A 1-(2-furyl)-3-(4-substituted phenyl)propene derivative and its preparation method and application
A technology of derivatives and furyl groups, applied in the field of 1--3-propene derivatives and its preparation, to achieve the effects of simple structure, good control effect and easy synthesis
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Embodiment 1
[0033] compound (C 14 h 12 ON 3 SF) preparation
[0034] (1) Synthesis of intermediate 1-(4-fluorophenyl)-3-(2-furyl)-2-propen-1-one
[0035] 0.02 mol of 4-fluoroacetophenone was dissolved in 30 mL of absolute ethanol, and 10 mL of 10% NaOH solution was added thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-fluorophenyl)-3-(2-furyl)-2-propen-1-one.
[0036] (2) Synthesis of the target compound
[0037] Dissolve 0.015 mol of thiosemicarbazide in 20 mL of 95% ethanol, and add 1.5 mL of glacia...
Embodiment 2
[0039] compound (C 14 h 12 ON 3 Preparation of SCl)
[0040] (1) Synthesis of intermediate 1-(4-chlorophenyl)-3-(2-furyl)-2-propen-1-one
[0041] 0.02 mol of 4-chloroacetophenone was dissolved in 30 mL of absolute ethanol, and 10 mL of 10% NaOH solution was added thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-Chlorophenyl)-3-(2-furyl)-2-propen-1-one.
[0042] (2) Synthesis of the target compound
[0043] Dissolve 0.015 mol of thiosemicarbazide in 20 mL of 95% ethanol, and add 1.5 mL of gl...
Embodiment 3
[0046] compound (C 14 h 12 ON 3 SBr) preparation
[0047] (1) Synthesis of intermediate 1-(4-bromophenyl)-3-(2-furyl)-2-propen-1-one
[0048] Dissolve 0.02 mol of 4-bromoacetophenone in 30 mL of absolute ethanol, and then add 10 mL of 10% NaOH solution thereto. Under stirring in an ice bath, slowly drop the mixture of 0.02mol furfural and 20mL of absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC). whether the reaction is complete. After the reaction is completed, add 3-4 times the volume of distilled water to the mixture, and adjust its pH value to neutral with 10% HCl, there is a precipitate, filter, wash, and recrystallize with absolute ethanol to obtain intermediate 1 -(4-bromophenyl)-3-(2-furyl)-2-propen-1-one.
[0049] (2) Synthesis of the target compound
[0050] Dissolve 0.015 mol of thiosemicarbazide in 20 mL of 95% ethanol, and add 1.5 mL of glacial acetic...
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