CN110156675A - The synthetic method of quinolines containing sulfonyl - Google Patents
The synthetic method of quinolines containing sulfonyl Download PDFInfo
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- CN110156675A CN110156675A CN201910560700.9A CN201910560700A CN110156675A CN 110156675 A CN110156675 A CN 110156675A CN 201910560700 A CN201910560700 A CN 201910560700A CN 110156675 A CN110156675 A CN 110156675A
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- quinolines
- synthetic method
- reaction
- containing sulfonyl
- sulfonyl
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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
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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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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention proposes a kind of synthetic method of quinolines containing sulfonyl; belong to organic synthesis field; reaction only can be completed without using metallic catalyst in the synthetic method under visible light catalyst effect, and reaction system is simple, reaction is high without heating, reaction yield.The technical solution includes that quinolines and sulfonic acid chloride class compound are separately added into reactor, under photochemical catalyst and solvent acetone effect, is reacted at room temperature 4-12 hours under white led lamps illumination condition；After reaction, pillar layer separation is carried out, the quinolines containing sulfonyl are obtained.Synthetic method provided by the present invention provides optimal substitution solution to efficiently synthesize the quinolines containing sulfonyl.
Description
Technical field
The invention belongs to organic synthesis field more particularly to a kind of synthetic methods of the quinolines containing sulfonyl.
Background technique
Quinolines containing sulfonyl have multiple biological activities, have obtained satisfied many-sided effect in recent years,
And the attention increasingly by whole world chemical research person.Currently, the existing workable quinolines containing sulfonyl
Preparation method be that quinolines and benzene sulfonic acid sodium salt react system in the presence of iodine catalyst, oxidant under hot conditions
It is standby to obtain (Chem.Commun., 2015,51,652).
However, in above-mentioned preparation process, catalyst is not used only in reaction system, but also need to be heated at high temperature and cause ring
Border is unfriendly, and products therefrom yield is also unsatisfactory etc..Therefore at present provided by method and uneconomical, be not containing sulphonyl yet
Optimal solution in the quinolines experiment synthesis of base.
Summary of the invention
The present invention proposes a kind of synthetic method of quinolines containing sulfonyl, and the synthetic method is without using metal
Reaction only can be completed in catalyst under visible light catalyst effect, and reaction system is simple, reaction is not necessarily to heating, reaction yield
Height provides optimal substitution solution to efficiently synthesize the quinolines containing sulfonyl.
In order to achieve the above object, the present invention provides a kind of synthetic method of quinolines containing sulfonyl,
It is characterized in that, includes the following steps:
It is separately added into quinolines and sulfonic acid chloride class compound into reactor, makees in photochemical catalyst and solvent acetone
Under, reacted at room temperature 4-12 hours under white led lamps illumination condition；
After reaction, pillar layer separation is carried out, the quinolines containing sulfonyl are obtained.
Preferably, the quinolines have following (A) structural formula:
Wherein, R1Selected from-CH3, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br.
Preferably, the sulfonic acid chloride class compound is in benzene sulfonyl chloride, p-methyl benzene sulfonic chloride or methylsufonyl chloride
Any one.
Preferably, the quinolines containing sulfonyl have following (B) structural formula:
Wherein, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br, R3It is any in-H, phenyl, tolyl
It is a kind of.
Preferably, a mM ratio for the quinolines and sulfonic acid chloride class compound is 1:(1-1.1).
Preferably, the photoinitiator is benzophenone.
Preferably, a mM ratio for the benzophenone and quinolines that are added is 0.1:1.
Preferably, chromatographic column used in the pillar layer separation is silicagel column, the eluant, eluent used is ethyl acetate
With the mixed solvent of petroleum ether, volume ratio 1:5-2:1.
Compared with prior art, the advantages and positive effects of the present invention are:
Synthetic method provided by the present invention is being not necessarily to using quinolines and sulfonic acid chloride class compound as base stock
In the case where metal residues, reaction can be completed using only visible light catalyst.The synthetic method reaction system is simple, reacts nothing
It needs to heat, room temperature condition, LED lamplight can be operated under the conditions of shining, and reaction products therefrom yield is high, contain sulfonyl to efficiently synthesize
Quinolines provide optimal substitution solution.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects
It encloses.
