CN108558807A - The method of one pot process cumarin base chalcone compounds - Google Patents
The method of one pot process cumarin base chalcone compounds Download PDFInfo
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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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
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Abstract
The method of one pot process cumarin base chalcone compounds, belongs to technical field of organic synthesis, building-up process is as follows：Salicylide and ethyl acetoacetate are added into reaction bulb, under the conditions of 05 DEG C, sequentially add diethylamine and pyridine, ethyl alcohol, R CHO and piperidines are sequentially added after stirring 10 ~ 30min in the case where 10 DEG C of ＜, it is heated to reflux to the reaction was complete, is cooled to room temperature, solvent is evaporated off, silica gel column chromatography detaches, and obtains target compound, wherein the molar ratio of salicylide, ethyl acetoacetate and R CHO is 1 ︰（1~1.2）︰（1~1.2）, R is aryl.The present invention first uses solvent-free reaction that cumarin is made, and is not isolated and directly synthesizes cumarin base chalcone in ethanol medium；The first step is catalyzed using pyridine and diethylamine catalysis reaction, second step with piperidines, and pyridine and diethylamine will not react second step and generate harmful effect, and the catalyst of the opposite first step can also be catalyzed second step reaction.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of one pot process cumarin base chalcone compounds
Method.
Background technology
Chalcone, that is, α, alpha, beta-unsaturated ketone are one of structure type important in natural organic molecules, and a variety of days of synthesis
The important organic intermediate of right object and drug, chalcone and its derivative are the products that cross aldol condensation occurs for aromatic aldehyde ketone,
Its entitled 1,3- diphenylprops ketenes of chemistry.Chalcone compounds are widely present in nature, using it as the chemical combination of parent
Object is present in a variety of natural fronds such as Radix Glycyrrhizae, safflower.Due to its molecular machinery have larger flexibility, can from it is different by
Body combines, therefore with extensive bio-pharmacology activity, such as：It is antitumor, inhibit and understand oxygen radical, is antibacterial, antiviral, anti-
Ulcer conciliates the bio-pharmacologies such as spasm activity, due to its unique plasticity structure, has caused the dense of researcher in recent years
Thick research interest.
Two step cascade reaction of one kettle way is one of forward position and hot spot of current organic synthesis research, in the full conjunction of natural products
At, combinatorial chemistry, heterocyclic compound synthesis etc. fields have a wide range of applications.The intermediate of one kettle way cascade reaction need not divide
From can carry out next step reaction, to simplify operating procedure, can be used for designing unstable reactive intermediate；Series connection
Reaction carries out in same environment, reduces the generation of solvent, the dosage of eluant, eluent, type and by-product, is conducive to protection ring
Border and reduce cost；Cascade reaction need not carry out intermediate separation, be conducive to improve working efficiency, save the time；Series connection is anti-
Multiple covalent bonds can be formed during answering, and can effectively improve yield relative to distribution reaction.Thus cumarin base is looked into
It is necessary to further improve or inquire into new preparation process for the preparation process pole of your ketone compounds.
Invention content
The purpose of the present invention is to provide a kind of methods of one pot process cumarin base chalcone compounds, with bigcatkin willow
Aldehyde, ethyl acetoacetate and aromatic aldehyde are raw material, and a series of cumarin base chalcones are synthesized using one kettle way cascade reaction
Object is closed, efficiency and yield have larger promotion compared with the method for fractional steps.
The technical solution adopted by the present invention is as follows：
The method of one pot process cumarin base chalcone compounds, building-up process are as follows：
Salicylide is added into reaction bulb and ethyl acetoacetate sequentially adds under the conditions of 0-5 DEG C (i.e. in ice-water bath)
Diethylamine and pyridine, at 10 DEG C of ＜ (i.e. in ice-water bath) after 10~30min of stirring (the reaction was complete for TLC tracking and monitorings) successively
Ethyl alcohol, R-CHO and piperidines is added, is heated to reflux to the reaction was complete (about 6h), is cooled to room temperature, solvent, silica gel column chromatography is evaporated off
Separation, obtains target compoundWherein, the molar ratio of salicylide, ethyl acetoacetate and R-CHO
For 1 ︰, (1~1.2) ︰ (1~1.2), R is aryl.
Preferably, the molar ratio of salicylide, ethyl acetoacetate and R-CHO are 1 ︰, 1 ︰ 1.1.
