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Synthesis method of 2-aryl quinoline compound

A synthesis method and arylquinoline technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, poor tolerance of substrate functional groups, and complicated operation.

Pending Publication Date: 2022-01-14
温州医科大学附属口腔医院
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Problems solved by technology

[0004] As can be seen above, although there are multiple preparation methods for preparing 2-arylquinoline compounds in the existing technology based on ring expansion reaction, most of these methods have complex operations, severe conditions, difficult raw material synthesis, and low yields. Low, poor tolerance of substrate functional groups and many other disadvantages

Method used

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  • Synthesis method of 2-aryl quinoline compound
  • Synthesis method of 2-aryl quinoline compound
  • Synthesis method of 2-aryl quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of 2-phenylquinoline

[0030]

[0031] In a dry and clean reactor, add 15mL solvent water and 5mL solvent tetrahydrofuran, then add the above formula (II) compound, formula (III) compound, palladium acetate, bipyridine, p-toluenesulfonic acid successively, so that the molar ratio is 1 : 2: 0.05: 0.1: 8, wherein the compound of formula (II) is 3 mmol. The reaction system was stirred and reacted at 80° C. for 24 hours. After the reaction, the solvent in the reactor was removed by a rotary evaporator, and the residue was purified by column chromatography with 200-300 mesh silica gel to obtain the target product as a yellow oil with a yield of 86%.

[0032] NMR data: 1 H NMR (500MHz, CDCl 3 )δ8.22-8.18(m, 4H), 7.87(d, J=8.5Hz, 1H), 7.83(d, J=8.0Hz, 1H), 7.76-7.73(m, 1H), 7.56-7.52(m , 3H), 7.50-7.47(m, 1H); 13 C NMR (125MHz, CDCl 3)δ157.3, 148.2, 139.6, 136.7, 129.7, 129.6, 129.3, 128.8, 127.5, 127.4, 127.1, 126.2, 118.9.

Embodiment 2

[0033] Embodiment 2: the synthesis of 2-(o-tolyl) quinoline

[0034]

[0035] In a dry and clean reactor, add 15mL solvent water and 5mL solvent tetrahydrofuran, then add the above formula (II) compound, formula (III) compound, palladium acetate, bipyridine, p-toluenesulfonic acid successively, so that the molar ratio is 1 : 2: 0.06: 0.12: 8, wherein the compound of formula (II) is 3 mmol. The reaction system was stirred and reacted at 90° C. for 24 hours. After the reaction, the solvent in the reactor was removed by a rotary evaporator, and the residue was purified by column chromatography with 200-300 mesh silica gel to obtain the target product as a yellow oil with a yield of 75%.

[0036] NMR data: 1 H NMR (500MHz, CDCl 3 )δ8.23-8.18 (m, 2H), 7.87 (d, J=8.5Hz, 1H), 7.77-7.74 (m, 1H), 7.59-7.54 (m, 2H), 7.53-7.51 (m, 1H) , 2.43(s, 3H); 13 C NMR (125MHz, CDCl 3 )δ160.2, 147.8, 140.6, 136.1, 136.0, 130.8, 129.7, 129.6, 129.5, 128.5, 127.5, 126.7, 126.4, 126.0, 122.3,...

Embodiment 3

[0037] Embodiment 3: the synthesis of 2-(p-tolyl) quinoline

[0038]

[0039] In a dry and clean reactor, add 15mL solvent water and 5mL solvent tetrahydrofuran, then add the above formula (II) compound, formula (III) compound, palladium acetate, bipyridine, p-toluenesulfonic acid successively, so that the molar ratio is 1 : 2: 0.05: 0.1: 10, wherein the compound of formula (II) is 3 mmol. The reaction system was stirred and reacted at 90° C. for 24 hours. After the reaction, the solvent in the reactor was removed by a rotary evaporator, and the residue was purified by column chromatography with 200-300 mesh silica gel to obtain the target product as a yellow oil with a yield of 88%.

[0040] NMR data: 1 H NMR (400MHz, CDCl 3 )δ8.19(d, J=8.4Hz, 2H), 8.08(d, J=8.4Hz, 2H), 7.86(d, J=8.4Hz, 1H), 7.83-7.80(m, 1H), 7.75- 7.71(m, 1H), 7.54-7.50(m, 1H), 7.35(d, J=8.0Hz, 2H), 2.45(s, 3H); 13 C NMR (125MHz, CDCl 3 )δ157.3, 148.2, 139.4, 136.7, 136.7, 129.6, 129.6, 129.5, 127.4...

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Abstract

The invention relates to a synthesis method of 2-aryl quinoline, wherein the synthesis method comprises the step: in the presence of a palladium source compound as a catalyst, carrying out addition ring-expansion reaction on a 2-(2-oxoindol-3-yl) acetonitrile compound and an arylboronic acid compound so as to prepare the 2-aryl quinoline compound. The method has the advantages of being simple in reaction, easy and convenient to operate, rich in raw material source, high in product yield, high in purity and the like, a brand new synthesis method is provided for preparation of the compound, and the method has good industrial prospects and potential application value.

Description

technical field [0001] The invention relates to a synthesis method of quinoline compounds, in particular to a synthesis method of 2-aryl quinoline compounds, belonging to the field of organic chemistry synthesis. Background technique [0002] Quinoline is an important class of biologically active molecules, which widely exist in various pharmaceutical and pesticide compounds. The Pfissinger reaction is a common method for the synthesis of quinolines. The Pfeissinger reaction is based on the ring expansion reaction, and the addition-ring expansion reaction of isatin and carbonyl compounds under basic conditions generates quinoline compounds. [0003] The synthesis of quinolines based on ring expansion reactions has been reported by many people, but the reaction substrates are all isatin or carbon-containing cycloalkanes. Literature (Org. Biomol. Chem., 2013, 11, 5254-5263; RSC Adv., 2014, 4, 36890-36895; Org. Lett. 2011, 13, 4782-4785; ACS Comb. Sci. 2014, 16, 333-341;) re...

Claims

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Application Information

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IPC IPC(8): C07D215/04C07D215/14C07D409/04C07D405/04
CPCC07D215/04C07D215/14C07D409/04C07D405/04
Inventor 胡晓冬
Owner 温州医科大学附属口腔医院
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