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A kind of method of synthesizing isoquinolinone compound or pyridone compound

A technology for isoquinolinones and compounds, applied in the field of synthesizing isoquinolinones or pyridones, to achieve the effects of easy-to-obtain raw materials, simple raw materials, and simple operations

Active Publication Date: 2022-07-05
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Olefin compounds are active and have many reaction sites, so there is a problem of regioselectivity in the reaction of transition metal-catalyzed C-H activation and alkenes

Method used

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  • A kind of method of synthesizing isoquinolinone compound or pyridone compound
  • A kind of method of synthesizing isoquinolinone compound or pyridone compound
  • A kind of method of synthesizing isoquinolinone compound or pyridone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～13

[0028] Benzamide 1a (0.2 mmol), styrene propylene 2a (0.4 mmol), catalyst (0.02 mmol), co-catalyst (0.04 mmol), and 2 mL of p-xylene were added to a 10 ml Shrek tube, and the reaction was heated for 24 hours. Then the reaction system was cooled to room temperature, filtered with sand core, washed with ethyl acetate, concentrated the solvent, and passed through the column with petroleum ether / ethyl acetate=5 / 1 to obtain the target product 3a. The specific reaction conditions and reaction results are shown in Table 1.

[0029] The reaction formula is as follows:

[0030]

[0031] Table 1 Reaction conditions and reaction results of Examples 1 to 13

[0032]

[0033]

[0034] a Reaction conditions: 1a (0.2mmol), 2a (0.4mmol), catalyst (0.02mmol), cocatalyst (0.04mmol), p-xylene (2ml), 110 ℃ air atmosphere for 24h; b separation yield; c Oxygen balloon; d 100℃.

Embodiment 14～29

[0036] In a 10ml Shrek tube, add benzamide 1 (0.2mmol), phenylpropene 2 (0.4mmol), palladium trifluoroacetate (6.6mg, 0.02mmol), copper acetate (7.3mg, 0.04mmol), 2mL of p-xylene, The reaction was stirred at 110 degrees open for 24 hours. Then the reaction system was cooled to room temperature, filtered with sand core, washed with ethyl acetate, concentrated the solvent, and passed through the column with petroleum ether / ethyl acetate = 5 / 1 or 3 / 1 to obtain the target products 3b to 3q. The reaction conditions and results are as follows:

[0037]

Embodiment 30～38

[0039] In a 10ml Shrek tube, add acrylamide 4 (0.2mmol), phenylpropene 2 (0.4mmol), palladium trifluoroacetate (6.6mg, 0.02mmol), copper acetate (7.3mg, 0.04mmol), p-xylene 2mL, 110 The reaction was stirred openly for 24 hours. Then, the reaction system was cooled to room temperature, filtered through a sand core, washed with ethyl acetate, the solvent was concentrated, and passed through the column with petroleum ether / ethyl acetate=5 / 1 or 3 / 1 to obtain the target products 5a-5i.

[0040]

[0041] The product characterization data are characterized as follows:

[0042] Isoquinolinone:

[0043] 3-Benzyl-2-((4-nitrophenyl)sulfonyl)isoquinolin-1(2H)-one(3a).Lightyellow solid; 73.9mg; 88% yield; R f = 0.44 (hexane / EtOAc = 5 / 1 as the eluent); mp = 193-194°C; 1 H NMR (400MHz, CDCl 3 )δ8.42–8.36(m,4H),7.97(dd,J=7.8,1.4Hz,1H),7.48(td,J=7.5,1.4Hz,1H),7.45–7.40(m,2H),7.37 –7.32(m, 4H), 7.16(d, J=7.6Hz, 1H), 6.82(s, 1H), 4.01(s, 2H); 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ163.1, 150...

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Abstract

The invention discloses a method for synthesizing isoquinolinone compounds or pyridone compounds. The reaction is carried out in a solvent, and after the reaction is completed, the isoquinolinone compound or the pyridone compound is obtained through post-treatment. The method has simple and easy-to-obtain raw materials, mild conditions, high conversion efficiency, high regioselectivity, high atom utilization and simple operation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing isoquinolinone compounds or pyridone compounds. Background technique [0002] Isoquinolinones and pyridones are important structural backbones in two active natural products and drug molecules. The traditional methods for synthesizing these two types of compounds include 6π-electrocyclization reaction, Larock-type heterocyclization reaction, intramolecular amine carbonyl cyclization reaction, cycloaddition reaction of o-halogenated benzamide and alkyne, etc. The disadvantages of complex materials and low atom utilization. Transition metal-catalyzed directed C-H activated cycloaddition reactions are an important method for the synthesis of complex cyclic compounds from simple and readily available substrates via a tandem reaction mode. At present, the synthesis of isoquinolinone compounds has been achieved with benzamide and alkynes or allene compounds,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/64C07D217/24
CPCC07D213/64C07D217/24Y02P20/584
Inventor 孙嫚嫚杨健国吴海建张晶
Owner TAIZHOU UNIV
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