Preparation method of (4,6-diaryl-tetrahydropyridine-3-yl)(aryl) ketone

A tetrahydropyridine and diaryl technology, which is applied in the field of preparation of ketones, can solve problems such as difficulty in obtaining and are complicated, and achieve the effects of simple operation, mild conditions and easy-to-obtain raw materials

Active Publication Date: 2019-11-05
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Pavel et al. reported the synthesis method of N-protected (4,6-diaryl-1,2,3,4-tetrahydropyridin-3-yl)(aryl)methanone in 1979, but the starting material 1,3,5-triphenyl-2-methenyl-1,5-pentanedione is more complex and difficult to obtain ((Pavel', G.V. and Tilichenko, M.N.; Khim.Geterotsikl.Soedin.ChemischerInformationsdienst 1979,10 , formula-2)

Method used

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  • Preparation method of (4,6-diaryl-tetrahydropyridine-3-yl)(aryl) ketone
  • Preparation method of (4,6-diaryl-tetrahydropyridine-3-yl)(aryl) ketone
  • Preparation method of (4,6-diaryl-tetrahydropyridine-3-yl)(aryl) ketone

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preparation example Construction

[0042] The preparation method of general (4,6-diaryl-tetrahydropyridin-3-yl) (aryl) ketone 4 specifically comprises the following steps: add aryl propynyl alcohol (0.10 mmol), solvent (0.50~1.00mL), acid (0.01~0.04mmol) and chalcone derivatives (0.10~0.20mmol), heating, reacting under reflux conditions, monitoring the reaction by TLC, waiting for the reaction of aryl propynyl alcohol After completion, add amine compound (0.10~0.20mmol), react under reflux conditions, the reaction duration is about 9~11h, then add water to the reaction solution to quench the reaction, add ethyl acetate to extract the organic phase, the obtained The organic phase was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and then concentrated on a rotary evaporator, and the obtained concentrate was purified by column chromatography.

[0043] Method 2: Preparation of (4,6-diaryl-tetrahydropyridin-3-yl)(aryl)methanone 5

[0044]The preparation method of general (4,6-diaryl-te...

Embodiment 1

[0061] (4,6-diphenyl-1-toluenesulfonyl-1,2,3,4-tetrahydropyridin-3-yl) (phenyl) ketone preparation method, the molecular formula of the target product is:

[0062]

[0063] The process of the preparation method refers to Method 1. The types and amounts of the specific aryl propynyl alcohol, solvent, catalyst, chalcone compound and amine are respectively: phenylpropynyl alcohol (0.10mmol), 1,2-dichloro Ethane (0.50 mL), bismuth triflate (0.02 mmol) and chalcone (0.12 mmol) and p-toluenesulfonamide (0.12 mmol), reaction time after addition of amine was 9 hours.

[0064] The synthesized product was characterized, and the obtained NMR data was HRMS calculated for C 31 h 29 NO 3 S([M+H] + ):494.1790; found: 494.1791.

[0065] The calculated yield of the target product was 73%.

Embodiment 2

[0067] (4,6-diphenyl-1-methylsulfonyl-1,2,3,4-tetrahydropyridin-3-yl) (phenyl) ketone preparation method, the molecular formula of the target product is:

[0068]

[0069] The process of the preparation method refers to Method 1. The consumption and types of specific aryl propargyl alcohol, solvent, acid, chalcone compound and amine are respectively: phenylpropargyl alcohol (0.10mmol), 1,2-dichloroethane Alkane (1.0 mL), copper triflate (0.03 mmol), chalcone (0.12 mmol) and benzenesulfonamide (0.12 mmol), reaction time after addition of amine was 9 hours.

[0070] The synthesized product was characterized, and the obtained NMR data was HRMS calculated for C 30 h 26 NO 3 S([M+H] + ):480.1633; found: 480.1632.

[0071] The calculated yield of the target product was 70%.

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Abstract

The invention relates to a preparation method of (4,6-diaryl-tetrahydropyridine-3-yl)(aryl)ketone. The method includes the following steps that (1) aryl propargyl alcohol, chalcone derivatives, acid and a solvent are mixed and heated for reaction under reflux conditions; (2) amine compounds are added into a reaction system where the reaction is completed for reaction for 9-17 hours under reflux conditions, and the (4,6-diaryl-tetrahydropyridine-3-yl)(aryl)ketone is obtained. Compared with the prior art, the synthesis method has the advantages that the method is simple, the condition is mild, the yield is relatively high, and the atom utilization rate can reach 100%. The synthesis method greatly optimizes synthesis of the compound and provides a new synthesis idea for the synthesis of compounds with similar structures.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of (4,6-diaryl-tetrahydropyridin-3-yl)(aryl)methanone. Background technique [0002] In some documents that have been reported, we understand that 4,6-diaryl-tetrahydropyridin-3-yl) (aryl) ketone compounds are a kind of important skeleton in organic synthesis, about the same class of compounds ( Synthesis of 2,4,6-triphenyl-3,4-dihydropyridine-1,3(2H)-diyl)bis(benzophenone) by Piper and Wright via starting materials styryl cyanide and Grignard reaction of phenyl Grignard reagent, two self-additions and one Schott-Bowman reaction finally synthesized the target compound. E. Piper and Geoger F Wright, JOC, 1950, DIO:DOI:10.1021 / ja01160a068). Through the above reaction route, we can see that this synthesis method has many steps, and requires Grignard reagents to participate in the reaction, and the reaction conditions are relatively harsh (Formula-1)....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/96C07D211/70C07D409/06
CPCC07D211/70C07D211/96C07D409/06
Inventor 殷燕张青林张华郭会峰潘万勇裴可可
Owner SHANGHAI INST OF TECH
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