A kind of 3-acyl dihydroquinoline derivative and its preparation method and application

A technology for acyl dihydroquinoline and derivatives, which is applied in the field of 3-acyl dihydroquinoline derivatives and their preparation, can solve the problems of rare raw materials, low yield, many side reactions, etc., and achieves high purity and yield High, atom-economical effects

Active Publication Date: 2022-02-18
GUANGDONG MEDICAL UNIV +1
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing methods for synthesizing 3-acyldihydroquinoline derivatives are all based on the reaction of anthraniloyl derivatives and β-acyl compounds, which require multi-step synthesis, and the yield is low, raw materials are rare, and side reactions are many and other shortcomings, there is no very effective and widely adaptable method

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of 3-acyl dihydroquinoline derivative and its preparation method and application
  • A kind of 3-acyl dihydroquinoline derivative and its preparation method and application
  • A kind of 3-acyl dihydroquinoline derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] In acetonitrile, add the above formula (II) diaminoacetophenone, (III) 3-butyn-2-one and (IV) p-toluenesulfonyl azide, cuprous iodide (CuI), three [(1- Benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA), then stirred and sealed the reaction at room temperature for 24 hours.

[0044] Wherein, the molar ratio of the compound of formula (II) to cuprous iodide (CuI) is 1:0.05; the compound of formula (II) and three [(1-benzyl-1H-1,2,3-triazole-4- The molar ratio of base) methyl] amine (TBTA) is 1:0.1; The molar ratio of formula (II) compound and (III), (IV) compound is 1:1:1; And in millimole (mmol) and milliliter (mL), the ratio of the compound of the formula (II) to acetonitrile is 1:5.

[0045] After the reaction was completed, the reaction system was naturally cooled to room temperature, a mixture of ethyl acetate and saturated saline was added in an equal volume ratio, shaken and extracted 3 times, the organic layer was collected, dried, and concentrated by ...

Embodiment 2

[0050]

[0051] In acetonitrile, add the above formula (II) diaminoacetophenone, (III) 3-butyn-2-ketone and (IV) benzylsulfonyl azide, cuprous iodide (CuI), three [(1- Benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA), then warmed to 40 °C, and stirred and sealed the reaction at this temperature for 12 hours.

[0052] Wherein, the molar ratio of the compound of formula (II) to cuprous iodide (CuI) is 1:0.2; the compound of formula (II) and three [(1-benzyl-1H-1,2,3-triazole-4- The molar ratio of base) methyl] amine (TBTA) is 1:0.2; The molar ratio of formula (II) compound and (III), (IV) compound is 1:2:2; And in millimole (mmol) and milliliter (mL), the ratio of the compound of the formula (II) to acetonitrile is 1:8.

[0053] After the reaction was complete, the reaction system was naturally cooled to room temperature, extracted twice at a volume ratio of water to ethyl acetate of 3:1, and the upper layer liquid was collected and washed with anhydrous Na 2 SO 4 After dr...

Embodiment 3

[0058]

[0059] In acetonitrile, add the above formula (II) 2-amino-5-chloroacetophenone, (III) 3-butyne-2-one and (IV) p-toluenesulfonyl azide, cuprous iodide (CuI) , Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA), then heated to 30° C., and stirred and sealed at this temperature for 8 hours.

[0060] Wherein, the molar ratio of the compound of formula (II) to cuprous iodide (CuI) is 1:0.15; the compound of formula (II) and three [(1-benzyl-1H-1,2,3-triazole-4- The molar ratio of base) methyl] amine (TBTA) is 1:0.3; The molar ratio of formula (II) compound and (III), (IV) compound is 1:1.5:1.5; And in millimole (mmol) and milliliter (mL), the ratio of the compound of the formula (II) to acetonitrile is 1:6.

[0061] After the reaction was complete, the reaction system was naturally cooled to room temperature, extracted once at a volume ratio of water to ethyl acetate of 5:1, and the upper liquid was collected and washed with anhydrous Na 2 SO 4 After drying, t...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a 3-acyl dihydroquinoline derivative and its preparation method and application, comprising the following steps: adding an anthraniloyl compound, a terminal alkyne ketone compound, a sulfonyl azide and an organic ligand into an organic solvent , react under the action of a catalyst to obtain 3-acyl dihydroquinoline derivatives. The present invention is synthesized by a one-pot method, has many advantages such as high product yield, high purity, and high atom economy, has good scientific research value and application prospect, and provides a new route for the preparation of 3-acyldihydroquinoline derivatives, which can It plays an important role in the fields of pharmaceutical intermediates and pesticide intermediates, reduces production costs, and has good application value and potential in industry and scientific research.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a 3-acyldihydroquinoline derivative and its preparation method and application. Background technique [0002] Dihydroquinolines widely exist in natural products, and their derivatives have various biological activities, especially 3-acyldihydroquinoline derivatives have a variety of potential biological activities, such as anti-inflammatory, anti-fungal, anti-bacterial, anti-tumor (J. Nat. Prod. 2020, 83, 2854-2866; Phytochemistry. 2020, 169, 112177) and other biological activities have always been the research hotspots of scholars at home and abroad. The existing methods for synthesizing 3-acyldihydroquinoline derivatives are all based on the reaction of anthraniloyl derivatives and β-acyl compounds, which require multi-step synthesis, and the yield is low, raw materials are rare, and side reactions are many And other shortcomings, there is no very effective ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38C07D215/54
CPCC07D215/38C07D215/54
Inventor 罗喜爱周子彤杨渭光戚怡罗辉
Owner GUANGDONG MEDICAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap