CN110467568A - A kind of synthetic method of aryl quinoline derivatives - Google Patents
A kind of synthetic method of aryl quinoline derivatives Download PDFInfo
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- CN110467568A CN110467568A CN201910774287.6A CN201910774287A CN110467568A CN 110467568 A CN110467568 A CN 110467568A CN 201910774287 A CN201910774287 A CN 201910774287A CN 110467568 A CN110467568 A CN 110467568A
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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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the 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
- C07D215/12—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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to technical field of organic synthesis, specially a kind of synthetic method of aryl quinoline derivatives.The present invention realizes the aryl quinoline derivatives synthesis of structure diversification by the continuous carbon-to-carbon of palladium chtalyst/carbon-nitrogen bond building.Specifically under palladium catalytic system, using compound (E) -3- (2- anilino-) acrylonitrile and aryl boric acid as raw material, 2- aryl quinoline derivatives are prepared.The method of the present invention raw material sources are extensive or easily prepared, easy to operate, selective controllable, high income, mild condition, and universality is wide.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to continuous carbon-to-carbon/carbon-nitrogen bond building is to realize knot
The diversified aryl quinoline derivatives synthetic method of structure.
Background technique
Chinoline backbone is widely present among bioactive molecule, is most representative heterocyclic compound in medicine and pesticide
One of object, and it is also played an important role in field of functional materials.In the existing technology for preparing quinoline, traditional technology is main
Using under the action of acid, alkali and suitable coupling reagent, synthesized by the condensation reaction of aniline, as Knorr,
Friedlander, Skraup reaction etc..These methods are inconvenient, equipment cost is required it is high, and the substrate scope of application compared with
It is narrow.Document (J.Org.Chem.2012,48,690-693 and Heterocyclic Chem.2016,53,1022-1029) report
Using arylamine and alcohol as raw material, at 150 DEG C, with CCl4For solvent, FeCl3·6H2O or Ni (OAc)2·4H2O is as catalysis
The method that aryl quinoline compound is prepared in coupling reaction occurs for agent.This method needs higher temperature, needs using toxic
CCl4As solvent, not only yield is not high, but also does not meet the needs of green chemistry.Document
(Org.Biomol.Chem.2017,15,1334) palladium chtalyst 2- vinyl benzene amine derivative and dimethyl sulfoxide cyclisation are reported
Although the method that reaction prepares aryl quinoline derivatives, this method do not need lengthy and tedious additive, but reaction temperature and condition
Harshness can just be gone on smoothly under the nitrogen atmosphere that 130 DEG C are spent, and atom utilization is not high, raw material is rare.These examples are all said
It is bright, easy to operate, relatively mild quinoline synthetic method be very it is necessary to.
Summary of the invention
In order to solve the problems existing in the prior art and insufficient, the object of the present invention is to provide a kind of aryl quinoline derivatives
Synthetic method, this method are raw material, highly selective, high receipts using (E) -3- (2- anilino-) acrylonitrile and aryl boric acid that are easy to get
It synthesizes to rate in 2- aryl quinoline derivatives.
To achieve the above object, the technical solution of the present invention is to provide synthesis 2- aryl quinoline derivatives method, packet
Include following steps:
Under palladium catalyst catalysis in a solvent, derivative with compound (E) -3- shown in formula (I) (2- anilino-) acrylonitrile
Object is raw material with compound aryl boric acid shown in formula (II), constructs reaction by continuous carbon-nitrogen bond, formula (III) institute is prepared
Show compound aryl quinoline derivatives；Its reaction equation are as follows:
In above-mentioned formula, R is hydrogen, methyl, methoxyl group, halogen, trifluoromethyl；
Ar is phenyl, thiophene；
The palladium catalyst can be palladium chloride PdCl2, acid chloride Pd (OAc)2, palladium trifluoroacetate Pd (TFA)2, four
(triphenylphosphine) palladium Pd (PPh3)4, palladium acetylacetonate Pd (acac)2, two (triphenylphosphine) palladium chloride Pd (PPh3)2Cl2In
Any one；
The solvent is toluene or dimethylbenzene or tetrahydrofuran；
The additive is p-methyl benzenesulfonic acid monohydrate or camphorsulfonic acid；
Compound shown in preparation formula (III), is calculated with molar ratio: formula (I) compound/formula (II) compound/palladium catalyst is
1.0/2.0/0.05。
Compound shown in preparation formula (III), reaction temperature are 90 DEG C.