Specifically, the dosage of each material is in reaction：Salicylide 10mmol, ethyl acetoacetate 10mmol, diethylamine
0.05mL, pyridine 0.05mL, ethyl alcohol 20mL, aromatic aldehyde 11mmol, piperidines 0.3mL, meanwhile, R is
Wherein, when silica gel column chromatography detaches, the mixture with petroleum ether and ethyl acetate that volume ratio is 4 ︰, 1 to 8 ︰ 1 is
Eluant, eluent.
The present invention first uses solvent-free reaction that cumarin is made, and is not isolated and directly synthesizes tonka-bean in ethanol medium
Plain base chalcone；Knoevenagel reactions are occurred using pyridine and diethylamine catalysis in synthesizing coumarin, are then situated between in ethyl alcohol
It is catalyzed with piperidines in matter and acetal ketone reaction occurs, after the completion of first step reaction, piperidines catalysis second step reaction is added, is added before this
Pyridine and diethylamine second step will not be reacted and generate harmful effect, the catalyst of the opposite first step can also be catalyzed second step
Reaction, to make second step reaction more smoothly carry out.In conclusion the synthesis of cumarin base chalcone is connected using separation is not added with
Continuous its efficiency and yield of operating has larger promotion compared with the method for fractional steps.
Description of the drawings
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of 3- acetyl butylcoumariiis；
Fig. 2 is the carbon-13 nmr spectra figure of 3- acetyl butylcoumariiis；
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of the compound 1；
Fig. 4 is the carbon-13 nmr spectra figure of the compound 1；
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram of the compound 2；
Fig. 6 is the carbon-13 nmr spectra figure of the compound 2；
Fig. 7 is the hydrogen nuclear magnetic resonance spectrogram of the compound 3；
Fig. 8 is the carbon-13 nmr spectra figure of the compound 3；
Fig. 9 is the hydrogen nuclear magnetic resonance spectrogram of the compound 4；
Figure 10 is the carbon-13 nmr spectra figure of the compound 4；
Figure 11 is the hydrogen nuclear magnetic resonance spectrogram of the compound 5；
Figure 12 is the carbon-13 nmr spectra figure of the compound 5；
Figure 13 is the hydrogen nuclear magnetic resonance spectrogram of the compound 6；
Figure 14 is the carbon-13 nmr spectra figure of the compound 6.
Specific implementation mode
In order to keep the technical purpose, technical solution and advantageous effect of the present invention clearer, below in conjunction with the accompanying drawings and specifically
Embodiment is further illustrated technical scheme of the present invention.
Embodiment 1
Major experimental reagent and instrument：Salicylide, ethyl acetoacetate, diethylamine, pyridine, piperidines, benzaldehyde, 4- methoxies
Benzaldehyde, 3- nitrobenzaldehydes, Benzaldehyde,2-hydroxy, 4- hydroxy benzaldehydes, vanillic aldehyde, petroleum ether, dichloro, ethyl acetate,
Ethyl alcohol, 300-400 mesh silica gel, electronic balance, Rotary Evaporators, electromagnetic heating set, Bruker Avance III 600MHz cores
Resonance spectrometer (Bruker companies of the U.S.).
The synthetic route of cumarin base chalcone：In the round-bottomed flask of 25mL, be added 10mmol salicylides (1.22g, 1.04mL) and
10mmol ethyl acetoacetates (1.30g, 1.27mL), ice-water bath is cooled under the conditions of 0-5 DEG C, is slowly added to diethylamine successively
(0.05mL) and pyridine (0.05mL), continues in ice bath (maintaining reaction temperature later<10 DEG C) 10~30min of stirring, around here
Reaction mixture gradually becomes yellow solid.Aromatic aldehyde (the R- for then sequentially adding ethyl alcohol (20mL), being connected with different substituents
CHO, 11mmol) and piperidines (0.3mL), heating reflux reaction 6h, obtain corresponding cumarin chalcone target compound.Reaction
After be cooled to room temperature, after removing solvent under reduced pressure, detached with silica gel column chromatography, obtain the production of corresponding cumarin base chalcone target
Object, yield 68.3%-87.1%.
