CN108299291A - It is acylated the synthetic method of quinoline or isoquinilone derivatives - Google Patents
It is acylated the synthetic method of quinoline or isoquinilone derivatives Download PDFInfo
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- CN108299291A CN108299291A CN201810097717.0A CN201810097717A CN108299291A CN 108299291 A CN108299291 A CN 108299291A CN 201810097717 A CN201810097717 A CN 201810097717A CN 108299291 A CN108299291 A CN 108299291A
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- MDWCIKACMBMJFA-UHFFFAOYSA-N O=C(c1ccccc1)c1nccc2ccccc12 Chemical compound O=C(c1ccccc1)c1nccc2ccccc12 MDWCIKACMBMJFA-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
It is acylated the synthetic method of quinoline or isoquinilone derivatives, the invention belongs to organic synthesis fields, it is poor in order to solve the problems, such as to react complicated, condition harshness, the feature of environmental protection present in existing quinoline or isoquinilone derivatives synthetic method.Synthetic method：Under nitrogen atmosphere; using quinoline or isoquinolin and benzoyl formic acid as reaction raw materials; using persulfate as oxidant; using metal iridium compound as visible light catalyst; it is added in reaction vessel, is reacted under visible light illumination condition, after the completion of reaction together with organic solvent; reaction system obtains being acylated quinoline or isoquinilone derivatives by filtering, concentrating and isolate and purify.The present invention is placed in progress illumination under visible light source under nitrogen atmosphere, by reaction system to react, and entire reaction process safety and environmental protection, reaction condition is simple, and operating procedure is convenient, belongs to green chemistry process.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of synthetic method being acylated (different) quinoline derivatives.
Background technology
(different) quinoline derivatives are a kind of common and important nitrogen heterocyclic, (different) quinoline containing different functional groups
Quinoline class compound can show a variety of different bioactivity and pharmacological activity, such as antibacterial, antiviral, anti-malarial and antitumor
Deng, at present medicine and pesticide field be widely applied.(different) quinoline derivatives can be directly from various natural products
In directly extract, the Papaverine (papaverine) as shown in following structural formula is exactly to be extracted from opium poppy, it contains different
Chinoline backbone structure has analgesic effect.In addition, this analog derivative can also be obtained by using chemically synthesized method,
The Neratinib as shown in following structural formula is a kind of small point containing chinoline backbone structure researched and developed by Wyeth companies of the U.S.
Sub- tyrosine kinase inhibitor has been used for the clinical research for treating breast cancer and advanced solid tumor etc..Other than pharmacological action,
(different) quinoline derivatives can be also used for the fields such as dyestuff, antioxidant, food feed additive and various chemical assistants.
Research accordingly, with respect to various (different) quinoline derivatives of effectively composite structure receives close pass in organic synthesis field
Note.
Currently, there are many method report about synthesis (different) quinoline derivatives, but still there is shortcomings.Example
Such as, traditional synthetic method is usually required using acidic materials such as concentrated hydrochloric acid or the concentrated sulfuric acids, and this provides for improved in industrial production
Equipment requirement, while also increasing environmental pressure.It is severe that there is also reaction conditions in some novel method for synthesizing developed in recent years
The problems such as quarter or reaction step are cumbersome.Therefore, seek a kind of environmentally protective, simple and fast and efficient (different) quinoline derivatives
Synthetic method have important research meaning.
Invention content
The invention aims to solve to react complicated, item present in existing quinoline or isoquinilone derivatives synthetic method
Part harshness, the problem of feature of environmental protection difference, and the novel method for synthesizing for being acylated quinoline or isoquinilone derivatives is provided.
The present invention is acylated quinoline or the synthetic method of isoquinilone derivatives is realized according to the following steps：
Under nitrogen atmosphere, using quinoline or isoquinolin and benzoyl formic acid as reaction raw materials, using persulfate as oxygen
Agent is added in reaction vessel, in visible light illumination together using metal iridium compound as visible light catalyst with organic solvent
Under the conditions of reacted, after the completion of reaction, reaction system by filtering, concentrate and isolate and purify, obtain be acylated quinoline or different
Quinoline, wherein the visible light catalyst is [Ir (ppy)2(dtbbpy)](PF6) or 4CzIPN.
The reaction formula of the synthesizing acylated quinoline of the present invention is as follows：
Wherein substituent R1Represent H or Cl, R2Represent H, Cl or Me.
