CN104311521A - Method for synthesizing bishydroxycoumarin compound by choline ionic liquid catalysis - Google Patents
Method for synthesizing bishydroxycoumarin compound by choline ionic liquid catalysis Download PDFInfo
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- CN104311521A CN104311521A CN201410480624.8A CN201410480624A CN104311521A CN 104311521 A CN104311521 A CN 104311521A CN 201410480624 A CN201410480624 A CN 201410480624A CN 104311521 A CN104311521 A CN 104311521A
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- ionic liquid
- choline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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Abstract
The invention discloses a method for synthesizing a bishydroxycoumarin compound by choline ionic liquid catalysis. The key points of the technical scheme provided by the invention are as below: the method for synthesizing the bishydroxycoumarin compound by choline ionic liquid catalysis uses aromatic aldehydes and 4-hydroxy coumarin as raw materials, and an aqueous solution of choline ionic liquid as a catalyst system and solvent; and the raw materials, catalyst system and solvent are heated to 25-70 DEG C under normal pressure for synthesis of the bishydroxycoumarin compound. The choline ionic liquid used in the invention is simple for preparation, low in cost and non-toxic, and has good biological compatibility; the choline ionic liquid catalyst has the advantages of high catalytic activity and good thermal stability, easy recycling, short reaction time, no need of organic solvent and no pollution to the environment. The catalyst is alkaline, can protect the acidic sensitive group in the substrate from damage. The method has simple operation and low cost, and is applicable to industrialized mass production.
Description
Technical field
The invention belongs to the synthesis technical field of Dicoumarin Derivatives, be specifically related to a kind of method that choline-like ionic liquid catalyzes and synthesizes Dicoumarin Derivatives.
Background technology
Dicoumarin Derivatives is distributed widely in the effective constituent in nature various plants with multiple physiologically active, and they show good anticoagulation, the characteristic such as antitumor, antiviral.In Effects of Agricultural Chemicals, coumarin derivatives is developed to s-generation anti-coagulant rodenticide, have efficient, without mutagenesis and carcinogenesis, and vitamin K1 is its special efficacy antidote, adds its safety in utilization.Discovered in recent years Dicoumarin Derivatives can be used as antiseptic-germicide, HIV-1 intergrase, urase and CYP 3A
4inhibitor.Dicoumarin Derivatives not only shows anti-inflammatory and anti-tubercular, and may be used for the fluorescent material such as fluorescent probe or luminous organic material.Report multiple diverse ways to synthesize Dicoumarin Derivatives, comprise molecular iodine, 1,8-diazacyclo [5,4,0] hendecene-7, Manganous chloride tetrahydrate, Et
2alCl
3, POCl
3, sulfonated ionic liquid, Tetrabutyl amonium bromide, zinc (proline(Pro)), solvent-free microwave heating etc.But, these synthetic methods often need to use expensive or poisonous catalyzer, reflux for a long time in volatile organic solvent, temperature of reaction is high, energy consumption is large, product is difficult to purify, and existing acidic catalyst system can make the acid-sensitive group in substrate react, substrate narrow application range.These factors make the production of Dicoumarin Derivatives be difficult to realize large-scale industrial production.
In recent years, ionic liquid is with the character of its uniqueness, as: thermostability, chemical stability, extremely low vapour pressure, nonflammable, can be recycled, the advantage such as designability, become the substitute of the conventional organic solvents of poisonous, inflammable, high volatility, attract wide attention in fields such as medicine, chemical industry.Choline-like ionic liquid Environmental compatibility is good, it is at food, medicine, material, the potential in the fields such as catalysis has caused to be paid close attention to widely, and it is also applied as solvent and catalyzer in the organic synthesis process that some are traditional, but have no report catalyzing and synthesizing the application in Dicoumarin Derivatives.
