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A kind of 1,2,3,4-tetrahydroquinoline derivative and preparation method thereof

A hydrogen and compound technology, which is applied in the field of 1,2,3,4-tetrahydroquinoline derivatives and their preparation, can solve problems such as difficulty in controlling stereoselectivity, and achieve a wide range of substrate use and large industrialization potential , the effect of mild reaction conditions

Active Publication Date: 2017-06-16
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For 1,2,3,4-tetrahydroquinoline derivatives shown in formula I, the existing preparation method of direct hydrogenation of quinoline derivatives has mild reaction conditions and high yields, but it is difficult to control the stereoselectivity sex, enantioselectivity

Method used

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  • A kind of 1,2,3,4-tetrahydroquinoline derivative and preparation method thereof
  • A kind of 1,2,3,4-tetrahydroquinoline derivative and preparation method thereof
  • A kind of 1,2,3,4-tetrahydroquinoline derivative and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1, synthesis (+ / -)-(2S,3R,4R)-3-methyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline and (+)-( 2S,3R,4R)-3-Methyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline

[0071] (1) Synthesis of (+ / -)-(2S,3R,4R)-3-methyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline (see structural formula I-a)

[0072]

[0073] Add HB (C 6 f 5 ) 2 (0.02mmol, 0.0069g), styrene (0.02mmol, 0.0021g), toluene (0.6mL), stirred at room temperature for 10 minutes, then added 3-methyl-2,4-diphenylquinoline (formula Ⅱ-a Shown) (0.1180g, 0.4mmol), toluene (0.2mL), then close the reactor, replace the hydrogen three times, and finally fill the hydrogen with a pressure of 20bar, place the reactor in an oil bath at 40°C and stir for 20 hours, Then the hydrogen was evacuated, spin-dried and column chromatography (eluent: petroleum ether: ethyl acetate = 20 / 1, v / v) was a white solid with a yield of 94%.

[0074] The structural verification results are as follows: IR (film): 3370, 1605, 1494, 1477cm -1 ; 1...

Embodiment 2

[0082] Example 2. Synthesis of (+ / -)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetra Hydroquinoline and (+)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

[0083] (1) Synthesis of (+ / -)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydro Quinoline (see structural formula I-b)

[0084] Add HB (C 6 f 5 ) 2 (0.02mmol, 0.0069g), styrene (0.02mmol, 0.0021g), toluene (0.6mL), stirred at room temperature for 10 minutes, then added 3-methyl-4-phenyl-2-(4-methoxybenzene Base)-quinoline (shown in formula II-b) (0.1300g, 0.4mmol), toluene (0.2mL), then close the reactor, pump out the hydrogen for three times, and finally fill in the hydrogen with a pressure of 20bar, and place the reactor Stir in an oil bath at 40°C for 20 hours, then evacuate the hydrogen, spin dry and perform column chromatography (eluent: petroleum ether: ethyl acetate = 20 / 1, v / v) as a white solid with a yield of >99% .

[0085]

[0086] The stru...

Embodiment 3

[0094] Example 3. Synthesis of (+ / -)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methylphenyl)-1,2,3,4-tetrahydro Quinoline and (+)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methylphenyl)-1,2,3,4-tetrahydroquinoline

[0095] (1) Synthesis of (+ / -)-(2S,3R,4R)-3-methyl-4-phenyl-2-(4-methylphenyl)-1,2,3,4-tetrahydroquinone Phenyl (see structural formula I-c)

[0096]

[0097] Add HB (C 6 f 5 ) 2 (0.02mmol, 0.0069g), styrene (0.02mmol, 0.0021g), toluene (0.6mL), stirred at room temperature for 10 minutes, then added 3-methyl-4-phenyl-2-(4-methylphenyl )-quinoline (shown in formula II-c) (0.1236g, 0.4mmol), toluene (0.2mL), then close the reactor, pump out the hydrogen for three times, finally charge into the hydrogen with a pressure of 20bar, place the reactor in Stir in an oil bath at 40°C for 20 hours, then evacuate the hydrogen, spin dry and perform column chromatography (eluent: petroleum ether: ethyl acetate = 20 / 1, v / v) as a white solid with a yield of 91%.

[0098] The structure con...

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Abstract

The invention discloses a 1, 2, 3, 4-tetradroquinoline derivative and a method for preparing the same. The method for preparing the1, 2, 3, 4-tetradroquinoline derivative which can be a chemical compound shown by a formula I includes a step of enabling a chemical compound shown in a formula II and hydrogen to carry out reduction reaction under the catalysis effects of HB(C<6>F<5>)<2> and styrene to obtain the chemical compound shown in the formula I. Alternately, the method for preparing the 1, 2, 3, 4-tetradroquinoline derivative which can be an optically active chemical compound shown in a formula I includes a step of enabling the chemical compound shown in the formula II and hydrogen to carry out reduction reaction under the catalysis effects of the HB(C<6>F<5>)<2> and a chemical compound shown in a formula III to obtain the optically active chemical compound shown in the formula I. The 1, 2, 3, 4-tetradroquinoline derivative and the method have the advantages that the HB(C<6>F<5>)<2> and the styrene are used as catalysts, quinoline derivatives with different structures are used as substrates, accordingly, the high-yield all-cis 1, 2, 3, 4-tetradroquinoline derivative can be synthesized, and the stereoselectivity of products can be controlled; alternately, the HB(C<6>F<5>)<2> and chiral diene are used as catalysts, the quinoline derivatives with the different structures are used as the substrates, accordingly, the high-yield optically active 1, 2, 3, 4-tetradroquinoline derivative can be synthesized, and the enantioselectivity of products can be controlled.

Description

technical field [0001] The invention relates to a 1,2,3,4-tetrahydroquinoline derivative and a preparation method thereof, belonging to the field of organic synthesis. Background technique [0002] Tetrahydroquinoline is a substance with important application value in medicine, agriculture and other fields. Many drugs contain tetrahydroquinoline skeleton or are derived from tetrahydroquinoline. In organic chemistry, tetrahydroquinoline can also be used as an important ligand skeleton and reaction intermediate. As a derivative of tetrahydroquinoline, the 1,2,3,4-tetrahydroquinoline derivative shown in formula I plays a very important role in organic synthesis and has potential biological activity. [0003] [0004] At present, there are many methods for preparing tetrahydroquinoline in organic synthesis, mainly through the formation reaction of intramolecular C-N bonds, or the direct hydrogenation reaction of simple quinoline derivatives. For 1,2,3,4-tetrahydroquinoline ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D215/12C07D215/18C07D409/04
CPCC07D215/06C07D215/12C07D215/14C07D215/18C07D409/04
Inventor 杜海峰张振华
Owner INST OF CHEM CHINESE ACAD OF SCI
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