CN104311521B - Choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives - Google Patents

Choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives Download PDF

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CN104311521B
CN104311521B CN201410480624.8A CN201410480624A CN104311521B CN 104311521 B CN104311521 B CN 104311521B CN 201410480624 A CN201410480624 A CN 201410480624A CN 104311521 B CN104311521 B CN 104311521B
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choline
ionic liquid
synthesizes
catalyzes
dicoumarin
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CN104311521A (en
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朱安莲
白淑坤
李凌君
王键吉
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Henan Normal University
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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
    • 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
    • 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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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of method that choline-like ionic liquid catalyzes and synthesizes Dicoumarin Derivatives.Technical scheme main points are: choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives, with aromatic aldehyde and 4 Hydroxycoumarins as raw material, with the aqueous solution of choline-like ionic liquid as catalyst system and catalyzing with solvent, normal heating to 25 70 DEG C i.e. synthesizes Dicoumarin Derivatives.Choline-like ionic liquid of the present invention preparation is simple, cheap, nontoxic, has good biocompatibility；Choline-like ionic liquid catalyst activity is high, and Heat stability is good can conveniently recycle；Response time is short, it is not necessary to organic solvent, it is to avoid pollution to environment；This catalyst is alkalescence, and the acid-sensitive group in substrate can be protected not to be destroyed；The method is easy and simple to handle, with low cost, is suitable for industrialization large-scale production.

Description

Choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives
Technical field
The invention belongs to the synthesis technical field of Dicoumarin Derivatives, be specifically related to a kind of choline-like ionic liquid and urge The method being combined to Dicoumarin Derivatives.
Background technology
Dicoumarin Derivatives is the effective one-tenth being distributed widely in nature various plants and having multiple physiologically active Point, they show the characteristics such as preferable anticoagulation, antitumor, antiviral.In Effects of Agricultural Chemicals, coumarin derivative It is developed to second filial generation anti-coagulant rodenticide, has efficiently, without mutagenesis and carcinogenesis, and vitamin K1 is its specially good effect Antidote, adds its safety in utilization.Discovered in recent years Dicoumarin Derivatives can be integrated as antibacterial, HIV-1 Enzyme, urase and CYP 3A4Inhibitor.Dicoumarin Derivatives not only shows antiinflammatory and anti-tubercular, and can use In the fluorescent material such as fluorescent probe or luminous organic material.It has been reported multiple different method to synthesize dicoumarol class chemical combination Thing, including molecular iodine, 1,8-diazacyclo [5,4,0] hendecene-7, manganese chloride, Et2AlCl3、POCl3, sulfonated ionic liquid Body, tetrabutyl ammonium bromide, zinc (proline), solvent-free microwave heating etc..But, these synthetic methods generally require use price Expensive or poisonous catalyst, refluxes in volatile organic solvent for a long time, and reaction temperature is high, energy consumption is big, and product is difficult to Purify, and existing acidic catalyst system can make the acid-sensitive group in substrate react, substrate narrow application range.This A little factors make the production of Dicoumarin Derivatives be difficult to large-scale industrial production.
In recent years, ionic liquid is with the character of its uniqueness, such as: heat stability, chemical stability, extremely low vapour pressure, no Inflammable, can be recycled, the advantage such as designability so that it is become the replacement of the conventional organic solvents of poisonous, inflammable, high volatility Product, attract wide attention in fields such as medicine, chemical industry.Choline-like ionic liquid Environmental compatibility is good, and it is medical at food, Material, the potential in the fields such as catalysis has caused to be paid close attention to widely, and it is the most traditional at some as solvent and catalyst Organic synthesis during be applied, but the application in catalyzing and synthesizing Dicoumarin Derivatives has no report.
Summary of the invention
Present invention solves the technical problem that there is provided a kind of choline-like ionic liquid catalyzes and synthesizes dicoumarol class chemical combination The method of thing, in the method, the choline-like ionic liquid as catalyst is prepared simple, cheap, has good biofacies Capacitive and applicable large-scale industrial production, can be used for efficient catalytic synthesis Dicoumarin Derivatives.
The technical scheme is that the method that choline-like ionic liquid catalyzes and synthesizes Dicoumarin Derivatives, it is special Levy and be: with aromatic aldehyde and 4 hydroxy coumarin as raw material, with the aqueous solution of choline-like ionic liquid as catalyst system and catalyzing with solvent, Normal heating i.e. synthesizes Dicoumarin Derivatives to 25-70 DEG C, and described aromatic aldehyde is、、、Or, wherein X=H or substituent group, Described substituent group is F, Cl, Br, OH, NO2、CH3、CF3、OCH3Or CHO, the position of substituent group is the ortho position on phenyl ring, meta Or para-position, the cation of described choline-like ionic liquid is(Choline) or(DMEA), anion is OH-、CH3COO-、CH3CH(OH)COO-, or HSO4 -。
Choline-like ionic liquid of the present invention catalyzes and synthesizes aromatic aldehyde, 4-hydroxyl in the method for Dicoumarin Derivatives The mol ratio of butylcoumariii and choline-like ionic liquid is 1:2:0.1-2.
Choline-like ionic liquid of the present invention catalyzes and synthesizes the method for Dicoumarin Derivatives, it is characterised in that tool Body step is as follows: be sequentially added into the aqueous solution of aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid in reaction vessel, will Reaction vessel is placed in pre-heated oil bath and is heated to 25-70 DEG C, does not stop stirring, and whole course of reaction TLC detects, instead After should terminating, it is cooled to room temperature, i.e. obtains Dicoumarin Derivatives with the mixture washing reaction product of water and ethanol.
The aqueous solution catalyst system and catalyzing of choline-like ionic liquid of the present invention can recycle.
Choline-like ionic liquid of the present invention catalyzes and synthesizes the dominant response in the method for Dicoumarin Derivatives Equation is:
,
Wherein R is、、、Or, X =H or substituent group, described substituent group is F, Cl, Br, OH, NO2、CH3、CF3、OCH3Or CHO, the position of substituent group is on phenyl ring Ortho position, meta or para position.
The present invention compared with prior art has the advantage that the choline-like ionic liquid preparation that (1) is used is simple, valency Lattice are cheap, nontoxic, have good biocompatibility；(2) choline-like ionic liquid catalyst activity is high, heat stability Good, can conveniently recycle；(3) response time is short, it is not necessary to organic solvent, it is to avoid pollution to environment；(4) this catalysis Agent is 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 suitable for Industrialization large-scale production.
Detailed description of the invention
By the following examples the foregoing of the present invention is described in further details, but this should be interpreted as this The scope inventing above-mentioned theme is only limitted to below example, and all technology realized based on foregoing of the present invention belong to this Bright scope.
Embodiment 1
In 10ml round-bottomed flask, it is sequentially added into benzaldehyde (0.5mmol), choline-like ionic liquid [Choline] [OH] Aqueous solution (containing ionic liquid 0.75mmol) and 4 hydroxy coumarin (1.0mmol), under normal pressure in 50 DEG C of oil baths stir 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, it is cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, and productivity is 99%.
Embodiment 2
In 10ml round-bottomed flask, it is sequentially added into 4-fluorobenzaldehyde (0.5mmol), choline-like ionic liquid [Choline] [CH3CH (OH) COO] aqueous solution (containing ionic liquid 0.75mmol) and 4 hydroxy coumarin (1.0mmol), under normal pressure 50 DEG C of oil baths are stirred 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room Temperature, i.e. can get target product with the mixture washing reaction mixture of water and ethanol, and productivity is 90%.
Embodiment 3
In 10ml round-bottomed flask, be sequentially added into 4-chlorobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and Choline-like ionic liquid [DMEA] [HSO4] aqueous solution (containing ionic liquid 0.75mmol), stir in 50 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 90%.