The embodiment of the invention provides a kind of synthetic methods of quinolines, include the following steps:
S1: quinolines and sulfonic acid chloride class compound are separately added into reactor, in photochemical catalyst and solvent third
Under ketolysis, reacted at room temperature 4-12 hours under white led lamps illumination condition；
In this step, the quinolines chemical combination containing sulfonyl is synthesized using quinolines and sulfonic acid chloride class compound
Object becomes oxygen radical specifically, benzophenone is excited under illumination condition, then captures the benzyl position of quinolines
Hydrogen atom, generate carbon radicals, in next step with sulfonic acid chloride react generate target product.What needs to be explained here is that the step
Reaction is reacted, it is seen that the dosage of the preferred benzophenone of photochemical catalyst is extremely low, and the reaction time under room temperature without heating
It is short；In addition, this method is selectively good, products collection efficiency may be up to 97%.In a preferred embodiment, used LED light is 8W
's.It is understood that the reaction time set in the step according to set by reaction temperature, intensity of light, ability
Field technique personnel can adjust the reaction time according to actually required, as long as ensuring to react abundant.
S2: after reaction, pillar layer separation is carried out, the quinolines containing sulfonyl are obtained.
In a preferred embodiment, the quinolines have following (A) structural formula:
Wherein, R1Selected from-CH3, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br.
In a preferred embodiment, the sulfonic acid chloride class compound is benzene sulfonyl chloride, p-methyl benzene sulfonic chloride or methyl sulphur
Any one in acyl chlorides.
In a preferred embodiment, the quinolines containing sulfonyl have following (B) structural formula:
Wherein, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br, R3It is any in-H, phenyl, tolyl
It is a kind of.
The concrete structure formula of quinolines containing sulfonyl used in specifically defining in above-described embodiment, can be with
Understand, the quinolines containing sulfonyl defined in the present embodiment are using quinoline as parent nucleus, by its gained compound
In branched structure it is relatively simple, but be not precluded in the present embodiment be made of the more complicated branched structure of structure containing sulphonyl
The quinolines of base.
In a preferred embodiment, a mM ratio for the quinolines and sulfonic acid chloride class compound is 1:(1-
1.1).In a preferred embodiment, a mM ratio for the benzophenone and quinolines that are added is 0.1:1.
In the above-described embodiments, the specific ratio of quinolines, sulfonic acid chloride class compound and benzophenone is given,
Wherein, in order to accurately obtaining the mother nucleus structure of expecting compound, the ratio of quinolines and sulfonic acid chloride class compound
Based on reaction mechanism requirement, catalyst amount is extremely low for setting, and the additional amount of solvent is then relatively can be excessive, to ensure sufficiently
Reaction.
In a preferred embodiment, chromatographic column used in the pillar layer separation is silicagel column, and the eluant, eluent used is
The mixed solvent of ethyl acetate and petroleum ether, volume ratio 1:5-2:1.In the present embodiment, reaction products therefrom is utilized
Silicagel column carries out gradient elution, thus isolated expected synthetic product.According to the similar principle and in view of synthetic product of mixing
Polarity size, select in the present embodiment the mixed solvent for the ethyl acetate and petroleum ether that volume ratio is 1:5-2:1 to carry out gradient
Elution, in the range, those skilled in the art can be adjusted according to the actual situation.
In order to become apparent from the synthesis for introducing the quinolines provided by the embodiment of the present invention containing sulfonyl in detail
Method is described below in conjunction with specific embodiment.
Embodiment 1
It is separately added into reactor1mmol, benzene sulfonyl chloride 1mmol, benzophenone 0.1mmol, acetone
2ml, Yu Baise 8W LED lamplight react at room temperature 4 hours under the conditions of shining, and carry out pillar layer separation after reaction, obtain targeted
Close object C1:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows:
1H NMR (500MHz, CDCl3) δ 8.06 (d, J=8.4Hz, 1H), 7.75 (d, J=8.5Hz, 1H), 7.71 (d, J
=8.1Hz, 1H), 7.62-7.53 (m, 3H), 7.46 (t, J=9.8Hz, 3H), 7.30 (t, J=7.8Hz, 2H), 4.67 (s,
2H)；
13C NMR(126MHz,CDCl3)δ149.25s,147.80,138.30,136.97,133.82,129.93,
129.11,128.97,128.52,127.61,127.36,127.21,122.76,65.14；
After identified, spectral data is corresponding with structural formula, it was demonstrated that and synthesis is 2- ((phenyl sulfonyl) methyl) quinoline,
Yield 97%.