Cumarin base chalcone target product structure：
By BrukerAvance III 600MHz nuclear magnetic resonance chemical analysers (Bruker companies of the U.S.) to 3- acetyl basic notes
Legumin, 1 to 6 structure of gained target compound are detected, and nucleus magnetic hydrogen spectrum and carbon spectrum are as shown in attached drawing 1 to 14.
The structural characterization data of 3- acetyl butylcoumariii and cumarin base chalcone：
3- acetyl butylcoumariiis obtain m.p.81.6-83.5 DEG C of light yellow solid with ethyl alcohol recrystallization.1H NMR
(600MHz,CDCl3)δ:8.52(s,1H),7.65-7.67(m,2H),7.34-7.39(m,2H),2.74(s,3H).13C NMR
(125MHz,CDCl3)δ:195.5,159.3,155.4,147.5,134.4,130.3,125.0,124.5,118.3,116.7,
30.6.
3-cinnamoyl-2H-chromen-2-one (1) is with petrol ether/ethyl acetate (v:V=8:1) it is eluant, eluent, obtains
To m.p.131.4-133.7 DEG C of light yellow solid.1H NMR(600MHz,CDCl3)δ:8.59(s,1H),7.86-7.97(m,
2H), 7.65-7.69 (m, 4H), 7.39-7.42 (m, 4H), 7.36 (td, J=12.0Hz, J=1.2Hz, 1H)13C NMR
(125MHz,CDCl3)δ:186.5,159.3,155.3,148.1,145.1,134.8,134.3,130.9,130.1,128.9,
125.3,125.0,123.9,118.6,116.7.
(E) -3- (3- (3-nitrophenyl) acryloyl) -2H-chromen-2-one (2) is with petroleum ether/acetic acid second
Ester (v:V=8:1) it is eluant, eluent, obtains m.p.205.7-207.2 DEG C of yellow solid.1H NMR(600MHz,DMSO-d6)δ:
8.71 (s, 1H), 8.60 (t, J=1.8Hz, 1H), 8.30 (dd, J=8.4Hz, J=1.2Hz, 1H), 8.25 (d, J=7.8Hz,
1H), 7.97 (dd, J=7.8Hz, J=1.2Hz, 1H), 7.91 (d, J=16.2Hz, 1H), 7.76-7.80 (m, 2H), 7.52
(d, J=7.8Hz, 1H), 7.43-7.48 (m, 2H)13C NMR(125MHz,DMSO-d6)δ:188.0,158.9,155.0,
148.8,147.6,142.0,136.8,135.0,134.8,131.1,131.0,127.9,125.9,125.5,125.4,
123.6,118.9,116.8.
(E) -3- (3- (4-methoxyphenyl) acryloyl) -2H-chromen-2-one (3) is with petroleum ether/acetic acid
Ethyl ester (v:V=6:1) it is eluant, eluent, obtains m.p.187.1-189.2 DEG C of faint yellow solid.1H NMR(600MHz,CDCl3)δ:
8.58(s,1H),7.84-7.85(m,2H),7.56(m,4H),7.32-7.41(m,2H),6.92-6.95(m,2H),3.86(s,
3H).13C NMR(125MHz,CDCl3)δ:186.4,162.2,159.6,155.4,148.0,145.2,134.3,131.0,
130.2,127.8,125.7,125.2,121.9,118.8,116.9,114.6,55.7.
(E) -3- (3- (2-hydroxyphenyl) acryloyl) -2H-chromen-2-one (4) is with petroleum ether/acetic acid
Ethyl ester (v:V=4:1) it is eluant, eluent, obtains m.p.165.2-167.1 DEG C of orange/yellow solid.1H NMR(600MHz,DMSO-d6)
δ:10.36(s,1H),8.67(s,1H),7.95-8.00(m,2H),7.73-7.76(m,2H),7.64-7.65(m,1H),7.49
(d, J=7.8Hz, 1H), 7.43 (t, J=7.2Hz, 1H), 7.29 (t, J=7.8Hz, 1H), 6.94 (d, J=7.8Hz, 1H),
6.88 (t, J=7.8Hz, 1H)13C NMR(125MHz,DMSO-d6)δ:187.7,158.9,158.0,154.9,147.3,
140.2,134.6,132.8,130.9,129.5,126.2,125.4,124.4,121.6,120.0,118.9,116.8,
116.7.