The reaction formula of the synthesizing acylated isoquinilone derivatives of the present invention is as follows：
Wherein substituent R1Represent H or Cl, R2Represent H, Cl or Me.
The present invention is placed in progress illumination under visible light source under nitrogen atmosphere, by reaction system to react, charging sequence
Arbitrarily, simple to operate.The reaction raw materials that the present invention uses need not move through complicated synthesis, and raw material can be directly commercially available,
The oxidant persulfate of use is cheap and pollution-free.And the reaction substrate of the present invention is applied widely, can utilize anti-
The change of substituent R in substrate is answered to bring the synthesis for realizing different substituted acylation (different) quinolines.The present invention is entirely anti-
Answer process safety environmentally friendly, reaction condition is simple, and operating procedure is convenient, belongs to green chemistry process.
Description of the drawings
Fig. 1 is that embodiment three synthesizes obtained 3- methyl-1s-benzoyl isoquinolin1H NMR spectras；
Fig. 2 is that embodiment three synthesizes obtained 3- methyl-1s-benzoyl isoquinolin13C NMR spectras.
Specific implementation mode
Specific implementation mode one：Present embodiment is acylated quinoline or the synthetic method of isoquinilone derivatives presses following step
It is rapid to implement：
Under nitrogen atmosphere, using quinoline or isoquinolin and benzoyl formic acid as reaction raw materials, using persulfate as oxygen
Agent is added in reaction vessel, in visible light illumination together using metal iridium compound as visible light catalyst with organic solvent
Under the conditions of reacted, after the completion of reaction, reaction system by filtering, concentrate and isolate and purify, obtain be acylated quinoline or different
Quinoline, wherein the visible light catalyst is [Ir (ppy)2(dtbbpy)](PF6) or 4CzIPN.
The structural formula of present embodiment quinoline is：The structural formula of isoquinolin is：
Wherein substituent R1Represent H or Cl, R2Represent H, Cl or Me.
The reaction raw materials that present embodiment uses can be directly commercially available, and the oxidant of use is cheap and to environment
It is pollution-free.Present embodiment will be seen that photocatalyst applications in the synthetic reaction of quinoline or isoquinilone derivatives for the first time, and
Photochemical catalyst dosage used in reaction is few, and can also recycle after completion of the reaction.
Specific implementation mode two：The present embodiment is different from the first embodiment in that the persulfate is over cure
Sour ammonium, potassium peroxydisulfate or sodium peroxydisulfate.Other steps and parameter are same as the specific embodiment one.
Specific implementation mode three：The present embodiment is different from the first and the second embodiment in that quinoline or isoquinolin with
The molar ratio of benzoyl formic acid is 1:2.Other steps and parameter are the same as one or two specific embodiments.
Specific implementation mode four：The persulfuric acid unlike one of present embodiment and specific implementation mode one to three
Salt is 2 with the molar ratio of quinoline or isoquinolin:1.Other steps and parameter are identical as one of specific implementation mode one to three.
Specific implementation mode five：The metal iridium unlike one of present embodiment and specific implementation mode one to four
The addition of compound is the 3%~6% of the amount of quinoline or isoquinolin substance.Other steps and parameter and specific implementation mode
One of one to four is identical.
Specific implementation mode six：Present embodiment metal iridium compound described unlike specific implementation mode five
Addition is the 5% of the amount of quinoline or isoquinolin substance.Other steps and parameter are identical as specific implementation mode five.
Specific implementation mode seven：It is described organic molten unlike one of present embodiment and specific implementation mode one to six
Agent is dimethyl sulfoxide (DMSO) (DMSO), dichloromethane, acetonitrile, dichloroethanes, tetrahydrofuran or N,N-dimethylformamide.Other steps
Rapid and parameter is identical as one of specific implementation mode one to six.
Specific implementation mode eight：Present embodiment every mM of quinoline or isoquinoline unlike specific implementation mode seven
Quinoline uses 5~10 milliliters of organic solvent.Other steps and parameter are identical as specific implementation mode seven.
Specific implementation mode nine：In visible light illumination unlike one of present embodiment and specific implementation mode one to eight
Under the conditions of carry out 10~16h of reaction.Other steps and parameter are identical as one of specific implementation mode one to eight.
