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A kind of synthetic method of quinoline compound containing tetrahydrofuran group

A technology of tetrahydrofuran and a synthetic method, applied in directions such as organic chemistry, to achieve the effects of safe operation and wide range of substrates

Active Publication Date: 2019-07-12
HUAIBEI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Here, the use of tert-butyl peroxybenzoate to promote tetrahydrofuran to produce α-carbon free radical intermediates, followed by a free radical cascade reaction with alkyne aniline compounds, and the method of synthesizing quinoline compounds containing tetrahydrofuran groups in one step have not yet been seen. Literature report

Method used

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  • A kind of synthetic method of quinoline compound containing tetrahydrofuran group
  • A kind of synthetic method of quinoline compound containing tetrahydrofuran group
  • A kind of synthetic method of quinoline compound containing tetrahydrofuran group

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Experimental program
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Effect test

Embodiment 1

[0025]

[0026] Add 1a (0.3mmol), Cs 2 CO 3 (0.6mmol), TBPB (0.6mmol), tetrahydrofuran (3mL), and stirred at 110°C for 10 hours. After the reaction, cool to room temperature, add 10mL saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10mLX3), combine the organic phases, dry with anhydrous magnesium sulfate, filter, spin dry under reduced pressure, pass column chromatography Separation and purification, the eluent used was petroleum ether / ethyl acetate (v / v=5:1), and the target product 2a was obtained as a light yellow solid with a yield of 65%. The structural characterization data of compound 2a are as follows:

[0027] 1 HNMR (400MHz, CDCl 3 ):δ=9.14(s,1H),8.15(d,J=8.8Hz,1H),7.69-7.65(m,1H),7.53-7.50(m,3H),7.41-7.40(m,2H), 7.35-7.33(m,1H),7.23-7.22(m,1H),4.79-4.75(m,1H),4.20-4.14(m,1H),3.89-3.84(m,1H),2.15-2.04(m ,2H),1.97-1.86(m,1H),1.83-1.75(m,1H);

[0028] 13 C NMR (100MHz, CDCl 3 ): δ=149.27, 147.33, 144.97, 135.81, 133.07,...

Embodiment 2

[0031]

[0032] Add 1b (0.3mmol), Cs 2 CO 3 (0.6mmol), TBPB (0.6mmol), tetrahydrofuran (3mL), and stirred at 110°C for 10 hours. After the reaction, cool to room temperature, add 10mL saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10mLX3), combine the organic phases, dry with anhydrous magnesium sulfate, filter, spin dry under reduced pressure, pass column chromatography Separation and purification, the eluent used was petroleum ether / ethyl acetate (v / v=5:1), and the target product 2b was obtained as a light yellow solid with a yield of 60%. The structural characterization data of compound 2b are as follows:

[0033] 1 H NMR (400MHz, CDCl 3 ):δ=9.13(s,1H),8.16-8.14(m,1H),7.69-7.65(m,1H),7.52-7.49(m,2H),7.43-7.40(m,1H),7.36-7.33 (m,1H),7.29-7.27(m,1H),7.18-7.15(m,1H),4.75-4.71(m,1H),4.18-4.13(m,1H),3.89-3.83(m,1H) ,2.14-2.03(m,2H),1.96-1.88(m,1H),1.84-1.74(m,1H);

[0034] 13 C NMR (100MHz, CDCl 3 ): δ=149.20, 147.29, 143.68, 1...

Embodiment 3

[0037]

[0038] Add 1c (0.3mmol), Cs 2 CO 3 (0.6mmol), TBPB (0.6mmol), tetrahydrofuran (3mL), and stirred at 110°C for 10 hours. After the reaction, cool to room temperature, add 10mL saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10mLX3), combine the organic phases, dry with anhydrous magnesium sulfate, filter, spin dry under reduced pressure, pass column chromatography Separation and purification, the eluent used was petroleum ether / ethyl acetate (v / v=5:1), and the target product 2c was obtained as a light yellow solid with a yield of 62%. The structural characterization data of compound 2c are as follows:

[0039] 1 H NMR (400MHz, CDCl 3):δ=9.13(s,1H),8.15(d,J=8.8Hz,1H),7.69-7.64(m,3H),7.44-7.40(m,1H),7.37-7.35(m,1H), 7.24-7.21(m,1H),7.12-7.10(m,1H),4.75-4.71(m,1H),4.19-4.14(m,1H),3.90-3.84(m,1H),2.15-2.04(m ,2H),1.98-1.88(m,1H),1.84-1.75(m,1H);

[0040] 13 C NMR (100MHz, CDCl 3 ): δ=149.24, 147.31, 143.64, 134.70, 133.00,...

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Abstract

The invention discloses a method for synthesizing quinoline compounds containing tetrahydrofuran groups. The synthetic method comprises the following steps: adding propynylamine compounds of a structure as shown in a formula I, tetrahydrofuran, an oxidant and alkali into a reactor, stirring and reacting at the temperature of 100-110 DEG C, performing column chromatography isolation and purification on the reaction product, thereby obtaining the quinoline compounds containing tetrahydrofuran groups. According to the method disclosed by the invention, cheap and readily available tetrahydrofuran serves as an alkylating reagent and also serves as a reaction solvent, tert-butyl peroxybenzoate (TBPB) serves as the oxidant, any metal catalyst is not needed, the operating steps are safe and simple, the reaction conditions are mild, and the substrate application range is wide. The method has innovativeness and atom economy and has potential practical value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of quinoline compounds containing tetrahydrofuran groups. Background technique [0002] Tetrahydrofuran is an important chemical raw material and is widely used as a reaction solvent. At the same time, many bioactive molecules and natural products often contain tetrahydrofuran skeleton structure, such as (-)-talaumidin, (+)-fragransin A 2 . Therefore, it is a very interesting work to directly functionalize the α-position of THF to synthesize complex molecules with potential biological activities. [0003] On the other hand, quinoline and its derivatives are an important class of organic intermediates, which exist in active natural products and synthetic drugs. Among them, the synthesis methods of quinoline compounds are mostly realized by transition metal catalysis. Recently, the one-step synthesis of functionalized quinoline compounds...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 陈巍张义成
Owner HUAIBEI NORMAL UNIVERSITY