Embodiment 2
It is separately added into reactor1mmol, benzene sulfonyl chloride 1.1mmol, benzophenone
0.1mmol, acetone 2ml, Yu Baise 8W LED lamplight react at room temperature 6 hours under the conditions of shining, and carry out column chromatography point after reaction
From obtaining target compound C2:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows:
1H NMR(500MHz,CDCl3) δ 8.04 (d, J=8.4Hz, 1H), 7.73 (s, 1H), 7.65 (d, J=8.7Hz,
1H), 7.59 (d, J=7.9Hz, 2H), 7.49 (dd, J=15.2,7.9Hz, 2H), 7.39 (d, J=8.7Hz, 1H), 7.34 (t,
J=7.6Hz, 2H), 4.63 (s, 2H)；
13C NMR(126MHz,CDCl3)δ150.44,148.13,138.20,136.72,135.76,133.96,
129.05,128.85,128.47,128.26,128.18,125.68,122.96,65.12；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 7- chloro- 2- (phenyl sulfonyl) methyl)
Quinoline, yield 92%.
Embodiment 3
It is separately added into reactor1mmol, benzene sulfonyl chloride 1.1mmol, benzophenone 0.1mmol,
Acetone 2ml, Yu Baise 8W LED lamplight reacts at room temperature 12 hours under the conditions of shining, and carries out pillar layer separation after reaction, obtains
Target compound C3:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned yellow solid powder, data are as follows:
1H NMR(500MHz,CDCl3) δ 8.08 (d, J=8.4Hz, 1H), 7.74 (d, J=8.6Hz, 1H), 7.68 (d, J
=7.7Hz, 2H), 7.64-7.48 (m, 4H), 7.42 (t, J=7.5Hz, 2H), 4.74 (s, 2H), 2.54 (s, 3H)
13C NMR(126MHz,CDCl3)δ148.21,146.47,138.26,137.22,136.23,133.77,
132.22,128.93,128.82,128.55,127.41,126.40,122.73,65.20,21.63；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 6- methyl -2- ((phenyl sulfonyl) first
Base) quinoline, yield 91%.
Embodiment 4
It is separately added into reactor1mmol, p-methyl benzene sulfonic chloride 1mmol, benzophenone
0.1mmol, acetone 2ml, Yu Baise 8W LED lamplight react at room temperature 4 hours under the conditions of shining, and carry out column chromatography point after reaction
From obtaining target compound C4:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows:
1H NMR (500MHz, CDCl3) δ 8.16 (d, J=8.3Hz, 1H), 7.88 (d, J=8.5Hz, 1H), 7.82 (d, J
=8.1Hz, 1H), 7.68 (t, J=7.6Hz, 1H), 7.56 (t, J=9.5Hz, 4H), 7.21 (d, J=7.7Hz, 2H), 4.73
(s,2H),2.39(s,3H)；
13C NMR(126MHz,CDCl3)δ149.40,147.87,144.83,136.87,135.46,129.85,
129.62,129.20,128.52,127.61,127.37,127.14,122.75,65.32,21.63；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 2- (tosylmethyl) quinoline, is produced
Rate 95%.
Embodiment 5
It is separately added into reactor1mmol, p-methyl benzene sulfonic chloride 1mmol, benzophenone
0.1mmol, acetone 2ml, Yu Baise 8W LED lamplight react at room temperature 4 hours under the conditions of shining, and carry out column chromatography point after reaction
From obtaining target compound C5:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows:
1H NMR(500MHz,CDCl3) δ 8.10 (d, J=8.4Hz, 1H), 7.98-7.79 (m, 1H), 7.65-7.51 (m,
3H), 7.44 (t, J=9.8Hz, 2H), 7.21 (d, J=7.7Hz, 2H), 4.70 (s, 2H), 2.39 (s, 3H)；
13C NMR(126MHz,CDCl3) δ 161.70,159.71,148.80 (d, J=2.8Hz), 144.95 (d, J=
12.9Hz), 136.18 (d, J=5.5Hz), 135.44,131.80 (d, J=9.2Hz), 129.64,128.50,128.06 (d, J
=10.1Hz), 123.48,120.26,120.05,110.70,110.53,65.17,21.63；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 6- fluoro- 2- (tosylmethyl) quinoline
Quinoline, yield 96%.
Embodiment 6
It is separately added into reactorP-methyl benzene sulfonic chloride 1mmol, hexichol first
Ketone 0.1mmol, acetone 2ml, Yu Baise 8W LED lamplight react at room temperature 5 hours under the conditions of shining, and carry out column chromatography after reaction
Separation, obtains target compound C6:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned yellow solid powder, data are as follows:
1H NMR(500MHz,CDCl3) δ 8.06 (d, J=8.4Hz, 1H), 7.96 (s, 1H), 7.73 (s, 2H), 7.57
(dd, J=16.5,8.1Hz, 3H), 7.21 (d, J=7.7Hz, 2H), 4.70 (s, 2H), 2.39 (s, 3H)；
13C NMR(126MHz,CDCl3)δ149.92,146.39,144.94,135.81,135.36,133.33,
130.92,129.66,129.63,128.48,128.40,123.62,121.10,65.22,21.65；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 6- bromo- 2- (tosylmethyl) quinoline
Quinoline, yield 96%.