(E) -3- (3- (4-hydroxyphenyl) acryloyl) -2H-chromen-2-one (5) is with petroleum ether/acetic acid
Ethyl ester (v:V=4:1) it is eluant, eluent, obtains m.p.197.5-198.8 DEG C of orange/yellow solid.1H NMR(600MHz,DMSO-d6)
δ:10.18 (s, 1H), 8.63 (s, 1H), 7.94 (d, J=15.6Hz, 1H), 7.73 (t, J=7.2Hz, 1H), 7.62 (t, J=
16.8Hz, 2H), 7.49 (t, J=8.1Hz, 2H), 7.41-7.46 (m, 2H), 6.85 (d, J=17.4Hz, 2H)13C NMR
(125MHz,DMSO-d6)δ:186.8,160.3,158.3,154.2,146.3,144.8,133.8,130.8,130.2,
125.6,125.4,124.8,121.1,118.3,116.0,115.9.
(E) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-chromen-2-one (6) is with stone
Oily ether/ethyl acetate (v:V=4:1) it is eluant, eluent, obtains m.p.171.1-173.7 DEG C of Orange red solid.1H NMR
(600MHz,DMSO-d6)δ:9.80 (s, 1H), 8.59 (s, 1H), 7.93 (dd, J=7.8Hz, J=1.2Hz, 1H), 7.74
(td, J=7.8Hz, J=1.2Hz, 1H), 7.70 (d, J=15.6Hz, 1H), 7.49 (d, J=8.4Hz, 1H), 7.42-7.46
(m, 2H), 7.34 (d, J=1.8Hz, 1H), 7.24 (dd, J=7.8Hz, J=1.8Hz, 1H), 6.85 (d, J=7.8Hz, 1H),
3.84(s,3H).13C NMR(125MHz,DMSO-d6)δ187.5,158.4,154.3,150.0,147.9,145.9,145.6,
133.9,130.2,126.1,125.9,124.9,123.5,121.7,118.4,116.2,115.8,112.0,55.7.
Comparative example 1
Cumarin base chalcone substep synthesizes：
1. the synthesis of 3- acetyl butylcoumariiis：
In the round-bottomed flask of 100mL, 100mmol salicylides (12.21g, 10.43mL) and 100mmol acetyl second is added
Acetoacetic ester (13.01g, 12.65mL), ice-water bath is cooled under the conditions of 0-5 DEG C, is slowly added to 0.5mL diethylamine and 0.5mL pyrroles successively
Simultaneously maintaining reaction temperature is stirred in pyridine<10 DEG C extremely the reaction was complete (10~30min), and it is solid to increasingly generate yellow for reaction mixture around here
Body, last whole system become solid.After reaction, ethyl alcohol recrystallization is directly added in the reaction system, it is dry, it obtains light
Yellow flat crystal 16.92g, yield 90% have light fragrance.
2. the synthesis of cumarin base chalcone：
In the round-bottomed flask of 50mL, 10mmol 3- acetyl butylcoumariiis (1.88g) are added, 11mmol is connected with difference and takes
The aromatic aldehyde (R-CHO) of Dai Ji and the ethyl alcohol and 0.3mL piperidines of 20mL 95%, heating reflux reaction 6h, reaction is mixed around here
Closing liquid color becomes peony, and has solid generation.It is cooled to room temperature after reaction, after removing solvent under reduced pressure, with silica gel column layer
Analysis separation, obtains corresponding cumarin base chalcone target product, yield 72.8%-89.3%.
In cumarin base chalcone substep building-up process, first, salicylide is with ethyl acetoacetate in organic base catalytic
Lower generation Knoevenagel reactions, obtain 3- acetyl butylcoumariiis, then, 3- acetyl butylcoumariii and aldehyde are still in organic base
In the presence of carry out aldol reaction, obtain cumarin base chalcone.Meanwhile in synthetic operation, it is observed that following two
Kind phenomenon：1, reaction dissolvent, the first step use solvent-free reaction, hereafter synthesize and completed in ethanol medium；2, in terms of catalyst,
First using mixing organic base, second step be then organic base piperidines catalysis under carry out, and the first step reaction after the completion of
Ethyl alcohol can be directly added into and carry out second step reaction.For catalyst, the first step is occurred using pyridine and diethylamine catalysis
Knoevenagel reacts, and second step is catalyzed with piperidines occurs acetal ketone reaction, and after the completion of first step reaction, piperidines catalysis is added
Second step reacts, and the pyridine and diethylamine being added before this, which will not react second step, generates harmful effect, and the opposite first step is urged
Agent can also be catalyzed second step reaction, to make second step reaction more smoothly carry out.In conclusion cumarin base chalcone
Synthesis can be used be not added with separation continuous operation method, be conducive to improve yield.
