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Method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives

A technology of tetrahydropyridine and tetrahydropyridine, which is applied in the direction of organic chemistry, can solve the problems of difficult operation, industrial application limitation, and low yield, and achieve the effects of stable performance, high yield, and simple reaction operation

Inactive Publication Date: 2019-01-11
SHANDONG UNIV OF TECH
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method of synthesizing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine compounds generally requires multi-step synthesis, and is difficult to operate and the yield is very low, which has caused great harm to industrial applications. limits

Method used

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  • Method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives
  • Method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives
  • Method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives

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Experimental program
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Effect test

Embodiment 1

[0046] N-allyl-4-methyl-N-(3-methylene-5-phenyl-1-p-toluenesulfonyl-1,2,3,6-tetrahydropyridine)benzenesulfonamide: Figure 8

[0047] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.2 mmol, 49.7 mg), 2c (0.2 mmol, 82.7 mg), Pd 2 (dba) 3 (0.01 mmol, 9.1 mg) were weighed into the reaction tube in turn, evacuated to change nitrogen, and dioxane (2 mL) was added under nitrogen atmosphere, and 56 μL triethylamine was added to the pipette. Heat the reaction system to 80 o C, react for 5 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Directly add silica gel, and spin dry column chromatography to obtain brown solid 3ca (50%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.68 (d, J = 8.4 Hz,1H), 7.64 (d, J =8.0 Hz, 2H), 7.35-7.28 (m, 9H), 6.89 (s, 1H), 5.70-5.60 (m, 1H), 5.32 (s,1H), 5.14 (dd, J = 11.2, 1.2 Hz, 1H), 5.11-5.10 (m, 1H), 4.15 (s, 2H), 3.89(s, 2H), 3.76 (d, J = 6.4 Hz, 2H), 2.42 (s, 3H), 2.40...

Embodiment 2

[0049] N-allyl-N-(5-ethyl-3-methylene-1-p-toluenesulfonyl-1,2,3,6-tetrahydropyridine)-4-methylbenzenesulfonamide: Figure 9

[0050] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.2 mmol, 49.7 mg), 2d (0.2 mmol, 73.0 mg), Pd 2 (dba) 3 (0.01 mmol, 9.1 mg) were weighed into the reaction tube in turn, evacuated to change nitrogen, and dioxane (2 mL) was added under nitrogen atmosphere, and 56 μL triethylamine was added to the pipette. Heat the reaction system to 80 o C, react for 5 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Silica gel was directly added, and column chromatography was spin-dried to obtain 3da (71%) as a brown solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.42 (d, J = 8.0 Hz 2H), 7.61 (d, J = 8.0 Hz, 2H), 7.28 (d, J = 8.0 Hz, 4H), 6.31 (s, 1H), 5.67-5.57 (m, 1H),5.15 (s, 1H), 5.12-5.07 (m, 2H), 3.75 (s, 2H), 3.71 (d, J = 6.4 Hz, 2H), 3.63(s, 2H), 3.95 (s, 2H), 2.42 (s, 3H),...

Embodiment 3

[0052] N-allyl-4-methyl-N-(3-methylene-5(p-tolyl)-1-toluenesulfonyl-1,2,3,6-tetrahydropyridine)-4-benzene Sulfonamide: Figure 10

[0053] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.2 mmol, 49.7 mg), 2e (0.2 mmol, 85.5 mg), Pd 2 (dba) 3 (0.01 mmol, 9.1 mg) were weighed into the reaction tube in turn, evacuated to change nitrogen, and dioxane (2 mL) was added under nitrogen atmosphere, and 56 μL triethylamine was added to the pipette. Heat the reaction system to 80 o C, react for 5 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Silica gel was added directly, and column chromatography was spin-dried to obtain brown solid 3ea (43%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.67 (d, J = 8.4 Hz, 2H), 7.64 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 7.28 (d, J = 8.4 Hz, 2H), 7.22 (d, J = 8.0 Hz,2H), 7.15 (d, J = 7.6 Hz, 2H), 6.85 (s, 1H), 5.70-5.60 (m, 1H), 5.31(s, 1H), 5.15-5.09 (m, 2H)...

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Abstract

The invention discloses a method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives. An N-allyl-4-methoxy-N-vinylbenzenesulfonamide compound and a substituted alkenyl iodide compound, which are used as reaction raw materials, are reacted in a reaction solvent under the action of a metal palladium catalyst to obtain the polysubstituted 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives. The method has the advantages of mild reaction conditions, easily available and cheap raw materials, simple reaction operation, high yield, manure route of a synthesis substrate, and strong operability, provides a key skeleton structure for the efficient synthesis of many drug molecules and natural products, and can be widely applied to industrial large-scale production.

Description

technical field [0001] The invention specifically relates to a method for preparing 2-amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives, which belongs to the technical field of organic compound technology application. Background technique [0002] 2-Amino-3-methylene-1,2,3,6-tetrahydropyridine derivatives are very important chemical intermediates, while 2-amino-3-methylene-1,2,3, The skeleton of 6-tetrahydropyridine derivatives widely exists in various natural products and pharmaceutically active molecules, such as figure 1 Bayer's patented drugs for the treatment of asthma and Figure 4 Aminopyridone, a drug shown to improve chronic obstructive pulmonary disease, Figure 5 The indicated anti-diabetic and anti-obesity drugs and figure 2 The shown antitumor drugs all contain the skeleton structure of 2-amino-1,2,3,6-tetrahydropyridine, and the skeleton structure of 2-amino-1,2,3,6-tetrahydropyridine is in Image 6 Indicated for the treatment of Alzheimer's disease...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/96
CPCC07D211/96
Inventor 刘会闫法超梁寒冰李峻董旭孟龙迟晓晨刘青董云会
Owner SHANDONG UNIV OF TECH
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