A kind of preparation method of six-membered aryl lactone or six-membered aryl lactam compound

An aryl lactam, aryl lactone technology, applied in the direction of organic chemistry and the like, can solve the problems of unfriendly environment, lack of preparation method of six-membered aryl lactone or six-membered aryl lactam compound, lack of synthesis method and the like , to achieve the effect of high atom utilization, high yield and simple synthesis method

Active Publication Date: 2022-04-19
HARBIN INST OF TECH SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The electrolysis method provides a halogen source by oxidizing cheap sodium bromide, without the participation of transition metals, and can be realized at room temperature, but the electrochemical conditions usually require a large amount of electrolyte, which is very unfriendly to the environment
[0004] Due to the importance of the aryllactone / lactam structure, although its synthesis method has been improved, it is difficult for general, cheap, green reaction conditions without transition metal participation, especially for the conversion of sp2 carbon-hydrogen bonds to C-O at room temperature. / N key crafting methods are still lacking
[0005] Therefore, prior art still lacks the preparation method of a kind of high-yield six-membered aryl lactone or six-membered aryl lactam compound

Method used

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  • A kind of preparation method of six-membered aryl lactone or six-membered aryl lactam compound
  • A kind of preparation method of six-membered aryl lactone or six-membered aryl lactam compound
  • A kind of preparation method of six-membered aryl lactone or six-membered aryl lactam compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Add 0.36mmol of cesium iodide (CsI) and 0.3mmol of 2-phenylbenzoic acid into a 25mL reaction tube, and add 0.6mmol of MPO (4,4-dimethyl-1,2-dioxolane-3,5-dione) and 3 mL of o-dichloroethane, the molar ratio of cesium iodide to MPO is 0.6:1; use a vacuum pump to remove the gas in the reaction tube and the solvent, and fill with nitrogen, repeat the operation three times, and then place the reaction tube at 420-430nm In the stirrer irradiated with the blue light of the band LED, the reaction was detected with a thin layer chromatography (TLC) plate until the reaction of the raw materials was completed;

[0033] (2) Add 10 mL of ethyl acetate (EA) and 10 mL of water, extract with a 60 mL separatory funnel, extract the aqueous phase with EA three times (3*10 mL), combine the organic phases and wash them once with 10 mL of saturated brine, collect The organic phase was dried with anhydrous sodium sulfate;

[0034] (3) Sodium sulfate is removed by filtration, the organic...

Embodiment 2

[0042](1) Add 0.36 mmol of cesium iodide (CsI) and 0.3 mmol of N-methoxy-1,1'-biphenyl-2-amide into a 25 mL reaction tube, add 0.6 mmol of MPO (4,4-dimethyl-1 ,2-dioxolane-3,5-dione) and 3mL o-dichloroethane, remove the gas in the reaction tube and solvent with a vacuum pump, and fill with nitrogen, repeat the operation three times, then place the reaction tube in a 420-430nm band LED In a stirrer irradiated with blue light, use a thin layer chromatography (TLC) plate to detect the reaction until the reaction of the raw materials is completed;

[0043] (2) Add 10 mL of ethyl acetate (EA) and 10 mL of water, extract with a 60 mL separatory funnel, extract the aqueous phase with EA three times (3*10 mL), combine the organic phases and wash them once with 10 mL of saturated brine, collect The organic phase was dried with anhydrous sodium sulfate;

[0044] (3) Sodium sulfate is removed by filtration, the organic phase utilizes a rotary evaporator to remove the solvent to obtain a...

Embodiment 3

[0052] This example only describes the difference from Example 1, the solvent in the step (1) is different, specifically dichloromethane, and the yield of the crude product is 80%.

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Abstract

The invention discloses a preparation method of a six-membered aryl lactone or lactam compound. Specifically, a cyclic diacyl peroxide and a halogenated salt can be used to obtain an oxy-halogen bond under the condition of illumination, and then the oxy-halogen bond is exposed to the illumination. Under the conditions, it is easy to homogenize to form active free radicals, so as to prepare six-membered aryl lactone or six-membered aryl lactam compound. The invention can be completed at room temperature without the participation of transition metals, and the combination of cyclic diacyl peroxide and halide salt, as a precursor of a highly active halogen source, has the advantages of easy preparation, good thermal stability and good thermal safety. and other advantages, the synthesis method is simple and the yield is high, thereby reducing the amount of halogenated compounds in synthetic value reactions, and better achieving the goals of environmental friendliness and green chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of a ring-forming compound, in particular to a preparation method of a six-membered aryl lactone or a six-membered aryl lactam compound. Background technique [0002] Six-membered aromatic lactones or their lactams are an important part of organic compounds, not only widely found in various natural products and drugs with antibacterial, anticancer and other activities, but also an important structure of some organic functional materials such as dyes. unit. In the past, the direct chemical transformation of aromatic C-H bonds involving transition metals to construct C-N / O bonds was considered to be an effective method to achieve double bond functionalization. For example, the research group of Wang Xisheng from the University of Science and Technology of China used transition metal palladium (Pd) as a catalyst to realize the lactonization pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/80C07D221/12
CPCC07D311/80C07D221/12
Inventor 史雷昌登虎赵戎
Owner HARBIN INST OF TECH SHENZHEN GRADUATE SCHOOL
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