The present invention synthesizes the serial cumarin base chalcone compounds of unification by one kettle way cascade reaction, yield with point
Step reaction yield (i.e. comparative example 1) comparison is shown in Table 1.
As shown in Table 1：During synthesizing coumarin base chalcone compounds, 6 target compound one kettle way productions
Rate is above the gross production rate of stepwise reaction, and 4.0%, 6.4%, 2.5%, 5.4%, 4.4% and has been respectively increased in yield
6.3%, to illustrate to effectively raise synthesizing coumarin base chalcone compounds using two step cascade reaction of one kettle way
Yield has important application value.Analyze reason, it should be to generate perfume carrying out aldol condensation in one pot reaction course
The reaction of formation for promoting 3- acetyl butylcoumariiis while legumin base chalcone again promotes 3- acetyl butylcoumariii and virtue later
Fragrant aldehyde continues aldol condensation and generates cumarin base chalcone；Simultaneously as the comprehensive catalysis of diethylamine, pyridine and piperidines,
Also it can further improve reaction yield.
1 stepwise reaction of table is compared with one pot reaction yield
Conclusion：It is found through experiments that one pot reaction yield will be apparently higher than stepwise reaction, meanwhile, one kettle way cascade reaction
Intermediate be not required to be separated, next step reaction can be carried out and eliminate purifying intermediate products to simplify operating procedure,
Be conducive to improve working efficiency, save the time, decrease the dosage of solvent, is conducive to environmental protection and reduces cost.
Claims (4)
1. the method for one pot process cumarin base chalcone compounds, which is characterized in that building-up process is as follows：
Salicylide is added into reaction bulb and ethyl acetoacetate sequentially adds diethylamine and pyridine under the conditions of 0-5 DEG C,
Ethyl alcohol, R-CHO and piperidines are sequentially added after stirring 10 ~ 30min at 10 DEG C of ＜, is heated to reflux to the reaction was complete, is cooled to room temperature,
Solvent is evaporated off, silica gel column chromatography separation obtains target compound, wherein salicylide, acetoacetate
The molar ratio of ethyl ester and R-CHO are 1 ︰（1~1.2）︰（1~1.2）, R is aryl.
2. the method for one pot process cumarin base chalcone compounds according to claim 1, which is characterized in that water
The molar ratio of poplar aldehyde, ethyl acetoacetate and R-CHO is 1 ︰, 1 ︰ 1.1.
3. the method for one pot process cumarin base chalcone compounds according to claim 2, which is characterized in that anti-
The dosage of each material is in answering：Salicylide 10mmol, ethyl acetoacetate 10mmol, diethylamine 0.05mL, pyridine 0.05mL, second
Alcohol 20mL, aromatic aldehyde 11mmol, piperidines 0.3mL, meanwhile, R is、、、、Or。
4. the method for one pot process cumarin base chalcone compounds according to claim 1, which is characterized in that silicon
When plastic column chromatography detaches, using the mixture of petroleum ether and ethyl acetate that volume ratio is 4 ︰, 1 to 8 ︰ 1 as eluant, eluent.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109293616A (en) * | 2018-09-29 | 2019-02-01 | 贵州大学 | One kind chalcones containing cumarin derivative, preparation method and application |
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| CN101275037A (en) * | 2008-04-08 | 2008-10-01 | 淮海工学院 | Coumarin type hemicyanine dye and preparation thereof |
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| CN101275037A (en) * | 2008-04-08 | 2008-10-01 | 淮海工学院 | Coumarin type hemicyanine dye and preparation thereof |
| CN104974744A (en) * | 2014-04-08 | 2015-10-14 | 深圳市汉康科技有限公司 | Thioredoxin reductase fluorescent probe, and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293616A (en) * | 2018-09-29 | 2019-02-01 | 贵州大学 | One kind chalcones containing cumarin derivative, preparation method and application |
| CN109293616B (en) * | 2018-09-29 | 2022-06-21 | 贵州大学 | Coumarin-containing chalcone derivatives, and preparation method and application thereof |
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