Benzofuranone/ naphthofuranone aryl imine compound and synthetic method thereof
A technology of furanone aryl imine and synthesis method, which is applied in the field of benzo/naphthofuranone aryl imine compounds and their synthesis, can solve the problems of harsh reaction conditions and unproposed applicability, and achieve functional group compatibility Strong, easy to separate, high yield effect
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[0027] Synthesis example 1
[0028] (Z)-1-(4-Methylphenylimine)naphtho[2,1-b]furan-2-one
[0029] Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-methylphenyl)ethyl glycinate, solvent 1,2-dichloroethane into a 25mL reactor filled with oxygen 2.0mL. Heat to 120°C, continue stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill under reduced pressure to remove the solvent. The crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 75%. 1 H NMR(400M,CDCl 3 ): δ8.96(d,J=8.4Hz,1H), 8.06(d,J=8.8Hz,1H), 7.88(d,J=8.0Hz,1H), 7.68(t,J=7.6Hz,1H ), 7.54-7.51 (m, 1H), 7.29 (d, J=8.8 Hz, 1H), 7.26-7.22 (m, 2H). 7.09-7.07 (m, 2H), 2.40 (s, 3H).
Example Embodiment
[0030] Synthesis Example 2
[0031] (Z)-1-(4-tert-butylphenylimine)naphtho[2,1-b]furan-2-one
[0032] Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-tert-butylphenyl) glycine ethyl ester, and solvent 1,2-dichloroethyl into a 25mL reactor filled with oxygen. Alkane 2.0mL. Heat to 120°C, continue stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill under reduced pressure to remove the solvent. The crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 82%. 1 H NMR(400M,CDCl 3 ): δ8.94(d,J=8.4Hz,1H), 8.03(d,J=8.8Hz,1H), 7.86(d,J=8.0Hz,1H), 7.66(t,J=7.6Hz,1H ), 7.50 (t, J = 7.6 Hz, 1H), 7.44 (d, J = 7.6 Hz, 2H), 7.28-7.24 (m, 1H), 7.14 (d, J = 7.6 Hz, 2H), 1.36 (s ,9H).
Example Embodiment
[0033] Synthesis Example 3
[0034] (Z)-1-(4-Methoxyphenylimine)naphtho[2,1-b]furan-2-one
[0035] Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-methoxyphenyl) glycine ethyl ester, solvent 1,2-dichloroethane into a 25mL reactor filled with oxygen Alkane 2.0mL. Heat to 120°C, continue stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill under reduced pressure to remove the solvent. The crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 80%. 1 H NMR(400M,CDCl 3 ): δ8.99(d,J=8.4Hz,1H), 8.03(d,J=8.8Hz,1H), 7.88(d,J=8.4Hz,1H), 7.68(t,J=7.6Hz,1H ), 7.52 (t, J = 7.6 Hz, 1H), 7.34-7.26 (m, 3H), 6.97 (d, J = 8.8 Hz, 2H), 3.09 (s, 3H).
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