A kind of method for preparing peninoan compound

The technology of a compound and a halogenating agent is applied in the field of synthesis of peninolide compounds, and can solve the problems of high cost, complicated process, cumbersome method steps and the like

Active Publication Date: 2021-10-22
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, although the synthesis method of this type of compound has been reported, the existing method steps are cumbersome, the process is complicated, and the cost is high. The acetone cyanohydrin used in the reagent used in the reaction is a highly toxic chemical, which is extremely harmful to the human body and the environment. Big

Method used

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  • A kind of method for preparing peninoan compound
  • A kind of method for preparing peninoan compound
  • A kind of method for preparing peninoan compound

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Embodiment

[0031] 4-Hydroxyquinoline-3-carboxylic acid ethyl ester

[0032] Weigh aniline (1.02 mL, 0.011 mol) and diethyl ethoxymethylenemalonate (0.5-2 eq) into ethanol, heat at 100-200°C for three hours, cool to room temperature, add phenetole , heated at 100-200°C for 30min, cooled to room temperature, after the reaction was completed, added ice water, extracted with ethyl acetate (100mL×2), combined the organic phases, washed the organic phases with saturated brine, dried over anhydrous sodium sulfate, and filtered , the organic phase was concentrated, and the residue was subjected to silica gel column chromatography to obtain the product as a white solid 1.6g (76% yield);

[0033] ESI-MS m / z 218.32 [M+H] +

[0034] 1 H NMR (500 MHz, DMSO-d 6 ): 10.62 (brs, 1H), 8.80 (s, 1H), 8.46-7.78(m, 4H), 4.10 (q, J =7.1 Hz, 2H), 1.30 (t, J =7.1 Hz, 3H).

[0035] 4-Chloroquinoline-3-carboxylic acid ethyl ester

[0036] Weigh 4-hydroxyquinoline-3-carboxylic acid ethyl ester (1.6g, 7.3mmol...

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Abstract

The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of penicinotam compounds. The present invention uses aniline and ethoxymethylene malonate as starting materials through condensation reaction, Gould-Jacob reaction to form quinoline parent ring, and then through bromination and Suzuki reaction to obtain 2-(1-(tert Butoxycarbonyl)‑1 H -pyrrole-2-yl)-4-chloroquinoline-3-formic acid ethyl ester intermediate, and finally prepare the target product peninoan through ring-closing reaction.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a new method for synthesizing a perininool compound represented by formula I. Background technique [0002] Literature Shao, Chang-Lun; Wang, Chang-Yun; Gu, Yu-Cheng; Wei, Mei-Yan;Pan, Jia-Hui; Deng, Dong-Sheng; She, Zhi-Gang; Lin, Yong-Cheng. Bioorganic & Medicinal Chemistry Letters (2010), 20(11), 3284-3286. The structure and insecticidal activity of the active natural product penicinotam are disclosed. [0003] Chinese patent CN 2009100183213 discloses the compounds shown below as insecticides. [0004] [0005] Abe, Masaki; Imai, Tetsuya; Ishii, Naoki; Usui, Makio. Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities. Bioscience, Biotechnology, and Biochemistry (2006), 70(1), 303-306 discloses following compound, a kind of synthetic method of quinolactacide. [0006] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61P1/00A61P3/00A61P7/00A61P13/00
CPCC07D471/04
Inventor 邵长伦李德宝焦亚函
Owner OCEAN UNIV OF CHINA
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