CN108299291B - 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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- 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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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 complicated reaction present in existing quinoline or isoquinilone derivatives synthetic method, condition harshness, the feature of environmental protection.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 reaction was completed together with organic solvent; reaction system obtains being acylated quinoline or isoquinilone derivatives by filtering, being concentrated and isolate and purify.Under nitrogen atmosphere, reaction system is placed in progress illumination under visible light source to react the present invention, 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 for being acylated (different) quinoline derivatives.
Background technique
(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 as shown in following structural formula (papaverine) is exactly to extract 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 by the research and development of Wyeth company, 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 (different) quinoline derivatives of effectively composite structure multiplicity 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.
Summary of the invention
The invention aims to solve reaction complexity, 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 reaction was completed, reaction system by filtering, be concentrated 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.
Under nitrogen atmosphere, reaction system is placed in progress illumination under visible light source to react the present invention, 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 reaction substrate of the invention is applied widely, can use anti-
The transformation of substituent R in substrate is answered to realize the synthesis of 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.
Detailed description of the invention
Fig. 1 is that embodiment three synthesizes obtained 3- methyl-1-benzoyl isoquinolin1H NMR spectra；
Fig. 2 is that embodiment three synthesizes obtained 3- methyl-1-benzoyl isoquinolin13C NMR spectra.
Specific embodiment
Specific embodiment 1: 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 reaction was completed, reaction system by filtering, be concentrated 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 are as follows:The structural formula of isoquinolin are as follows: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 for the first time photocatalyst applications in the synthetic reaction of quinoline or isoquinilone derivatives, and
Photochemical catalyst dosage used in reaction is few, and can also recycle after completion of the reaction.
Specific embodiment 2: 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 embodiment 3: 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 embodiment 4: persulfuric acid described unlike one of present embodiment and specific embodiment one to three
The molar ratio of salt and quinoline or isoquinolin is 2:1.Other steps and parameter are identical as one of specific embodiment one to three.
Specific embodiment 5: metal iridium described unlike one of present embodiment and specific embodiment one to four
The additional amount of compound is the 3%~6% of the amount of quinoline or isoquinolin substance.Other steps and parameter and specific embodiment
One of one to four is identical.
Specific embodiment 6: present embodiment metal iridium compound described unlike specific embodiment five
Additional amount is the 5% of the amount of quinoline or isoquinolin substance.Other steps and parameter are identical as specific embodiment five.
Specific embodiment 7: described organic molten unlike one of present embodiment and specific embodiment one to six
Agent is dimethyl sulfoxide (DMSO), methylene chloride, acetonitrile, dichloroethanes, tetrahydrofuran or N,N-dimethylformamide.Other steps
Rapid and parameter is identical as one of specific embodiment one to six.
Specific embodiment 8: present embodiment every mM of quinoline or isoquinoline unlike specific embodiment seven
Quinoline uses 5~10 milliliters of organic solvent.Other steps and parameter are identical as specific embodiment seven.
Specific embodiment 9: in visible light illumination unlike one of present embodiment and specific embodiment one to eight
Under the conditions of carry out 10~16h of reaction.Other steps and parameter are identical as one of specific embodiment one to eight.
Specific embodiment 10: with petroleum ether/second unlike one of present embodiment and specific embodiment 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 acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8And 11mg
Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried, 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 being 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
The separation of column chromatographic purifying, obtains 1- benzoyl isoquinolin.
The structural formula for the 1- benzoyl isoquinolin that the present embodiment obtains are as follows:
The yield of the 1- benzoyl isoquinolin of the present embodiment synthesis is 81%, nuclear magnetic data are as follows: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 acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried, 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, and merges organic phase, after being dried with anhydrous sodium sulfate, filters 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 of the chloro- 1- benzoyl isoquinolin of the 5- that the present embodiment obtains are as follows:
The yield of the chloro- 1- benzoyl isoquinolin of 5- of the present embodiment synthesis is 81%, nuclear magnetic data are as follows: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- methylisoquinolinium, 60mg benzoyl formic acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8
With 11mg Ir [dF (CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried 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 being 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.