Specific implementation mode ten：With petroleum ether/second unlike one of present embodiment and specific implementation mode one to nine
The mixed solution of acetoacetic ester carries out silica gel column chromatography separating purification as eluant, eluent.Other steps and parameter and specific embodiment party
One of formula one to nine is identical.
Embodiment one：The synthetic method that the present embodiment is acylated isoquinilone derivatives is implemented according to the following steps：
26mg isoquinolin, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8And 11mg
Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process, reaction vessel closing is added with syringe
And the deoxygenation inflated with nitrogen under -78 DEG C of low temperature, reaction vessel is placed under blue LED lamp and carries out illumination reaction in room temperature condition
Water is added into reaction system and is extracted with dichloromethane, merges organic phase by 12h, after processing is dried with anhydrous sodium sulfate,
It filters and is concentrated to give crude product after rotating solvent, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel
Column chromatography purifies and separates obtain 1- benzoyl isoquinolin.
The structural formula for the 1- benzoyl isoquinolin that the present embodiment obtains is：
The yield of the 1- benzoyl isoquinolin of the present embodiment synthesis is 81%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.60 (d, J=5.5Hz, 1H), 8.21 (d, J=8.5Hz, 1H), 7.96 (d, J=7.6Hz, 2H),
7.91 (d, J=8.4Hz, 1H), 7.80 (d, J=5.5Hz, 1H), 7.73 (t, J=7.5Hz, 1H), 7.60 (t, J=7.9Hz,
2H), 7.47 (t, J=7.5Hz, 2H)13C NMR(151MHz,CDCl3)δ194.84,156.48,141.22,136.75,
136.66,133.78,130.82,128.55,128.41,127.18,126.47,126.21,122.70。
Embodiment two：The synthetic method that the present embodiment is acylated isoquinilone derivatives is implemented according to the following steps：
33mg 5- chlorine isoquinolin, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process, reaction vessel is added with syringe
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, to reaction system by closing and at low temperature deoxygenation inflated with nitrogen
Middle addition water is simultaneously extracted with dichloromethane, merges organic phase, after processing is dried with anhydrous sodium sulfate, is filtered and is concentrated to give thick
Product, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel column chromatography purifies and separates, it is chloro- to obtain 5-
1- benzoyl isoquinolin.
The structural formula for the chloro- 1- benzoyls isoquinolin of 5- that the present embodiment obtains is：
The yield of the chloro- 1- benzoyls isoquinolin of 5- of the present embodiment synthesis is 81%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.71 (d, J=5.9Hz, 1H), 8.22 (d, J=5.9Hz, 1H), 8.14 (d, J=8.5Hz, 1H),
7.96-7.89 (m, 2H), 7.82 (dd, J=7.5,0.7Hz, 1H), 7.62 (t, J=7.4Hz, 1H), 7.56-7.50 (m, 1H),
7.48 (t, J=7.7Hz, 2H)13C NMR(151MHz,CDCl3)δ194.44,156.85,142.43,136.43,134.66,
134.02,131.67,130.85,130.79,128.66,128.26,127.38,125.33,118.99。
Embodiment three：The synthetic method that the present embodiment is acylated isoquinilone derivatives is implemented according to the following steps：
29mg 3- methylisoquinoliniums, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8
With 11mg Ir [dF (CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process is added with syringe, reaction is held
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, to reactant by device closing and at low temperature deoxygenation inflated with nitrogen
Water is added in system and is extracted with dichloromethane, merges organic phase, after processing is dried with anhydrous sodium sulfate, filters and be concentrated to give
Crude product, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel column chromatography purifies and separates, obtain 3-
Methyl-1-benzoyl isoquinolin.
The structural formula for 3- methyl-1s-benzoyl isoquinolin that the present embodiment obtains is：
3- methyl-1s-benzoyl isoquinolin yield of the present embodiment synthesis is 68%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.06 (d, J=8.5Hz, 1H), 7.96 (d, J=7.6Hz, 2H), 7.80 (d, J=8.3Hz, 1H),
7.65 (s, 1H), 7.60 (d, J=9.7Hz, 2H), 7.46 (dd, J=14.4,7.2Hz, 3H), 2.72 (s, 3H)13C NMR
(151MHz,CDCl3)δ195.03,156.37,150.35,137.42,136.50,133.81,130.93,130.67,
128.52,127.28,126.58,126.02,124.47,120.54,24.23。
Example IV：The synthetic method that the present embodiment is acylated quinoline is implemented according to the following steps：
26mg quinoline, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8With 11mg Ir
[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process is added with syringe, reaction vessel is closed simultaneously
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, is added into reaction system by deoxygenation inflated with nitrogen at low temperature
Water is simultaneously extracted with dichloromethane, is merged organic phase, after processing is dried with anhydrous sodium sulfate, is filtered and be concentrated to give crude product,
Again using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, silica gel column chromatography purifies and separates are carried out, 2- benzoyls are obtained
Quinoline.