Embodiment 4
In 10ml round-bottomed flask, be sequentially added into 4-bromobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and Choline-like ionic liquid [DMEA] [HSO4] aqueous solution (containing ionic liquid 0.75mmol), stir in 70 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 90%.
Embodiment 5
In 10ml round-bottomed flask, it is sequentially added into 4-hydroxy benzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [CH3COO] aqueous solution (containing ionic liquid 0.75mmol), at 50 DEG C under normal pressure Oil bath is stirred 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room temperature, use The mixture washing reaction mixture of water and ethanol i.e. can get target product, and productivity is 90%.
Embodiment 6
In 10ml round-bottomed flask, it is sequentially added into Benzaldehyde,2-hydroxy (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [CH3COO] (containing ionic liquid 0.75mmol), stir in 50 DEG C of oil baths under normal pressure Mix 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates.After having reacted, it is cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 90%.
Embodiment 7
In 10ml round-bottomed flask, it is sequentially added into 4-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [DMEA] [HSO4] (containing ionic liquid 0.75mmol), under normal pressure, in 25 DEG C of oil baths, stir 2h, Whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room temperature, with water and the mixing of ethanol Thing washing reaction mixture i.e. can get target product, and productivity is 85%.
Embodiment 8
In 10ml round-bottomed flask, it is sequentially added into 3-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [OH] (containing ionic liquid 0.75mmol), under normal pressure, in 50 DEG C of oil baths, stir 2h, Whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room temperature, with water and the mixing of ethanol Thing washing reaction mixture i.e. can get target product, and productivity is 93%.
Embodiment 9
In 10ml round-bottomed flask, it is sequentially added into 2-nitrobenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [CH3COO] (containing ionic liquid 0.75mmol), stir in 50 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 70%.
Embodiment 10
In 10ml round-bottomed flask, it is sequentially added into 4-tolyl aldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [CH3COO] (containing ionic liquid 0.75mmol), stir in 50 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 88%.
Embodiment 11
In 10ml round-bottomed flask, it is sequentially added into 4-trifluro benzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) With choline-like ionic liquid [Choline] [CH3COO] (containing ionic liquid 0.75mmol), stir in 50 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 85%.
Embodiment 12
In 10ml round-bottomed flask, it is sequentially added into 4-methoxybenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) with choline-like ionic liquid [DMEA] [HSO4] aqueous solution (containing ionic liquid 0.75mmol), under normal pressure 50 DEG C of oil baths are stirred 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room Temperature, i.e. can get target product with the mixture washing reaction mixture of water and ethanol, and productivity is 95%.
Embodiment 13
In 10ml round-bottomed flask, it is sequentially added into 3-methoxy-4-hydroxybenzaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and the aqueous solution (containing ionic liquid 0.75mmol) of choline-like ionic liquid [Choline] [OH], under normal pressure 50 DEG C of oil baths are stirred 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room Temperature, i.e. can get target product with the mixture washing reaction mixture of water and ethanol, and productivity is 93%.
Embodiment 14
In 10ml round-bottomed flask, be sequentially added into Pyridine-4-Carboxaldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and Choline-like ionic liquid [DMEA] [HSO4] aqueous solution (containing ionic liquid 0.05mmol), stir in 50 DEG C of oil baths under normal pressure Mix 2h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, be cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, productivity is 77%.
Embodiment 15
In 10ml round-bottomed flask, it is sequentially added into furfural (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline The aqueous solution (containing ionic liquid 0.75mmol) of ionic liquid [Choline] [OH], stirs 1h under normal pressure in 50 DEG C of oil baths, Whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, is cooled to room temperature, with water and the mixing of ethanol Thing washing reaction mixture i.e. can get target product, and productivity is 98%.
Embodiment 16
In 10ml round-bottomed flask, it is sequentially added into cinnamic aldehyde (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline The aqueous solution (containing ionic liquid 1.0mmol) of class ionic liquid [Choline] [OH], stirs under normal pressure in 50 DEG C of oil baths 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, it is cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, and productivity is 87%.
Embodiment 17
In 10ml round-bottomed flask, it is sequentially added into piperonal (0.5mmol), 4 hydroxy coumarin (1.0mmol) and choline The aqueous solution (containing ionic liquid 0.75mmol) of class ionic liquid [Choline] [OH], stirs under normal pressure in 50 DEG C of oil baths 3h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, it is cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, and productivity is 95%.
Embodiment 18
In 10ml round-bottomed flask, it is sequentially added into benzaldehyde (2.0mmol), 4 hydroxy coumarin (4.0mmol) and choline The aqueous solution (containing ionic liquid 0.75mmol) of class ionic liquid [Choline] [OH], stirs under normal pressure in 50 DEG C of oil baths 1h, whole course of reaction TLC tracking and monitoring, until reaction terminates, after having reacted, it is cooled to room temperature, with water and ethanol Mixture washing reaction mixture i.e. can get target product, and productivity is 98%.
With embodiment 18 as probe reaction, make the active replica test of catalyst choline-like ionic liquid, choline from Sub-liquid is reused 5 times, and product yield is shown 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 and catalyzing of choline-like ionic liquid is during product is prepared in recycling After recycling 5 times, productivity has no substantially reduction, illustrates that choline-like ionic liquid is catalyzing and synthesizing Dicoumarin Derivatives During can be recycled.
Embodiment above describes the ultimate principle of the present invention, principal character and advantage, the technical staff of the industry should Understanding, the present invention is not restricted to the described embodiments, and the simply explanation present invention's described in above-described embodiment and description is former Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within The scope of protection of the invention.