Compound shown in preparation formula (III), reaction time 36h.
The present inventor has found a kind of under palladium catalytic system, aryl boric acid and (E) -3- (2- benzene by deeply and carefully studying
Amido) acrylonitrile can efficiently synthesize desired aryl quinoline very much, and Atom economy is high, and bonding is high-efficient, reaction condition
It is relatively mild.Compared to previous methods, reaction condition and substrate universality have clear improvement, and the present invention has the following advantages that and creates
New place:
(1) raw material (formula (I) compound and formula (II) compound) is from a wealth of sources, is easy to commercially available or preparation；
(2) the 2- phenylchinoline of a variety of substitute modes can be prepared, the substrate scope of application is greatly improved compared to document before；
(3) this is the important supplement of palladium chtalyst intercalation reaction, provides important thinking for building nitrogen-containing heterocycle compound；
(4) reaction condition is more mild.Compared to other catalyst systems, reacting required temperature be decreased significantly；
(5) reaction yield is high, and most of reaction yield is easy to later period separation 80% or more；
(6) reaction carries out under air atmosphere, is not necessarily to inert gas shielding, easy to operate.
The present invention compared with prior art the utility model has the advantages that
Aryl quinoline derivatives quality height is prepared using the method for the present invention, yield is higher；Raw material (formula (1) compound
With formula (II) compound) it is from a wealth of sources, universality is good, reaction of atomic economy is high, convenient post-treatment；It realizes for the first time more warm
The addition cyclization of transition metal-catalyzed aryl boric acid and (E) -3- (2- anilino-) acrylonitrile under the conditions of is aryl quinoline
Building with other heterocyclic compounds provides important reference.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with embodiment to the present invention make into
One step it is described in detail.
Embodiment 1
The preparation of 2- phenylchinoline, structural formula are as follows:
Under air atmosphere, be added raw material (E) -3- (2- aminobenzene) acrylonitrile (0.3mmol), phenyl boric acid (0.6mmol) and
Catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL), 90 DEG C of reaction 36h,
Product separation yield 90%.1H NMR(500MHz,CDCl3) δ 8.24-8.17 (m, 4H), 7.89 (d, J=11.0Hz, 1H),
7.84 (d, J=10.0Hz, 1H), 7.76-7.72 (m, 1H), 7.56-7.52 (m, 3H), 7.49-7.46 (m, 1H)；13C NMR
(125MHz,CDCl3)δ157.4,148.3,139.6,136.8,129.7,129.6,129.4,128.8,127.6,127.4,
127.2,126.3,119.0.
Embodiment 2
The preparation of 2- (4- aminomethyl phenyl) quinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- anilino-) acrylonitrile (0.3mmol), 4- methylphenylboronic acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 88%.1H NMR(500MHz,CDCl3)δ8.19-8.07(m,4H),7.87-7.81
(m,2H),7.72-7.71(m,1H),7.51-7.48(m,1H),7.34-7.33(m,2H),2.43(s,3H)；13C NMR
(125MHz,CDCl3)δ157.3,148.2,139.5,136.8,136.7,129.7,129.6,129.5,127.4,127.1,
126.1,118.9,21.3.
Embodiment 3
The preparation of 2- (3,5- 3,5-dimethylphenyl) quinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- anilino-) acrylonitrile (0.3mmol) is added, p-methyl benzenesulfonic acid one is hydrated
Object (0.6mmol), 3,5- dimethylphenyl boronic acids (0.6mmol) and catalyst palladium trifluoroacetate (5mol%), toluene (2mL), 90
DEG C reaction 36h, product separation yield 88%.1H NMR(500MHz,CDCl3) δ 8.20 (t, J=7.5Hz, 2H), 7.86 (d, J=
8.5Hz, 1H), 7.82 (d, J=8.5Hz, 1H), 7.78 (s, 2H), 7.75-7.72 (m, 1H), 7.52 (t, J=7.5Hz, 1H),
7.12(s,1H),2.45(s,6H)；13C NMR(125MHz,CDCl3)δ157.8,148.3,139.7,138.4,136.6,
131.1,129.7,129.6,127.5,127.2,126.2,125.5,119.3,21.5.