The structural formula for the 2- benzoyl quinoline that the present embodiment obtains is：
The yield of the 2- benzoyl quinoline of the present embodiment synthesis is 30%, and nuclear magnetic data is：1H NMR(400MHz,
CDCl3) δ 8.35 (d, J=8.5Hz, 1H), 8.22 (dd, J=13.8,8.2Hz, 3H), 8.11 (d, J=8.4Hz, 1H), 7.91
(d, J=8.1Hz, 1H), 7.79 (t, J=7.6Hz, 1H), 7.72-7.58 (m, 2H), 7.52 (t, J=7.5Hz, 2H)13C
NMR(151MHz,CDCl3)δ193.99,154.83,146.87,137.27,136.26,133.23,131.60,130.69,
130.25,129.05,128.57,128.31,127.80,120.96。
Embodiment five：The synthetic method that the present embodiment is acylated quinoline is implemented according to the following steps：
33mg 4- chloroquinolines, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process, reaction vessel is added with syringe
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, to reaction system by closing and at low temperature deoxygenation inflated with nitrogen
Middle addition water is simultaneously extracted with dichloromethane, merges organic phase, after processing is dried with anhydrous sodium sulfate, is filtered and is concentrated to give thick
Product, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel column chromatography purifies and separates, it is chloro- to obtain 4-
2- benzoyl quinoline.
The structural formula for the chloro- 2- benzoyls quinoline of 4- that the present embodiment obtains is：
The yield of the chloro- 2- benzoyls quinoline of 4- of the present embodiment synthesis is 63%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.31 (dd, J=8.4,1.0Hz, 1H), 8.23 (dd, J=9.7,8.3Hz, 4H), 7.84 (ddd, J=
8.4,7.0,1.4Hz, 1H), 7.76 (ddd, J=8.2,7.0,1.2Hz, 1H), 7.68-7.61 (m, 1H), 7.52 (dd, J=
10.6,4.7Hz,2H).13C NMR(151MHz,CDCl3)δ192.66,154.46,147.65,143.94,135.83,
133.43,131.56,131.07,131.03,129.60,128.34,127.20,124.25,121.10。
Embodiment six：The synthetic method that the present embodiment is acylated quinoline is implemented according to the following steps：
29mg 4- methylquinolines, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process, reaction vessel is added with syringe
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, to reaction system by closing and at low temperature deoxygenation inflated with nitrogen
Middle addition water is simultaneously extracted with dichloromethane, merges organic phase, after processing is dried with anhydrous sodium sulfate, is filtered and is concentrated to give thick
Product, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel column chromatography purifies and separates, obtain 4- first
Base -2- benzoyl quinoline.
The structural formula for the 4- methyl -2- benzoyl quinoline that the present embodiment obtains is：
The yield of the 4- methyl -2- benzoyl quinoline of the present embodiment synthesis is 76%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.28-8.15 (m, 1H), 8.08 (d, J=7.9Hz, 1H), 7.94 (s, 1H), 7.83-7.73 (m,
1H), 7.73-7.65 (m, 1H), 7.62 (t, J=7.4Hz, 1H), 7.51 (t, J=7.6Hz, 1H), 2.81 (s, 1H)13C NMR
(151MHz,CDCl3)δ194.33,154.52,146.72,145.78,136.32,133.18,131.59,131.27,
129.86,129.08,128.30,128.27,123.90,121.43,19.08。
Embodiment seven：The synthetic method that the present embodiment is acylated quinoline is implemented according to the following steps：
29mg 2- methylquinolines, 60mg benzoyl formic acids, 91mg (NH are separately added into 5mL round-bottomed flasks4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvents of the 2mL through drying process, reaction vessel is added with syringe
Reaction vessel is placed in progress illumination reaction 12h under blue LED lamp, to reaction system by closing and at low temperature deoxygenation inflated with nitrogen
Middle addition water is simultaneously extracted with dichloromethane, merges organic phase, after processing is dried with anhydrous sodium sulfate, is filtered and is concentrated to give thick
Product, then using the mixed solution of petrol ether/ethyl acetate as eluant, eluent, carry out silica gel column chromatography purifies and separates, obtain 2- first
Base -4- benzoyl quinoline.