3- methyl-1-benzoyl isoquinolin structural formula that the present embodiment obtains are as follows:
3- methyl-1-benzoyl isoquinolin yield of the present embodiment synthesis is 68%, nuclear magnetic data are as follows: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 acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8With 11mg Ir
[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried 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, and merges organic phase, after being dried with anhydrous sodium sulfate, filters 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- benzoyl is obtained
Quinoline.
The structural formula for the 2- benzoyl quinoline that the present embodiment obtains are as follows:
The yield of the 2- benzoyl quinoline of the present embodiment synthesis is 30%, nuclear magnetic data are as follows: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- chloroquinoline, 60mg benzoyl formic acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried, 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, and merges organic phase, after being dried with anhydrous sodium sulfate, filters 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 of the chloro- 2- benzoyl quinoline of the 4- that the present embodiment obtains are as follows:
The yield of the chloro- 2- benzoyl quinoline of 4- of the present embodiment synthesis is 63%, nuclear magnetic data are as follows: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- methylquinoline, 60mg benzoyl formic acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried, 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, and merges organic phase, after being dried with anhydrous sodium sulfate, filters 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 are as follows:
The yield of the 4- methyl -2- benzoyl quinoline of the present embodiment synthesis is 76%, nuclear magnetic data are as follows: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- methylquinoline, 60mg benzoyl formic acid, 91mg (NH are separately added into 5mL round-bottomed flask4)2S2O8With
11mg Ir[dF(CF3)ppy]2(dtbbpy)(PF6), DMSO solvent of the 2mL through being dried, 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, and merges organic phase, after being dried with anhydrous sodium sulfate, filters 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 are as follows:
The yield of the 2- methyl -4- benzoyl quinoline of the present embodiment synthesis is 56%, nuclear magnetic data are as follows: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 transformation of substituent group in (different) quinoline substrate to come in fact
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 (9)
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 reaction was completed, reaction system by filtering, be concentrated and isolate and purify, obtain being acylated quinoline or isoquinolin
Derivative, the structural formula that product is acylated quinoline are；Product is acylated isoquinilone derivatives
Structural formula is, wherein R1Represent H, R2Represent H；The visible light catalyst is [Ir (ppy)2
(dtbbpy)](PF6) or 4CzIPN；The molar ratio of raw material quinoline or isoquinolin and benzoyl formic acid is 1:2.
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 described
The molar ratio of persulfate and quinoline or isoquinolin is 2:1.
4. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
The additional amount of metal iridium compound is the 3%~6% of the amount of quinoline or isoquinolin substance.
5. the synthetic method according to claim 4 for being acylated quinoline or isoquinilone derivatives, it is characterised in that described
The additional amount of metal iridium compound is the 5% of the amount of quinoline or isoquinolin substance.
6. 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, methylene chloride, acetonitrile, dichloroethanes, tetrahydrofuran or N,N-dimethylformamide.
7. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that every mmoles
That quinoline or isoquinolin use 5 ~ 10 milliliters of organic solvent.
8. 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.
9. the synthetic method according to claim 1 for being acylated quinoline or isoquinilone derivatives, it is characterised in that with petroleum
Ether/ethyl acetate mixed solution carries out silica gel column chromatography separating purification as eluant, eluent.
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| Homolytic Acylation of Protonated Pyridines and Pyrazines with a-Keto Acids: The Problem of Monoacylation;Francesca Fontana et al.;《J. Org. Chem.》;19910618;第56卷;2866-2869 * |
| Silver catalyzed decarboxylative acylation of pyridine-N-oxides using a-oxocarboxylic acids;Rajendran Suresh et al.;《RSC Adv.》;20140708;第4卷;31685-31688 * |
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