Embodiment 7
It is separately added into reactor1mmol, methylsufonyl chloride 1mmol, benzophenone
0.1mmol, acetone 2ml, Yu Baise 8W LED lamplight react at room temperature 5 hours under the conditions of shining, and carry out column chromatography point after reaction
From obtaining target compound C7:
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows:
1H NMR (500MHz, DMSO) δ 8.48 (d, J=8.4Hz, 1H), 8.15-8.00 (m, 2H), 7.69 (d, J=
8.6Hz,2H),4.89(s,2H),3.13(s,3H)；
13C NMR(126MHz,DMSO)δ152.70,148.03,137.57,135.06,130.45,128.14,127.83,
126.15,124.36,62.39,41.23；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is the chloro- 2- of 7- ((mesyl) methyl) quinoline
Quinoline, yield 93%.
Claims (8)
1. the synthetic method of the quinolines containing sulfonyl, which comprises the steps of:
It is separately added into quinolines and sulfonic acid chloride class compound into reactor, is acted in photochemical catalyst and solvent acetone
Under, it is reacted at room temperature 4-12 hours under white led lamps illumination condition；
After reaction, pillar layer separation is carried out, the quinolines containing sulfonyl are obtained.
2. synthetic method according to claim 1, which is characterized in that the quinolines have following (A) structure
Formula:
Wherein, R1Selected from-CH3, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br.
3. synthetic method according to claim 1, which is characterized in that the sulfonic acid chloride class compound is benzene sulfonyl chloride, right
Any one in toluene sulfonyl chloride or methylsufonyl chloride.
4. synthetic method according to claim 1, which is characterized in that the quinolines containing sulfonyl have such as
Under (B) structural formula:
Wherein, R2Selected from-H ,-Cl ,-CH3,-F, any one in-Br, R3It is any one in-H, phenyl, tolyl
Kind.
5. synthetic method according to claim 1, which is characterized in that the quinolines and sulfonic acid chloride class compound
MM than be 1:(1-1.1).
6. synthetic method according to claim 1, which is characterized in that the photochemical catalyst is benzophenone.
7. synthetic method according to claim 6, which is characterized in that the benzophenone that is added and quinolines
MM than be 0.1:1.
8. synthetic method according to claim 1, which is characterized in that chromatographic column used in the pillar layer separation is silicon
Rubber column gel column, the eluant, eluent used are the mixed solvent of ethyl acetate and petroleum ether, volume ratio 1:5-2:1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117304160A (en) * | 2023-11-23 | 2023-12-29 | 山东华夏神舟新材料有限公司 | Synthesis method of perfluoro-2, 2-dimethyl-4, 5-tetrachloro-1, 3-dioxolane |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530354A (en) * | 2018-05-07 | 2018-09-14 | 青岛农业大学 | A kind of synthetic method of the compound of class containing phenylsulfonylquinoline |
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2019
- 2019-06-26 CN CN201910560700.9A patent/CN110156675B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530354A (en) * | 2018-05-07 | 2018-09-14 | 青岛农业大学 | A kind of synthetic method of the compound of class containing phenylsulfonylquinoline |
Non-Patent Citations (2)
| Title |
|---|
| L. HAZAI, ET AL.: ""PREFERRED CARBON VS. NITROGEN SULFONYLATION ON β-CARBOLINES"", 《SYNTHETIC COMMUNICATIONS》 * |
| XIAO, FUHONG , ET AL.,: ""Efficient 2-sulfolmethyl quinoline formation from 2-methylquinolines and sodium sulfinates under transition-metal free conditions"", 《CHEMICAL COMMUNICATIONS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117304160A (en) * | 2023-11-23 | 2023-12-29 | 山东华夏神舟新材料有限公司 | Synthesis method of perfluoro-2, 2-dimethyl-4, 5-tetrachloro-1, 3-dioxolane |
| CN117304160B (en) * | 2023-11-23 | 2024-03-15 | 山东华夏神舟新材料有限公司 | Synthesis method of perfluoro-2, 2-dimethyl-4, 5-tetrachloro-1, 3-dioxolane |
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