Embodiment 4
The preparation of 2- (1- naphthalene) quinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- anilino-) acrylonitrile (0.3mmol), 1- naphthalene phenyl boric acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 85%.1H NMR(500MHz,CDCl3) δ 8.28 (d, J=8.5Hz, 2H), 8.16 (d, J
=8.5Hz, 1H), 7.96 (t, J=8.5Hz, 2H), 7.91 (d, J=8.0Hz, 1H), 7.81-7.78 (m, 1H), 7.75 (d, J
=7.0Hz, 1H), 7.71 (d, J=8.5Hz, 1H), 7.63-7.59 (m, 2H), 7.55-7.47 (m, 2H)；13C NMR
(125MHz,CDCl3)δ159.4,148.1,138.7,136.3,134.1,131.3,129.8,129.7,129.2,128.4,
127.8,127.6,127.0,126.6,126.5,126.0,125.7,125.4,123.3.
Embodiment 5
The preparation of 2- (4- chlorphenyl) quinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- anilino-) acrylonitrile (0.3mmol), 4- chlorophenylboronic acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 80%.1H NMR(500MHz,CDCl3) δ 8.25-8.18 (m, 2H), 8.13 (d, J=
7.5Hz, 2H), 7.85-7.84 (m, 2H), 7.76-7.73 (m, 1H), 7.56-7.53 (m, 1H), 7.50 (d, J=7.5Hz,
2H)；13C NMR(125MHz,CDCl3)δ156.0,148.1,137.9,137.1,135.7,129.9,129.6,129.0,
128.9,127.5,127.2,126.6,118.6.
Embodiment 6
The preparation of 2- (3- thienyl) quinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- anilino-) acrylonitrile (0.3mmol), 3 methyl thiophene phenyl boric acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 75%.1H NMR(500MHz,CDCl3) δ 8.17 (d, J=9.0Hz, 2H), 8.10 (d, J
=11.0Hz, 2H), 7.82 (d, J=11.0Hz, 1H), 7.57-7.52 (m, 4H), 7.47 (t, J=9.0Hz, 1H), 2.55 (s,
3H)；13C NMR(125MHz,CDCl3)δ156.5,146.8,139.8,136.2,136.1,132.0,129.4,129.2,
128.8,127.5,127.2,126.3,119.0,21.6.
Embodiment 7
The preparation of 6- methyl -2- phenylchinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- amino -5- aminomethyl phenyl) acrylonitrile (0.3mmol), phenyl boric acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 95%.1H NMR(500MHz,CDCl3) δ 8.17 (d, J=9.0Hz, 2H), 8.10 (d, J
=11.0Hz, 2H), 7.82 (d, J=11.0Hz, 1H), 7.57-7.52 (m, 4H), 7.47 (t, J=9.0Hz, 1H), 2.55 (s,
3H)；13C NMR(125MHz,CDCl3)δ156.5,146.8,139.8,136.2,136.1,132.0,129.4,129.2,
128.8,127.5,127.2,126.3,119.0,21.6.
Embodiment 8
The preparation of the chloro- 2- phenylchinoline of 6-, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- amino -5- chlorphenyl) acrylonitrile (0.3mmol), phenyl boric acid is added
(0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL),
90 DEG C of reaction 36h, product separation yield 88%.1H NMR(CDCl3, 500MHz, ppm): δ 8.17 (d, J=8.0Hz, 2H),
7.79 (d, J=7.5Hz, 1H), 7.71 (d, J=7.5Hz, 1H), 7.40 (t, J=7.5Hz, 1H), 7.30 (t, J=7.5Hz,
1H), 7.20 (d, J=8.0Hz, 2H), 6.61 (s, 1H), 3.99 (s, 4H), 2.38 (s, 3H), 2.07 (s, 4H)13C NMR
(CDCl3,125MHz,ppm):δ163.7,147.7,145.1,136.4,135.0,132.0,130.5,129.2,128.3,
126.7,122.2,119.8,112.7,49.3,48.6,26.4,24.7,21.5.