Summary of the invention
The technical problem that the present invention solves there is provided a kind of method that choline-like ionic liquid catalyzes and synthesizes Dicoumarin Derivatives, choline-like ionic liquid preparation as catalyzer in the method is simple, cheap, there is good biocompatibility and be applicable to large-scale industrial production, can be used for efficient catalytic synthesis Dicoumarin Derivatives.
Technical scheme of the present invention is: choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that: with aromatic aldehyde and 4 hydroxy coumarin for raw material, with the aqueous solution of choline-like ionic liquid for catalyst system and solvent, namely normal heating synthesizes Dicoumarin Derivatives to 25-70 DEG C, and described aromatic aldehyde is
,
,
,
or
, wherein X=H or substituting group, described substituting group is F, Cl, Br, OH, NO
2, CH
3, CF
3, OCH
3or CHO, substituent position is ortho position on phenyl ring, a position or contraposition, and the positively charged ion of described choline-like ionic liquid is
(Choline) or
(DMEA), negatively charged ion is OH
-, CH
3cOO
-, CH
3cH (OH) COO
-, or HSO
4 -.
The mol ratio that choline-like ionic liquid of the present invention catalyzes and synthesizes aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid in the method for Dicoumarin Derivatives is 1:2:0.1-2.
Choline-like ionic liquid of the present invention catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that concrete steps are as follows: the aqueous solution adding aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid in reaction vessel successively, reaction vessel is placed in pre-heated oil bath and is heated to 25-70 DEG C, do not stop to stir, whole reaction process TLC detects, after reaction terminates, be cooled to room temperature, namely obtain Dicoumarin Derivatives with the mixture washing reaction product of water and ethanol.
The aqueous solution catalyst system of choline-like ionic liquid of the present invention can recycle.
The principal reaction equation that choline-like ionic liquid of the present invention catalyzes and synthesizes in the method for Dicoumarin Derivatives is:
，
Wherein R is
,
,
,
or
, X=H or substituting group, described substituting group is F, Cl, Br, OH, NO
2, CH
3, CF
3, OCH
3or CHO, substituent position is ortho position on phenyl ring, a position or contraposition.
The present invention compared with prior art has the following advantages: the choline-like ionic liquid preparation that (1) adopts is simple, cheap, nontoxic, has good biocompatibility; (2) choline-like ionic liquid catalyst activity is high, Heat stability is good, can conveniently recycle; (3) reaction times is short, without the need for machine solvent, avoids the pollution to environment; (4) this catalyzer is in alkalescence, and the acid-sensitive group in substrate can be protected not to be destroyed; (5) the method is easy and simple to handle, with low cost, is applicable to industrialization scale operation.
Embodiment
Be described in further details foregoing of the present invention by the following examples, but this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following embodiment, all technology realized based on foregoing of the present invention all belong to scope of the present invention.
Embodiment 1
In 10ml round-bottomed flask, add phenyl aldehyde (0.5mmol), the aqueous solution (containing ionic liquid 0.75mmol) of choline-like ionic liquid [Choline] [OH] and 4 hydroxy coumarin (1.0mmol) successively, in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 99%.
Embodiment 2
In 10ml round-bottomed flask, add 4-fluorobenzaldehyde (0.5mmol), choline-like ionic liquid [Choline] [CH successively
3cH (OH) COO] the aqueous solution (containing ionic liquid 0.75mmol) and 4 hydroxy coumarin (1.0mmol), in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 90%.
Embodiment 3
In 10ml round-bottomed flask, add 4-chlorobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [DMEA] [HSO successively
4] the aqueous solution (containing ionic liquid 0.75mmol), in 50 DEG C of oil baths, 2h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 90%.
Embodiment 4
In 10ml round-bottomed flask, add 4-bromobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [DMEA] [HSO successively
4] the aqueous solution (containing ionic liquid 0.75mmol), in 70 DEG C of oil baths, 2h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 90%.
Embodiment 5
In 10ml round-bottomed flask, add 4-hydroxy benzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [CH successively
3cOO] the aqueous solution (containing ionic liquid 0.75mmol), in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 90%.
