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Fluorinated isoquinoline compounds and preparation method thereof

A technology for isoquinolines and compounds, which is applied in the field of fluoroisoquinoline compounds and their preparation, can solve the problems of harsh conditions, cumbersome routes, and few methods for fluoroisoquinoline compounds, and achieve low cost and low substrate good compatibility

Inactive Publication Date: 2015-02-18
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, due to the fact that there are not many methods for synthesizing fluoroisoquinoline compounds at present, and there are many problems such as cumbersome routes, poor substrate compatibility, and harsh conditions, the number of fluoroisoquinoline compounds that can be screened for activity is limited. Limited, so that it hinders the application research of this type of compound in the fields of medicine and pesticide

Method used

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  • Fluorinated isoquinoline compounds and preparation method thereof
  • Fluorinated isoquinoline compounds and preparation method thereof
  • Fluorinated isoquinoline compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: preparation of

[0029] 3.4mg (0.02mmol) of AgNO 3 , 7.4mg (0.1mmol) of Li 2 CO 3 , 47.5mg (0.15mmol) of N-fluorobisbenzenesulfonamide (NFSI) was added to the reaction tube, 1.5mL of N,N-dimethylacetamide was added, and then 24.1mg (0.1mmol) of alkyne substrate was added Stir the reaction at 30°C for 5 hours; add water, extract with diethyl ether, combine the extracts, concentrate, column chromatography, and elute with ethyl acetate and petroleum ether gradient to obtain 17.7 mg of the product The yield was 87%.

[0030] 1 H NMR (400MHz, CDCl 3 ):9.07(s,1H),8.03(d,J=8.4Hz,1H),7.94(d,J=8.4Hz,1H),7.71(dd,J=7.2,7.2Hz,1H),7.57(dd ,J=7.2,7.2Hz,1H),3.00(dt,J=8.0,2.4Hz,2H),1.79(tt,J=8.0,7.6Hz,2H),1.43(tq,J=7.6,7.6Hz, 2H),0.96(q,J=7.6Hz,3H);

[0031] 13 C NMR (100MHz, CDCl 3 ): 152.2(d, J=255.7Hz), 147.2(d, J=6.1Hz), 140.7(d, J=16.0Hz), 130.3, 128.8(d, J=2.3Hz), 126.9, 126.8(d, J=2.3Hz), 126.5(d, J=16.7Hz), 119.3(d, J=4.5Hz), 31.2, 30.7, 22.5, 13.9;

...

Embodiment 2

[0034] Example 2: preparation of

[0035] 3.4mg (0.02mmol) of AgNO 3 , 7.4mg (0.1mmol) of Li 2 CO 3 , 47.5mg (0.15mmol) of N-fluorobisbenzenesulfonamide (NFSI) was added to the reaction tube, 1.5mL of N,N-dimethylacetamide was added, and then 26.1mg (0.1mmol) of alkyne substrate was added Stir the reaction at 30°C for 6 hours; add water, extract with ether, combine the extracts, concentrate, column chromatography, and elute with ethyl acetate and petroleum ether gradient to obtain 19.4 mg of the product The yield was 87%.

[0036] 1 H NMR (400MHz, CDCl 3 ):9.13(s,1H),8.12(d,J=8.4Hz,1H),8.10(d,J=8.4Hz,2H),7.97(d,J=8.4Hz,1H),7.73(dd,J =8.0,7.2Hz,1H),7.61(t,J=7.2Hz,1H),7.52(d,J=7.2Hz,2H),7.42(t,J=7.2Hz,1H);

[0037] 13 C NMR (100MHz, CDCl 3 ): 132.3(d, J=262.5Hz), 147.6(d, J=6.1Hz), 136.6(d, J=10.6Hz), 135.7(d, J=5.4Hz), 130.6(d, J=1.5Hz ),,129.4(d,J=2.3Hz),128.9(d,J=6.0Hz),128.5,128.4,127.8,127.3(d,J=16.7Hz),126.9(d,J=1.5Hz),119.9 (d, J=5.3Hz);

[0038] 19 F NMR...

Embodiment 3

[0040] Example 3: preparation of

[0041] 3.4mg (0.02mmol) of AgNO 3 , 7.4mg (0.1mmol) of Li 2 CO 3 , 95.0mg (0.15mmol) of N-fluorobisbenzenesulfonamide (NFSI) was added to the reaction tube, 1.5mL of N,N-dimethylacetamide was added, and then 22.5mg (0.1mmol) of alkyne substrate was added Stir the reaction at 60°C for 7 hours; add water, extract with ether, combine the extracts, concentrate, column chromatography, and elute with ethyl acetate and petroleum ether gradient to obtain 10.5 mg of the product The yield was 56%.

[0042] 1 H NMR (400MHz, CDCl 3 ):8.91(s,1H),8.00(d,J=8.4Hz,1H),7.90(d,J=8.0Hz,1H),7.70(dd,J=8.4,8.0Hz,1H),7.53(dd ,J=8.0,8.0Hz,1H),2.54-2.43(m,1H),1.22-1.15(m,2H),1.09-1.01(m,2H);

[0043] 13 C NMR (100MHz, CDCl 3 ): 153.7(d, J=254.3Hz), 147.3(d, J=5.9Hz), 140.8(d, J=14.1Hz), 130.4, 128.1(d, J=2.2Hz), 126.9(d, J=2.2Hz), 126.9(d, J= 2.2Hz), 126.5, 126.2(d, J=16.4Hz), 118.8(d, J=4.5Hz), 9.9, 8.5;

[0044] 19 F NMR (376MHz, CDCl 3 ):.-145.3(s)...

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Abstract

The present invention discloses a class of fluorinated isoquinoline compounds and a preparation method thereof. The fluorinated isoquinoline compound has the following structural general formula, wherein R1-R5 are respectively and independently selected from hydrogen, alkyl, naphthenic base, aryl and heterocyclic group. The preparation method comprises that: an alkyne substrate I and N-fluorobenzenesulfonimide II are subjected to a fluorine amination reaction in an anhydrous organic solvent under a basic condition in the presence of a silver catalyst, wherein the reaction formula is shown in the description, R1-R5 are respectively and independently selected from hydrogen, alkyl, naphthenic base, aryl and heterocyclic group, and R6 is selected from tert-butyl. According to the present invention, a series of fluorinated isoquinoline compounds can be prepared with simple operations under mild reaction conditions; the preparation method has advantages of low cost, good substrate compatibility and the like; and sufficient guarantee can be provided for activity screening of the fluorinated isoquinoline compounds, and wide applications of the fluorinated isoquinoline compounds in the fields of medicine, pesticides and the like can be promoted.

Description

technical field [0001] The invention relates to a class of fluoroisoquinoline compounds and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Isoquinoline can be widely used in medicine, pesticides and other fields, and can be used to manufacture drugs and high-efficiency insecticides. After oxidation, it can be made into pyridine carboxylic acid, which is used as an intermediate for synthesizing drugs, dyes, and insecticides, and as a stationary liquid for gas chromatography. . Isoquinoline derivatives widely exist in nature, and there are more than 1,000 known isoquinoline alkaloids, which are the largest class of known alkaloids. They mostly use isoquinoline or tetrahydroisoquinoline as the core, and can be subdivided into isoquinolines, benzylisoquinolines, bisbenzylisoquinolines, and apofens according to the linking group. , the original berberine class, proto class, emetine class, α-naphenanthridine cla...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/22C07D471/04
CPCC07D217/22C07D471/04
Inventor 刘国生徐涛
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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