CN117820222A - Method for synthesizing 3-arylquinoline-2 (1H) -ketone derivative by carbonylation - Google Patents
Method for synthesizing 3-arylquinoline-2 (1H) -ketone derivative by carbonylation Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 19
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 16
- 230000006315 carbonylation Effects 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims abstract description 18
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 claims abstract description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 12
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 6
- 239000011733 molybdenum Substances 0.000 claims abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- -1 methoxy, methoxycarbonyl Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000012039 electrophile Substances 0.000 abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- 238000001514 detection method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 238000010499 C–H functionalization reaction Methods 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- YTFJQDNGSQJFNA-UHFFFAOYSA-N benzyl dihydrogen phosphate Chemical class OP(O)(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing 3-arylquinoline-2 (1H) -ketone derivatives by carbonylation, which comprises the following steps: palladium acetate, 2-dicyclohexylphosphine-2 ',4',6' -triisopropyl biphenyl, molybdenum carbonyl, potassium carbonate, water, benzisoxazole and a benzylsulfonyl chloride compound are reacted at 110 ℃ for 26 hours, and after the reaction is completed, the 3-arylquinoline-2 (1H) -ketone derivative is obtained after post treatment. The method uses benzisoxazole as a nitrogen source and a formyl source, uses benzyl sulfonyl chloride compound as a C (sp 3) electrophile, and has the advantages of simple operation, cheap and easily obtained reaction initial raw materials, wide tolerance range of substrate functional groups and high reaction efficiency. Can synthesize various 3-aryl quinoline-2 (1H) -ketone derivatives according to actual needs, is convenient to operate and widens the practicability of the method.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing a 3-arylquinoline-2 (1H) -ketone derivative by carbonylation.
Background
3-arylquinolin-2 (1H) -one derivatives are an attractive class of azaheterocyclic compounds that are widely found in natural products, bioactive molecules and drugs (J.Med. Chem.1992,35, 3423-3425). They have very remarkable biological activities such as anti-tumor, anti-platelet, anti-high pressure, etc. In addition, 3-arylquinolin-2 (1H) -one derivatives are often used as important intermediates and have very important applications in organic synthesis (J.Org.chem.2005, 70, 2555-2567). The synthesis of 3-arylquinolin-2 (1H) -one derivatives has also attracted considerable attention from chemists due to their widespread use in natural products, drug discovery and material science. Conventional synthesis methods mainly include Vilsmeier Haack, knorr and Friedlander reactions, and other synthesis methods such as transition metal catalyzed reactions and ring closure metathesis reactions have also been developed. Despite certain advances in the synthetic methods of such compounds, development of a direct and efficient method for synthesizing 3-arylquinolin-2 (1H) -one derivatives remains worthy of further investigation.
Palladium catalyzed carbonylation is a highly efficient, economical, direct process that has wide application in the synthesis of carbonyl-containing compounds and is also receiving increasing attention from both academia and industry. The carbonylation reaction typically uses aryl halides as the primary electrophiles, however, the use of C (sp 3) electrophiles remains a significant challenge compared to the C (sp 2) electrophiles described above. Although a variety of C (sp 3) electrophiles have been developed, such as benzyl halides, benzyl acetate/carbonates, benzyl phosphates, benzyl ammonium salts, and benzylamines, the development of new C (sp 3) electrophiles in carbonylation reactions is still highly desirable. Sulfonyl chlorides, one of the most commonly used reagents in organic synthesis, have recently been used as a very effective class of electrophiles in C-C bond coupling and C-H bond functionalization reactions. Such reagents can remove SO under the catalysis of transition metals 2 Subsequent cross-coupling reactions thus occur to yield the corresponding product. Therefore, the development of carbonylation reactions with sulfonyl chloride as electrophile has good development prospects.
Based on this, we developed a palladium catalyzed carbonylation reaction for the synthesis of 3-arylquinolin-2 (1H) -one derivatives. The reaction starts from a simple and easily available benzisoxazole and a benzylsulfonyl chloride compound, uses the benzisoxazole as a nitrogen source and a formyl source, uses benzyl sulfonyl chloride as a C (sp 3) electrophile, synthesizes a plurality of 3-arylquinolin-2 (1H) -one derivatives, and opens up a new way for the reaction of synthesizing the 3-arylquinolin-2 (1H) -one derivatives by carbonylation.
Disclosure of Invention
The invention provides a method for synthesizing 3-aryl quinoline-2 (1H) -ketone derivatives by carbonylation, which has the advantages of simple steps, low-cost and easily available reaction raw materials, compatibility with various functional groups, good reaction applicability, and novel direction for synthesizing 3-aryl quinoline-2 (1H) -ketone derivatives by carbonylation by taking benzyl sulfonyl chloride compound as a C (sp 3) electrophile.
