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Method for synthesizing isoquinolinone compounds or pyridone compounds

A technology for isoquinolinones and compounds, applied in the field of synthesizing isoquinolinones or pyridones, achieving the effects of mild conditions, simple raw materials, and easy availability of raw materials

Active Publication Date: 2021-07-23
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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  • Method for synthesizing isoquinolinone compounds or pyridone compounds
  • Method for synthesizing isoquinolinone compounds or pyridone compounds
  • Method for synthesizing isoquinolinone compounds or pyridone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～13

[0028] Add benzamide 1a (0.2mmol), phenylpropylene 2a (0.4mmol), catalyst (0.02mmol), cocatalyst (0.04mmol), p-xylene 2mL to a 10ml Shrek tube, and heat to react for 24 hours. Then the reaction system was cooled to room temperature, sand core filtered, washed with ethyl acetate, the solvent was concentrated, and the target product 3a was obtained by passing through the column with petroleum ether / ethyl acetate=5 / 1. The specific reaction conditions and reaction results are shown in Table 1.

[0029] The reaction formula is as follows:

[0030]

[0031] The reaction condition and reaction result of table 1 embodiment 1~13

[0032]

[0033]

[0034] a Reaction conditions: 1a (0.2mmol), 2a (0.4mmol), catalyst (0.02mmol), co-catalyst (0.04mmol), p-xylene (2ml), 110°C under air atmosphere for 24h; b Separation yield; c oxygen balloon; d 100°C.

Embodiment 14～29

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

[0037]

Embodiment 30～38

[0039] Add acrylamide 4 (0.2mmol), phenylpropylene 2 (0.4mmol), palladium trifluoroacetate (6.6mg, 0.02mmol), copper acetate (7.3mg, 0.04mmol), p-xylene 2mL, 110 The reaction was carried out under open stirring for 24 hours. Then the reaction system was cooled to room temperature, sand core filtered, washed with ethyl acetate, the solvent was concentrated, and the target products 5a-5i were obtained by passing through the column with petroleum ether / ethyl acetate=5 / 1 or 3 / 1.

[0040]

[0041] Product characterization data are characterized as follows:

[0042] Isoquinolinones:

[0043] 3-Benzyl-2-((4-nitrophenyl)sulfonyl)isoquinolin-1(2H)-one(3a).Lightyellow solid; 73.9 mg; 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, 150.6, 145.3, 137...

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Abstract

The invention discloses a method for synthesizing isoquinolinone compounds or pyridone compounds. The method comprises the following step: reacting benzamide compounds or acrylamide compounds with allyl benzene compounds in an organic solvent under the action of a palladium catalyst and a cocatalyst, and after the reaction is finished, carrying out post-treatment to obtain the isoquinolinone compounds or the pyridone compounds. The method has the advantages of simple and easily available raw materials, mild conditions, efficient conversion, high regioselectivity, high atom utilization rate and simple operation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing isoquinolone compounds or pyridone compounds. Background technique [0002] Isoquinolones and pyridones are two important structural skeletons in 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 are the complexity of the material and the low utilization rate of atoms. 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 tandem reaction modes. At present, the synthesis of isoquinolinone compounds has been realized by using benz...

Claims

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Application Information

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Patent Type & Authority Applications(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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