The structural formula for the 2- methyl -4- benzoyl quinoline that the present embodiment obtains is：
The yield of the 2- methyl -4- benzoyl quinoline of the present embodiment synthesis is 56%, and nuclear magnetic data is：1H NMR
(400MHz,CDCl3) δ 8.11 (d, J=8.5Hz, 1H), 7.85 (d, J=7.6Hz, 2H), 7.78 (d, J=8.3Hz, 1H),
7.72 (t, J=7.6Hz, 1H), 7.64 (t, J=7.4Hz, 1H), 7.47 (dd, J=16.7,8.3Hz, 3H), 7.29 (s, 1H),
2.79(s,3H).13C NMR(151MHz,CDCl3)δ196.39,158.30,148.28,144.78,136.68,134.20,
130.31,130.05,129.20,128.81,126.72,125.20,123.30,120.42,25.46。
By embodiment one to embodiment seven it is found that the present invention carries out illumination under nitrogen atmosphere to react, charging sequence
Arbitrarily, simple to operate.The reaction raw materials that the present invention uses need not move through complicated synthesis, and raw material is commercially available, the oxygen of use
Agent persulfate is cheap and easily-available and pollution-free, and the present invention can utilize the change of substituent group in (different) quinoline substrate to bring reality
The synthesis of existing different substituted acyl (different) quinolines.The entire reaction process safety and environmental protection of the present invention, it is easy to operate, belong to
Green chemistry process.
Claims (10)
1. being acylated the synthetic method of quinoline or isoquinilone derivatives, it is characterised in that this method is realized according to the following steps：
Under nitrogen atmosphere, using quinoline or isoquinolin and benzoyl formic acid as reaction raw materials, using persulfate as oxidant,
Using metal iridium compound as visible light catalyst, it is added in reaction vessel together with organic solvent, in visible light illumination condition
Under reacted, after the completion of reaction, reaction system by filtering, concentrate and isolate and purify, obtain being acylated quinoline or isoquinolin
Derivative, wherein the visible light catalyst is [Ir (ppy)2(dtbbpy)](PF6) or 4CzIPN.
2. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
Persulfate is ammonium persulfate, potassium peroxydisulfate or sodium peroxydisulfate.
3. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that quinoline or
The molar ratio of person's isoquinolin and benzoyl formic acid is 1:2.
4. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
Persulfate is 2 with the molar ratio of quinoline or isoquinolin:1.
5. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
The addition of metal iridium compound is the 3%~6% of the amount of quinoline or isoquinolin substance.
6. the synthetic method according to claim 5 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
The addition of metal iridium compound is the 5% of the amount of quinoline or isoquinolin substance.
7. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
Organic solvent is dimethyl sulfoxide (DMSO), dichloromethane, acetonitrile, dichloroethanes, tetrahydrofuran or N,N-dimethylformamide.
8. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that per mmoles
That quinoline or isoquinolin use 5~10 milliliters of organic solvent.
9. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that visible
10~16h of reaction is carried out under light illumination condition.
10. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that with oil
The mixed solution of ether/ethyl acetate carries out silica gel column chromatography separating purification as eluant, eluent.
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| CN109776406A (en) * | 2019-03-09 | 2019-05-21 | 湘潭大学 | A kind of method of ether compound and quinoline derivatives cross-coupling |
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| CN104163768A (en) * | 2013-05-17 | 2014-11-26 | 中国科学院理化技术研究所 | Method for preparing aniline derivative by catalyzing acyl migration with visible light |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109776406A (en) * | 2019-03-09 | 2019-05-21 | 湘潭大学 | A kind of method of ether compound and quinoline derivatives cross-coupling |
| CN109776406B (en) * | 2019-03-09 | 2021-05-04 | 湘潭大学 | Method for cross coupling of ether compound and quinoline derivative |
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