A method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation, comprising the steps of: reacting a palladium catalyst, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, molybdenum carbonyl, potassium carbonate, water, benzisoxazole and a benzylsulfonyl chloride compound at 90-110 ℃ for 24-28 hours, and after the reaction is completed, performing post-treatment to obtain the 3-arylquinoline-2 (1H) -ketone derivative;
the structure of the benzisoxazole is shown as a formula (II):
the structure of the benzylsulfonyl chloride compound is shown as a formula (III):
the structure of the 3-arylquinolin-2 (1H) -one derivative is shown in formula (I):
in the formulae (I) to (III), R 1 H, C of a shape of H, C 1 ～C 4 Alkoxy, C 1 ～C 4 Alkoxycarbonyl or halogen; r is R 2 H, C of a shape of H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxycarbonyl, trifluoromethoxy or halogen;
the molar ratio of the palladium catalyst to the 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl to the potassium carbonate to the water is 0.1:0.2:5:1;
R 1 ，R 2 the substitution positions of (c) may be para, ortho or meta.
The reaction formula is as follows:
in the invention, the optional post-treatment process comprises: filtering, mixing with silica gel, and purifying by column chromatography to obtain corresponding 3-arylquinolin-2 (1H) -one derivative, wherein column chromatography is used as a common technical means in the art.
Preferably, R 1 In this case, the benzisoxazole is easily obtained and the reaction yield is high.
Preferably, R 2 In the case of H, methyl, tert-butyl, trifluoromethoxy, methoxycarbonyl, F, cl or Br, the benzylsulfonyl chloride compound is readily available and the reaction yield is high.
The benzisoxazole and benzylsulfonyl chloride compounds described for the carbonylation of 3-arylquinolin-2 (1H) -one derivatives are relatively inexpensive and widely available in nature, preferably in molar amounts: benzylsulfonyl chloride compound: palladium catalyst=1:2.5-3:0.05-0.1; as a further preference, benzisoxazole is used in molar terms: benzylsulfonyl chloride compound: palladium catalyst=1:2.5:0.1.
Preferably, the reaction time is 26 hours, and the reaction time is too long to increase the reaction cost, but on the contrary, it is difficult to ensure the completion of the reaction.
Preferably, the reaction is carried out in acetonitrile in an amount to provide good dissolution of the starting materials, with 0.1mmol of benzisoxazole using an amount of acetonitrile of about 1 to 3mL.
Preferably, the palladium catalyst is palladium acetate, and among a plurality of palladium catalysts, palladium acetate is relatively inexpensive, and the reaction efficiency is relatively high when palladium acetate is used as the catalyst.
As a further preferred aspect, the 3-arylquinolin-2 (1H) -one derivative is one of the compounds of formula (I-1) -formula (I-5):
the compounds represented by the formulae (I-1) to (I-5) are known compounds.
In the above method, the benzisoxazole, the benzylsulfonyl chloride compound, the molybdenum carbonyl, the palladium acetate, the 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl and the potassium carbonate are generally commercially available products, and can be conveniently obtained from the market.
Compared with the prior art, the invention has the beneficial effects that: the method has the advantages of simplicity, easy operation, simple and convenient post-treatment, low-cost and easily-obtained reaction initial raw materials, wide tolerance range of substrate functional groups and high reaction efficiency by taking benzisoxazole as a nitrogen source and a formyl source and benzyl sulfonyl chloride compound as a C (sp 3) electrophile. Can synthesize various 3-aryl quinoline-2 (1H) -ketone derivatives according to actual needs, and has strong practicability.
Detailed Description
The invention is further described below in connection with specific embodiments.
Examples 1 to 15
Palladium acetate, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, molybdenum carbonyl, potassium carbonate, water, benzisoxazole (II) and a benzylsulfonyl chloride compound (III) are added into a 15mL sealed tube according to the raw material ratio of Table 1, acetonitrile (1 mL) is then added, the mixture is uniformly mixed and stirred, the reaction is carried out according to the reaction conditions of Table 2, after the reaction is completed, the mixture is filtered, silica gel is stirred, and the corresponding 3-arylquinoline-2 (1H) -ketone derivative (I) is obtained through column chromatography purification, wherein the reaction process is shown as the following formula:
TABLE 1 amounts of raw materials to be added in examples 1 to 15
TABLE 2
In tables 1 and 2, T is the reaction temperature, T is the reaction time, T-Bu is T-butyl, CO 2 Me is ester group, OMe is methoxy, me is methyl, OCF 3 Is trifluoromethoxy.
Structure confirmation data for the compounds prepared in examples 1 to 5:
nuclear magnetic resonance of 3-arylquinolin-2 (1H) -one derivative (I-1) prepared in example 1 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,DMSO-d 6 )δ11.95(s,1H),8.09(s,1H),7.77–7.71(m,3H),7.52–7.47(m,1H),7.45–7.41(m,2H),7.39–7.33(m,2H),7.21–7.17(m,1H).
