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
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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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