Thiopheno[2,3-b]quinoline derivatives and their synthesis method and application

A synthesis method and technology of derivatives, applied in the fields of botanical equipment and methods, applications, biocides, etc., can solve the problems of no research compound activity, limited reaction scope, complicated steps, etc., to achieve flexible reaction time and suitable for use. Wide-ranging, easy-to-use effects

Active Publication Date: 2017-12-08
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] These methods have following deficiencies, (1) substrate, 2-chloroquinoline, 4-hydroxyquinoline etc., are not easy to obtain; (2) reaction scope of application is not wide, and step is also more complicated; (3) there is no research on this type of compound active

Method used

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  • Thiopheno[2,3-b]quinoline derivatives and their synthesis method and application
  • Thiopheno[2,3-b]quinoline derivatives and their synthesis method and application
  • Thiopheno[2,3-b]quinoline derivatives and their synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] In a 50 ml reaction flask, add methanol 10 ml, cinnamaldehyde 1a (189 mg, 1 mmol, 1.0 eq), 2-bromo-1,3 cyclohexanedione 2 (227 mg, 1.2 mmol, 1.2 eq) and proline (57mg, 0.5mmol), stirred at 25°C for 2h, then added DBU (1.2mmol, 1.2eq), and continued to stir for 1h. Finally, the solvent was removed under reduced pressure, and the mixed solution of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 10:1) was used as eluent to carry out column chromatography to obtain thiophene[2,3-b of structural formula 3a. ] Quinoline derivative 3a (203 mg, yield 65%). The reaction equation is as follows:

[0053]

[0054] The structure of the thien[2,3-b]quinoline derivative 3a obtained above was identified by NMR and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ8.64(s,1H),8.14(d,J=8.3Hz,1H),8.06-7.88(m,2H),7.81(t,J=7.1Hz,1H),7.57(t,J=7.0 Hz,1H),3.72(s,3H),3.13(t,J=6.7Hz,2H),2.51(t,J=6.5Hz,2H),2.32-2.07(m,2H). 13 C NMR (150...

Embodiment 2

[0056] In a 50 ml reaction flask, add methanol 10 ml, cinnamaldehyde 1b (203 mg, 1 mmol, 1.0 eq), 2-bromo-1,3 cyclohexanedione 2 (227 mg, 1.2 mmol, 1.2 eq) and proline (57mg, 0.5mmol), stirred at 25°C for 2h, then added DBU (1.2mmol, 1.2eq), and continued to stir for 1h. Finally, the solvent is removed under reduced pressure, and the mixed solution of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate is 10:1) is used as eluent to carry out column chromatography to obtain thiophene[2,3-b with structural formula as 3b. ] Quinoline derivative 3b (180 mg, yield 55%). The reaction equation is as follows:

[0057]

[0058] The structure of the thien[2,3-b]quinoline derivative 3b obtained above was identified by NMR and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ8.50(s,1H),8.01(d,J=7.7Hz,1H),7.93(s,1H),7.73-7.56(m,2H),3.72(s,3H),3.10(d,J =6.4Hz, 2H), 2.56(s, 3H), 2.50(d, J=6.5Hz, 2H), 2.12(d, J=6.6Hz, 2H). 13 C NMR (150...

Embodiment 3

[0060] In a 50 ml reaction flask, add methanol 10 ml, cinnamaldehyde 1d (203 mg, 1 mmol, 1.0 eq), 2-bromo-1,3 cyclohexanedione 2 (227 mg, 1.2 mmol, 1.2 eq) and proline (57mg, 0.5mmol), stirred at 25°C for 2h, then added DBU (1.2mmol, 1.2eq), and continued to stir for 1h. Finally, the solvent was removed under reduced pressure, and the mixed solution of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 10:1) was used as eluent to carry out column chromatography to obtain thiophene[2,3-b with structural formula as 3c. ] Quinoline derivative 3c (196 mg, yield 60%). The reaction equation is as follows:

[0061]

[0062] The structure of the thien[2,3-b]quinoline derivative 3c obtained above was identified by NMR and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ8.60(s,1H),7.98(s,1H),7.90(s,1H),7.85(d,J=8.4Hz,1H),7.40(d,J=8.4Hz,1H),3.72( s,3H),3.13(t,J=7.2Hz,2H),2.62(s,3H),2.51(t,J=7.0Hz,2H),2.18-2.11(m,2H). 13 C NMR...

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Abstract

The invention discloses a thiophene[2,3-b]quinoline derivative and a synthetic method and an application thereof. The synthetic method includes the steps: in the presence of a solvent, and under catalysis of proline and DBU, carrying out a reaction of substituted cinnamic aldehyde and 2-bromo-1,3-cyclohexanedione, and posttreating the reaction product to obtain the thiophene[2,3-b]quinoline derivative. The method has the advantages of flexible reaction time, higher yield, simple operation, wide application scope and the like, and is suitable for industrialized production. The thiophene[2,3-b]quinoline derivative can be used for preparation of an antibacterial agent.

Description

technical field [0001] The invention relates to the field of synthesis of heterocyclic compounds, in particular to a thiophene [2,3-b] quinoline derivative and its synthesis method and application. Background technique [0002] Quinoline and its derivatives are an important class of heterocyclic compounds that widely exist in natural products and have important biological activities. Many quinoline derivatives have antifungal, insecticidal and other physiological effects; more and more quinoline derivatives are used in the treatment of traumatic and ischemic central nervous system (CNS) injuries and arteriosclerosis, liver disease, cerebrovascular, etc. Very useful in disease. Therefore, the synthesis of quinoline derivatives has broad application prospects. [0003] At the same time, thiophene is also a very important class of heterocyclic compounds. Its homologues or derivatives widely exist in nature and have wide application value in medicine, pesticides, dyes and fine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A01P3/00
CPCA01N43/90C07D495/04
Inventor 谢建武李丹妮卫培顺
Owner ZHEJIANG NORMAL UNIVERSITY
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