13 C NMR(101MHz,DMSO-d 6 )δ161.1,138.4,137.7,136.3,131.6,130.2,128.7,128.1,128.0,127.8,121.9,119.6,114.7.
nuclear magnetic resonance of 3-arylquinolin-2 (1H) -one derivative (I-2) prepared in example 2 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,DMSO-d 6 )δ11.91(s,1H),8.06(s,1H),7.70(t,J＝8.6Hz,3H),7.51–7.43(m,3H),7.32(d,J＝8.2Hz,1H),7.19(t,J＝7.5Hz,1H),1.32(s,9H).
13 C NMR(101MHz,DMSO-d 6 )δ161.1,150.3,138.3,137.1,133.4,131.5,130.0,128.4,128.0,124.7,121.8,119.6,114.6,34.3,31.1.
nuclear magnetic resonance of 3-arylquinolin-2 (1H) -one derivative (I-3) prepared in example 3 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,DMSO-d 6 )δ12.04(s,1H),8.24(s,1H),8.01(d,J＝8.5Hz,2H),7.94(d,J＝8.5Hz,2H),7.77–7.75(m,1H),7.55–7.51(m,1H),7.36–7.34(m,1H),7.23–7.19(m,1H),3.88(s,3H).
13 C NMR(101MHz,DMSO-d 6 )δ166.1,160.8,141.0,138.8,138.6,130.8,130.2,128.9,128.8,128.7,128.4,122.1,119.4,114.8,52.2.
nuclear magnetic resonance of 3-arylquinolin-2 (1H) -one derivative (I-4) prepared in example 4 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,DMSO-d 6 )δ11.83(s,1H),8.05(s,1H),7.76–7.73(m,2H),7.45–7.41(m,2H),7.39–7.35(m,1H),7.29–7.26(m,2H),7.17–7.14(m,1H),3.79(s,3H).
13 C NMR(101MHz,DMSO-d 6 )δ160.6,154.2,137.2,136.4,132.9,131.9,128.7,127.9,127.8,120.1,119.4,116.0,109.4,55.4.
nuclear magnetic resonance of 3-arylquinolin-2 (1H) -one derivative (I-5) prepared in example 5 1 H NMR 13 C NMR) detection data were:
1 H NMR(400MHz,DMSO-d 6 )δ12.08(s,1H),8.09(s,1H),7.83(d,J＝2.4Hz,1H),7.75–7.72(m,2H),7.55–7.52(m,1H),7.46–7.42(m,2H),7.41–7.39(m,1H),7.35–7.33(m,1H).
13 C NMR(101MHz,DMSO-d 6 )δ160.8,137.1,136.5,135.9,132.8,130.0,128.7,128.1,128.0,127.0,125.6,120.7,116.6。
Claims (8)
1. a method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation, comprising the steps of: reacting a palladium catalyst, a ligand, molybdenum carbonyl, alkali, water, benzisoxazole and a benzylsulfonyl chloride compound for 24-28 hours at 90-110 ℃, and after the reaction is completed, carrying out post-treatment to obtain the 3-arylquinolin-2 (1H) -one derivative;
the structure of the benzisoxazole is shown as a formula (II):
the structure of the benzylsulfonyl chloride compound is shown as a formula (III):
the structure of the 3-arylquinolin-2 (1H) -one derivative is shown in formula (I):
in the formulae (I) to (III), R 1 H, C of a shape of H, C 1 ～C 4 Alkoxy, C 1 ～C 4 Alkoxycarbonyl or halogen; r is R 2 H, C of a shape of H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxycarbonyl, trifluoromethoxy or halogen.
2. The method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation according to claim 1, wherein R 1 Is H, methoxy, methoxycarbonyl, cl or Br; r is R 2 Is H, methyl, tertiary butyl, methoxycarbonyl, trifluoromethoxy, F, cl or Br.
3. The process for the oxo-synthesis of 3-arylquinolin-2 (1H) -one derivatives according to claim 1, wherein the benzisoxazole is calculated on a molar basis: benzylsulfonyl chloride compound: molybdenum carbonyl: palladium catalyst: ligand: alkali: water=1:2.5-3:3-3.5:0.05-0.1:0.1-0.2:4-6:1-2.
4. The method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation according to claim 1, wherein acetonitrile is used as a solvent.
5. The method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation according to claim 1, wherein the palladium catalyst is palladium acetate.
6. The method for synthesizing 3-arylquinolin-2 (1H) -one derivatives according to claim 1, wherein the ligand is 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl.
7. The method for synthesizing 3-arylquinolin-2 (1H) -one derivatives by carbonylation according to claim 1, wherein the base is potassium carbonate.
8. The method for synthesizing 3-arylquinolin-2 (1H) -one derivative according to claim 1, wherein the 3-arylquinolin-2 (1H) -one derivative is one of compounds represented by formula (I-1) -formula (I-5):
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