Embodiment 6
In 10ml round-bottomed flask, add Benzaldehyde,2-hydroxy (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [CH successively
3cOO] (containing ionic liquid 0.75mmol), under normal pressure, in 50 DEG C of oil baths, stir 1h, whole reaction process TLC tracking monitor, until reaction terminates.After having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 90%.
Embodiment 7
In 10ml round-bottomed flask, add 4-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [DMEA] [HSO successively
4] (containing ionic liquid 0.75mmol), under normal pressure, in 25 DEG C of oil baths, stir 2h, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 85%.
Embodiment 8
In 10ml round-bottomed flask, add 3-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [OH] (containing ionic liquid 0.75mmol) successively, in 50 DEG C of oil baths, 2h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 93%.
Embodiment 9
In 10ml round-bottomed flask, add 2-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [CH successively
3cOO] (containing ionic liquid 0.75mmol), under normal pressure, in 50 DEG C of oil baths, stir 2h, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 70%.
Embodiment 10
In 10ml round-bottomed flask, add 4-tolyl aldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [CH successively
3cOO] (containing ionic liquid 0.75mmol), under normal pressure, in 50 DEG C of oil baths, stir 2h, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 88%.
Embodiment 11
In 10ml round-bottomed flask, add 4-trifluro benzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [CH successively
3cOO] (containing ionic liquid 0.75mmol), under normal pressure, in 50 DEG C of oil baths, stir 2h, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 85%.
Embodiment 12
In 10ml round-bottomed flask, add 4-methoxybenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [DMEA] [HSO successively
4] the aqueous solution (containing ionic liquid 0.75mmol), in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 95%.
Embodiment 13
In 10ml round-bottomed flask, add the aqueous solution (containing ionic liquid 0.75mmol) of 3-methoxy-4-hydroxybenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [OH] successively, in 50 DEG C of oil baths, 2h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 93%.
Embodiment 14
In 10ml round-bottomed flask, add Pyridine-4-Carboxaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [DMEA] [HSO successively
4] the aqueous solution (containing ionic liquid 0.05mmol), in 50 DEG C of oil baths, 2h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 77%.
Embodiment 15
In 10ml round-bottomed flask, add the aqueous solution (containing ionic liquid 0.75mmol) of furfural (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [OH] successively, in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 98%.
Embodiment 16
In 10ml round-bottomed flask, add the aqueous solution (containing ionic liquid 1.0mmol) of phenylacrolein (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [OH] successively, in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 87%.
Embodiment 17
In 10ml round-bottomed flask, add the aqueous solution (containing ionic liquid 0.75mmol) of piperonylaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline-like ionic liquid [Choline] [OH] successively, in 50 DEG C of oil baths, 3h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 95%.
Embodiment 18
In 10ml round-bottomed flask, add the aqueous solution (containing ionic liquid 0.75mmol) of phenyl aldehyde (2.0mmol), 4 hydroxy coumarin (4.0mmol) and choline-like ionic liquid [Choline] [OH] successively, in 50 DEG C of oil baths, 1h is stirred under normal pressure, whole reaction process TLC tracking monitor, until reaction terminates, after having reacted, be cooled to room temperature, can obtain target product with the mixture washing reaction mixture of water and ethanol, productive rate is 98%.
With embodiment 18 for probe reaction, make the active replica test of catalyzer choline-like ionic liquid, choline-like ionic liquid reuses 5 times, and product yield is in table 1.
Table 1 choline-like ionic liquid recycles situation
| Entry | Reaction time(h) | Yield(％) |
| 1 | 1 | 98 |
| 2 | 1 | 97 |
| 3 | 1 | 96 |
| 4 | 1 | 97 |
| 5 | 1 | 96 |
As can be seen from Table 1: the aqueous solution catalyst system of choline-like ionic liquid is after recycling and preparing and recycle 5 times in product process, productive rate has no obvious reduction, illustrates that choline-like ionic liquid can be recycled in the process catalyzing and synthesizing Dicoumarin Derivatives.