Claims (4)

1. the method that choline-like ionic liquid catalyzes and synthesizes Dicoumarin Derivatives, it is characterised in that: with aromatic aldehyde and 4-hydroxyl Butylcoumariii is raw material, and with the aqueous solution of choline-like ionic liquid as catalyst system and catalyzing with solvent, normal heating i.e. closes to 25-70 DEG C Becoming Dicoumarin Derivatives, the mol ratio of described aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid is 1:2: 0.1-2, described aromatic aldehyde is、、、 Or, wherein X=H or substituent group, described substituent group is F, Cl, Br, OH, NO2、CH3、CF3、OCH3Or CHO, the position of substituent group is the ortho position on phenyl ring, meta or para position, and the cation of described choline-like ionic liquid isOr, anion is OH-、CH3COO-、CH3CH(OH)COO-Or HSO4 -。
Choline-like ionic liquid the most according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, its feature It is to specifically comprise the following steps that the water being sequentially added into aromatic aldehyde, 4 hydroxy coumarin and choline-like ionic liquid in reaction vessel Solution, is placed in reaction vessel in pre-heated oil bath and is heated to 25-70 DEG C, does not stop stirring, whole course of reaction TLC Detection, after reaction terminates, is cooled to room temperature, i.e. obtains dicoumarol class chemical combination with the mixture washing reaction product of water and ethanol Thing.
Choline-like ionic liquid the most according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, its feature It is: the aqueous solution catalyst system and catalyzing of described choline-like ionic liquid can recycle.
Choline-like ionic liquid the most according to claim 1 catalyzes and synthesizes the method for Dicoumarin Derivatives, its feature It is: the dominant response equation that described choline-like ionic liquid catalyzes and synthesizes in the method for Dicoumarin Derivatives is:
,
Wherein R is、、、Or, X=H or Substituent group, described substituent group is F, Cl, Br, OH, NO2、CH3、CF3、OCH3Or CHO, the position of substituent group is the neighbour on phenyl ring Position, meta or para position.
CN201410480624.8A 2014-09-19 2014-09-19 Choline-like ionic liquid catalyzes and synthesizes the method for Dicoumarin Derivatives Expired - Fee Related CN104311521B (en)

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