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Beta-trifluoromethyl enamine derivative and preparation method thereof

A technology of trifluoromethylenamine and trifluoromethyl, which is applied in the field of β-trifluoromethylenamine derivatives and their preparation, can solve the problems of high technical requirements, difficult to obtain, expensive and the like, and achieves reaction operation And the post-processing process is simple, the reaction conditions are mild, and the various effects

Active Publication Date: 2017-11-07
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the above methods are only applicable to the trifluoromethylation reaction of terminal enamines and cyclic enamines.
Moreover, the trifluoromethylation reaction using the above method requires the use of expensive photocatalysts, peroxides, special reagents, or toxic solvents such as acetonitrile
The above method also has the disadvantages that the range of raw materials is relatively single, and it is not easy to obtain, and a large amount of metal catalysts are used in the reaction process.
Accordingly, it can be inferred that the scope of substrate application of the above method is narrow, the operation technology requirements are high, and the reaction scale should not be too large.

Method used

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  • Beta-trifluoromethyl enamine derivative and preparation method thereof
  • Beta-trifluoromethyl enamine derivative and preparation method thereof
  • Beta-trifluoromethyl enamine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of Example 1N-(3,3,3-trifluoro-2-phenyl-1-propenyl)benzamide (2a)

[0045]

[0046] With disodium hydrogen phosphate as base, without adding nitrogen-containing ligand (reaction (1)-(3)) as the control experiment of adding nitrogen-containing ligand (reaction (4)-(6)), specifically as follows:

[0047] (1) Weigh N-(2-phenyl-1-vinyl)benzamide 1a (0.059g, 0.25mmol), Togni reagent (0.119g, 0.375mmol), cuprous chloride (0.003g, 0.025mmol) ) was dissolved in 4 mL of 1,2-dichloroethane (DCE), disodium hydrogen phosphate (0.071 g, 0.5 mmol). The mixture was heated to 90°C, and the reaction was followed by TLC until the reaction was completely completed. After the reaction, the crude product was separated and purified by silica gel column chromatography (n-hexane:acetone=5:1) to obtain compound 2a. Isolated yield was 52%.

[0048] (2) Weigh N-(2-phenyl-1-vinyl)benzamide 1a (0.059g, 0.25mmol), Togni reagent (0.119g, 0.375mmol), cuprous bromide (0.004g, 0.025mmol)...

Embodiment 2

[0066] Example 2 4-Methyl-N-(3,3,3-trifluoro-2-phenyl-1-propenyl)benzamide (2b)

[0067]

[0068] Weigh 4-methyl-N-(2-phenyl-1-vinyl)benzamide 1b (0.060g, 0.25mmol), Togni reagent (0.119g, 0.375mmol), cuprous iodide (0.005g, 0.025mmol) was dissolved in 4mL 1,2-dichloroethane (DCE), disodium hydrogen phosphate (0.071g, 0.5mmol), DMEDA (0.005g, 0.05mmol). The mixture was heated to 90°C, and the reaction was followed by TLC until the reaction was completely completed. After the reaction, the crude product was separated and purified by silica gel column chromatography (n-hexane:acetone=5:1) to obtain compound 2b. Isolated yield was 68%.

[0069] 2b: 68% yield; 1 H NMR (400MHz, CDCl 3 )δ: 7.94(d, J=10.4Hz,1H),7.77(d,J=10.1Hz,1H),7.55–7.46(m,5H),7.40(d,J=6.9Hz,2H),7.22( d,J=8.0Hz,2H),2.38(s,3H); 13 CNMR (101MHz, CDCl 3 )δ: 164.24(s), 143.65(s), 130.10(s), 129.62(s), 129.59(s), 129.46(s), 129.37(s), 128.89(s), 127.20(s), 126.73( q, J=7.07Hz), 124.19(q, J=270.7Hz), 112.51(q...

Embodiment 3

[0070] Example 3 Synthesis of 4-methoxy-N-(3,3,3-trifluoro-2-phenyl-1-propenyl)benzamide (2c)

[0071]

[0072] Weigh 4-methoxy-N-(2-phenyl-1-vinyl)benzamide 1c (0.063g, 0.25mmol), Togni reagent (0.119g, 0.375mmol), cuprous iodide (0.005g , 0.025mmol) was dissolved in 4mL 1,2-dichloroethane (DCE), disodium hydrogen phosphate (0.071g, 0.5mmol), DMEDA (0.005g, 0.05mmol). The mixture was heated to 90°C, and the reaction was followed by TLC until the reaction was completely completed. After the reaction, the crude product was separated and purified by silica gel column chromatography (n-hexane:acetone=5:1) to obtain compound 2c. Isolated yield was 61%.

[0073] 2c: 61% yield; 1 H NMR (400MHz, CDCl 3 )δ: 7.96–7.83(m,1H),7.74(d,J=11.3Hz,1H),7.56(t,J=7.9Hz,2H),7.53–7.43(m,3H),7.40(d,J =7.1Hz, 2H), 6.89(d, J=8.7Hz, 2H), 3.82(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ: 163.68(s), 163.23(s), 130.18(s), 129.62(s), 129.33(s), 129.19(s), 126.83(q, J=7.0Hz), 124.39(s), 124.21( q, J=270....

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Abstract

The invention relates to a beta-trifluoromethyl enamine derivative. The structural general formula of the beta-trifluoromethyl enamine derivative is as follows: formula (shown in the description), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 are independently selected from hydrogen, alkyl, alkoxy, halogen or trifluoromethyl. The invention further provides a preparation method of the beta-trifluoromethyl enamine derivative. The preparation method comprises the step of reacting by virtue of an N-(2-phenyl-1-vinyl)benzamide derivative and a tongi reagent at 80-100 DEG C in an organic solvent in the presence of alkali, a ligand and a copper salt catalyst, so as to obtain the beta-trifluoromethyl enamine derivative. According to the preparation method, several beta-trifluoromethyl enamine derivatives can be obtained in a high yield manner; reaction conditions are mild, and the operation and post-treatment processes are simple, and the preparation method is applicable to large-scale production.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a β-trifluoromethylenamine derivative and a preparation method thereof. Background technique [0002] Trifluoromethyl is a very important structural motif in many agricultural chemicals and pharmaceuticals because it can effectively improve the physical and chemical properties of bioactive compounds, such as membrane permeability, bioavailability and metabolic stability. Meanwhile, amines with β-trifluoromethyl groups are important structural motifs in many bioactive compounds and are useful intermediates for the synthesis of fluorinated amino acids and peptidases. Therefore, it is of great significance to develop methods for synthesizing β-trifluoromethylamine compounds and derivatives thereof. [0003] At present, the synthetic methods of β-trifluoromethylenamine derivatives mainly contain the following types: [0004] (1) Under the catalysis of light, trifluoromethylsulfonyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/66C07C235/60C07C233/73C07C231/12C07C231/24C07B37/04
CPCC07B37/04C07C231/12C07C231/24C07C233/66C07C233/73C07C235/60
Inventor 曾润生王清邹建平
Owner SUZHOU UNIV
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