Embodiment above describes ultimate principle of the present invention, principal character and advantage; the technician of the industry should understand; the present invention is not restricted to the described embodiments; what describe in above-described embodiment and specification sheets just illustrates principle of the present invention; under the scope not departing from the principle of the invention; the present invention also has various changes and modifications, and these changes and improvements all fall into the scope of protection of the invention.
Claims (5)
1. choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that: with aromatic aldehyde and 4 hydroxy coumarin for raw material, with the aqueous solution of choline-like ionic liquid for catalyst system and solvent, namely normal heating synthesizes Dicoumarin Derivatives to 25-70 DEG C, and described aromatic aldehyde is
,
,
,
or
, wherein X=H or substituting group, described substituting group is F, Cl, Br, OH, NO
2, CH
3, CF
3, OCH
3or CHO, substituent position is ortho position on phenyl ring, a position or contraposition, and the positively charged ion of described choline-like ionic liquid is
or
, negatively charged ion is OH
-, CH
3cOO
-, CH
3cH (OH) COO
-or HSO
4 -.
2. choline-like ionic liquid according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that: the mol ratio of described aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid is 1:2:0.1-2.
3. choline-like ionic liquid according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that concrete steps are as follows: the aqueous solution adding aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid in reaction vessel successively, reaction vessel is placed in pre-heated oil bath and is heated to 25-70 DEG C, do not stop to stir, whole reaction process TLC detects, after reaction terminates, be cooled to room temperature, namely obtain Dicoumarin Derivatives with the mixture washing reaction product of water and ethanol.
4. choline-like ionic liquid according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that: the aqueous solution catalyst system of described choline-like ionic liquid can recycle.
5. choline-like ionic liquid according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterized in that: the principal reaction equation that described choline-like ionic liquid catalyzes and synthesizes in the method for Dicoumarin Derivatives is:
，
Wherein R is
,
,
,
or
, X=H or substituting group, described substituting group is F, Cl, Br, OH, NO
2, CH
3, CF
3, OCH
3or CHO, substituent position is ortho position on phenyl ring, a position or contraposition.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529987A (en) * | 2014-12-04 | 2015-04-22 | 中国人民解放军第四军医大学 | 4-hydroxyl bishydroxycoumarin compound and application thereof |
| CN105949240A (en) * | 2016-05-13 | 2016-09-21 | 河南师范大学 | Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid |
Citations (3)
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|---|---|---|---|---|
| CN102911151A (en) * | 2012-07-12 | 2013-02-06 | 盐城师范学院 | Method for water-phase synthesis of benzoxanthene derivatives |
| CN103232426A (en) * | 2013-05-15 | 2013-08-07 | 台州学院 | Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis |
| CN103613573A (en) * | 2013-11-11 | 2014-03-05 | 河南师范大学 | Method for synthesizing coumarin and derivatives thereof under catalysis of choline ionic liquids |
-
2014
- 2014-09-19 CN CN201410480624.8A patent/CN104311521B/en not_active Expired - Fee Related
Patent Citations (3)
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| CN102911151A (en) * | 2012-07-12 | 2013-02-06 | 盐城师范学院 | Method for water-phase synthesis of benzoxanthene derivatives |
| CN103232426A (en) * | 2013-05-15 | 2013-08-07 | 台州学院 | Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis |
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Non-Patent Citations (14)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529987A (en) * | 2014-12-04 | 2015-04-22 | 中国人民解放军第四军医大学 | 4-hydroxyl bishydroxycoumarin compound and application thereof |
| CN105949240A (en) * | 2016-05-13 | 2016-09-21 | 河南师范大学 | Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid |
| CN105949240B (en) * | 2016-05-13 | 2017-10-31 | 河南师范大学 | 4 phosphonic acids 1,5 of ionic liquid-catalyzed synthesis replace the method for 1,2,3 triazole compounds |
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