Embodiment 9
The preparation of 4- methyl -2- phenylchinoline, structural formula are as follows:
Under air atmosphere, raw material (E) -3- (2- aminobenzene) -2- butene nitrile (0.3mmol), phenyl boric acid (0.6mmol) is added
With catalyst palladium trifluoroacetate (5mol%), p-methyl benzenesulfonic acid monohydrate (0.6mmol), toluene (2mL), 90 DEG C of reactions
36h, product separation yield 92%.1H NMR(500MHz,CDCl3) δ 8.22 (d, J=10.5Hz, 1H), 8.19-8.17 (m,
2H), 7.97 (d, J=10.5Hz, 1H), 7.73 (t, J=8.5Hz, 1H), 7.54 (t, J=8.5Hz, 1H), 7.49-7.46 (m,
1H),2.73(s,3H)；13C NMR(125MHz,CDCl3)δ157.0,148.2,144.8,139.8,130.3,129.3,
129.2,128.8,127.6,127.3,126.0,123.6,119.7,19.0.
The above disclosure is only the preferred embodiments of the present invention, cannot limit the right model of the present invention with this certainly
It encloses, therefore equivalent changes made in accordance with the claims of the present invention, is still within the scope of the present invention.
Claims (4)
1. a kind of synthetic method of aryl quinoline derivatives, characterized by comprising:
Palladium catalyst catalysis under in a solvent, with compound (E) -3- shown in formula (I) (2- anilino-) acrylic nitrile derivates with
Compound aryl boric acid shown in formula (II) is raw material, constructs reaction by continuous carbon-to-carbon/carbon-nitrogen bond, formula (III) is prepared
Shown compound aryl quinoline derivatives；Its reaction equation are as follows:
In above-mentioned formula, R is hydrogen, methyl, methoxyl group, halogen or trifluoromethyl；
Ar is phenyl or thiophene；
It is palladium chloride, acid chloride, palladium trifluoroacetate, tetrakis triphenylphosphine palladium, acetyl that the palladium catalyst, which is selected from palladium catalyst,
Any one in acetone palladium, two (triphenylphosphine) palladium chlorides；
The solvent is toluene or dimethylbenzene or tetrahydrofuran.
2. a kind of synthetic method of aryl quinoline derivatives according to claim 1, it is characterised in that: with molar ratio computing
Calculate: formula (I) compound/formula (II) compound/palladium catalyst is 1.0/2.0/0.05.
3. a kind of synthetic method of aryl quinoline derivatives according to claim 1, it is characterised in that: the reaction equation
Reaction temperature is 90 DEG C, reaction time 36h.
4. a kind of synthetic method of aryl quinoline derivatives according to claim 1, it is characterised in that: in the reaction
It further include that following additive is added, which is p-methyl benzenesulfonic acid monohydrate or camphorsulfonic acid.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111960987A (en) * | 2020-08-11 | 2020-11-20 | 温州大学 | Synthesis method of methylene bis (isoindole) compound |
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| CN103224436A (en) * | 2013-05-03 | 2013-07-31 | 温州大学 | Preparation method of o-amino diaryl ketone compound |
| CN104557701A (en) * | 2014-12-11 | 2015-04-29 | 温州大学 | Preparation method of isoquinoline derivative |
| CN104803912A (en) * | 2015-05-04 | 2015-07-29 | 刘增峰 | Synthetic method of medical intermediate quinoline compound |
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2019
- 2019-08-21 CN CN201910774287.6A patent/CN110467568A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103224436A (en) * | 2013-05-03 | 2013-07-31 | 温州大学 | Preparation method of o-amino diaryl ketone compound |
| CN104557701A (en) * | 2014-12-11 | 2015-04-29 | 温州大学 | Preparation method of isoquinoline derivative |
| CN104803912A (en) * | 2015-05-04 | 2015-07-29 | 刘增峰 | Synthetic method of medical intermediate quinoline compound |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111960987A (en) * | 2020-08-11 | 2020-11-20 | 温州大学 | Synthesis method of methylene bis (isoindole) compound |
| CN111960987B (en) * | 2020-08-11 | 2022-02-11 | 温州大学 | Synthesis method of methylene bis (isoindole) compound |
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Application publication date: 20191119 |