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One-pot biomimetic synthesis of chiral tetrahydroquinolines

A tetrahydroquinoline and chiral technology, applied in the field of asymmetric catalytic synthesis, can solve the problems of difficult product separation and low atom economy, and achieve the effects of high atom economy, novel system and complete transformation

Active Publication Date: 2021-08-31
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This leads to a low atom economy of the reaction and also creates difficulties in the separation of the products

Method used

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  • One-pot biomimetic synthesis of chiral tetrahydroquinolines
  • One-pot biomimetic synthesis of chiral tetrahydroquinolines
  • One-pot biomimetic synthesis of chiral tetrahydroquinolines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0031] Optimization of conditions

[0032] Change chiral phosphoric acid, type of organic solvent, reaction temperature, molecular sieve and reaction time.

[0033] Weigh ruthenium, chiral phosphoric acid, phenanthridine, molecular sieves and 2-aminochalcone substrates in an ampoule, add 3 ml of mesitylene in the glove box, and stir in the glove box for 5 minutes. Then the mixture was transferred to an autoclave, filled with hydrogen (500 psi), and reacted at 35-50° C. for 42-72 hours. Subsequently, hydrogen gas was carefully released, the autoclave was opened, and the reaction mixture was directly purified by column chromatography using petroleum ether / ethyl acetate as eluent with a volume ratio of petroleum ether and ethyl acetate of 25:1 to give the desired target reduction product. The enantioselectivity of the products was determined by high performance liquid chromatography. The molar ratio of the 2-aminochalcone, ruthenium, chiral phosphoric acid and phenanthridine i...

Embodiment 16-31

[0038] One-pot biomimetic synthesis of chiral tetrahydroquinolines.

[0039] Weigh ruthenium, chiral phosphoric acid, phenanthridine, molecular sieves and 2-aminochalcone substrates in the ampoule, add 3 ml of mesitylene in the glove box, and stir in the glove box for 5 minutes. Then the mixture was transferred to an autoclave, filled with hydrogen (500 psi), and reacted at 40° C. for 72 hours. Subsequently, hydrogen gas was carefully released, the autoclave was opened, and the reaction mixture was directly purified by column chromatography using petroleum ether / ethyl acetate as eluent with a volume ratio of petroleum ether and ethyl acetate of 25:1 to give the desired target reduction product. The enantioselectivity of the products can be determined using high performance liquid chromatography. The molar ratio of the 2-aminochalcone, ruthenium, chiral phosphoric acid and phenanthridine is 1:0.04:0.1:0.2. 16 different examples were obtained by changing the types of raw mate...

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Abstract

The invention provides a one-pot method for biomimetic synthesis of chiral tetrahydroquinoline compounds, starting from the simple and easy-to-obtain 2-aminochalcone substrates, and through one-pot method for biomimetic synthesis of chiral tetrahydroquinoline compounds , and its enantiomeric excess can reach 92%. The invention is simple and practical in operation, high in enantioselectivity, good in yield, environmentally friendly and green, mild in reaction conditions, and has potential practical application value.

Description

technical field [0001] The invention relates to a one-pot method for biomimetic synthesis of chiral tetrahydroquinoline compounds, belonging to the field of asymmetric catalytic synthesis. [0002] technical background [0003] Tetrahydroquinoline is an important and ubiquitous structural unit widely present in many bioactive molecules, natural products and drug molecules. These tetrahydroquinoline-containing biomolecules have a variety of excellent biological activities: such as antihypertensive, antidiabetic, antibacterial and antimalarial activities (I-II). In the field of medicine, molecules containing a tetrahydroquinoline skeleton can also be used as androgen receptor agonists and progesterone receptor antagonists (III-IV). In addition, molecules containing tetrahydroquinoline skeletons are also a class of valuable synthetic intermediates, which can be used for the synthesis of nitrogen-containing ligands in organic chemistry and as multifunctional dyes for industrial ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D215/12C07D405/04
CPCC07B2200/07C07D215/06C07D215/12C07D215/14C07D405/04Y02P20/584
Inventor 周永贵赵子彪孙蕾
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI