20.
Embodiment:
Embodiment 1:
With bromoacetophenone 0.1990g, methyl acrylate 0.1291g, pyridine 0.0110g, [CoPy
4(HcrO
4)
2] (TPCD) 0.1187g put into and have the ground-in test tube, sealing, the power of microwave reaction is 640W, reaction times 8min, separating the productive rate obtain target product 1 is 81.5%, the productive rate of hydrolysate 2 is 16.4%, product yield is: 16%, see accompanying drawing 1.
Embodiment 2:
With bromoacetophenone 0.1990g, methyl acrylate 0.1291g, pyridine 0.0110g, [CoPy
4(HcrO
4)
2] (TPCD) 0.1187g put into and have the ground-in test tube, sealing, the power of microwave reaction is 640W, reaction times 9min, separating the productive rate obtain target product 1 is 75.8%, hydrolysate 2 productive rates are 20.6%, product yield is: 18.5%, see accompanying drawing 2.
Embodiment 3:
With unreacted raw material among the embodiment 2, add the 0.0110g pyridine again, be 640W at the power of microwave reaction, reaction times 9min, separating the productive rate that obtains target product 1 is 67.5%, and hydrolysate 2 productive rates are 21.5%, and product yield is: 5.3%.
Embodiment 4:
Preparation method such as embodiment 1, difference is to change microwave reaction power into 800W, and separating the productive rate that obtains target product 1 is 59%, and the productive rate of hydrolysate 2 is 18%, and product yield is: 6.2%,
Embodiment 5:
Preparation method such as embodiment 2, difference is that charging capacity is: bromoacetophenone 0.1990g, methyl acrylate 0.1721g, pyridine 0.0150g, [CoPy
4(HcrO
4)
2] (TPCD) 0.1577g, separating the productive rate that obtains target product 1 is 80.6%, and hydrolysate 2 productive rates are 19.2%, and product yield is: 19.0%.
Claims (2)
1. a microwave reaction prepares the method for indolizine derivative, it is characterized in that: with bromoacetophenone 0.1990g, and methyl acrylate 0.1291g, pyridine 0.0110g, [CoPy
4(HcrO
4)
2] (TPCD) 0.1187g put into and have the ground-in test tube, the sealing, the power of microwave reaction is 640W, reaction times 8min, separate the indolizine derivative.
2. a microwave reaction prepares the method for indolizine derivative, it is characterized in that: with bromoacetophenone 0.1990g, and methyl acrylate 0.1721g, pyridine 0.0150g, [CoPy
4(HcrO
4)
2] (TPCD) 0.1577g, put into and have the ground-in test tube, sealing, the power of microwave reaction is 640W, reaction times 9min, separate the indolizine derivative.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2009101001655A CN101597293B (en) | 2009-07-02 | 2009-07-02 | Method for preparing purrocoline derivatives by microwave reaction |
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|---|---|---|---|
| CN2009101001655A CN101597293B (en) | 2009-07-02 | 2009-07-02 | Method for preparing purrocoline derivatives by microwave reaction |
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|---|---|
| CN101597293A CN101597293A (en) | 2009-12-09 |
| CN101597293B true CN101597293B (en) | 2011-09-14 |
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|---|---|---|---|
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397430B (en) * | 2015-07-28 | 2018-01-12 | 中国科学院化学研究所 | The method for preparing polysubstituted indolinone |
| CN108530442A (en) * | 2018-04-04 | 2018-09-14 | 安徽师范大学 | 1,2,3- tri- replaces Indoli zine derivatives and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1763039A (en) * | 2005-09-15 | 2006-04-26 | 南京师范大学 | Indolizine carboxyl acid analog compound synthesis method |
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2009
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1763039A (en) * | 2005-09-15 | 2006-04-26 | 南京师范大学 | Indolizine carboxyl acid analog compound synthesis method |
Non-Patent Citations (6)
| Title |
|---|
| Bianca Furdui等.Improved Synthesis of Cationic Pyridinium-Substituted Indolizines.《SYNTHESIS》.2006,(第16期),2640-2642. * |
| Rodica M. Dinica等.The Synthesis of Substituted 7,7’-Bis-indolizines via 1,3-Dipolar Cycloaddition under Microwave Irradiation.《SYNLETT》.2000,(第7期),1013-1015. * |
| Utpal Bora等.A Novel Microwave-Mediated One-Pot Synthesis of Indolizines via a Three-Component Reaction.《ORGANIC LETTERS》.2003,第5卷(第4期),435-438. * |
| 乐贵洲等.中氮茚的合成研究进展.《有机化学》.2007,第27卷(第9期),1060-1068. * |
| 李军等.1，3-偶极环加成反应合成中氮茚.《内蒙古大学学报》.1998,第29卷(第3期),373-375. * |
| 沈珠英等.3-吡啶基中氮茚类化合物的合成和荧光性质.《高等学校化学学报》.2008,第29卷916-918. * |
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