A kind of isopimaric acid heterocyclic acylhydrazone derivatives and preparation method and application thereof
A technology of heterocyclic acylhydrazones and isopimaric acid, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of difficult application of acylhydrazone compounds, high reaction temperature, and long reaction time, so as to reduce time and reaction time Effect of temperature, good antibacterial activity
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Embodiment 1
[0038] A preparation method of isopimaric acid heterocyclic acylhydrazone derivatives, specifically comprising the following steps:
[0039] (1) Dissolve 15mmol of isopimaric acid in 40mL of anhydrous CH 2 Cl 2 , 20mmol oxalyl chloride was added dropwise, and the reaction was completed to obtain the CH of isopimaproyl chloride 2 Cl 2 solution; the above-prepared isopimaric acid chloride was added dropwise to anhydrous CH containing 15 mmol of 85% hydrazine hydrate and 20 mmol of triethylamine for 1 h. 2 Cl 2 The above reaction was carried out under microwave-assisted conditions, the microwave power was 400W, the time was 60min, and the reaction temperature was 15°C. After the reaction was completed, the solvent was removed, ethyl acetate was added to dissolve, the insoluble matter was removed by filtration, and the organic layer was washed with water and distilled. Remove the solvent to obtain a crude product, and the crude product is purified to obtain isopimazone hydrazi...
Embodiment 2
[0042] A preparation method of isopimaric acid heterocyclic acylhydrazone derivatives, specifically comprising the following steps:
[0043] (1) Dissolve 15mmol of isopimaric acid in 40mL of anhydrous CH 2 Cl 2 In, 20mmol oxalyl chloride was added dropwise, and the CH that the reaction finished to obtain isopimaric acid chloride 2 Cl 2 solution; add 40 mL of anhydrous CH to the isopimarosyl chloride solution prepared above 2 Cl 2 Then it was added dropwise to anhydrous CH containing 15 mmol of 85% hydrazine hydrate and 20 mmol of triethylamine over 2 h. 2 Cl 2 The above reaction was carried out under microwave-assisted conditions, the microwave power was 300 W, the reaction time was 40 min, and the reaction temperature was 10 ° C. After the reaction was completed, the solvent was removed, and ethyl acetate was added to dissolve it. The solvent is evaporated to obtain the crude product, and the crude product is purified to obtain isopimazone hydrazide;
[0044](2) the is...
Embodiment 3
[0046] The structure of the isopimaric acid group (6-trifluoromethylpyridine-3-carbaldehyde) acylhydrazone prepared in Example 1 was analyzed, and the structural formula is shown in formula 1C. The specific analysis results are as follows:
[0047] Isopimaric acid group (6-trifluoromethylpyridine-3-carbaldehyde) acylhydrazone is a white solid, figure 1 is the infrared spectrum of isopimaric acid group (6-trifluoromethylpyridine-3-carbaldehyde) acylhydrazone, by figure 1 It can be seen that 3293cm -1 The nearby peaks are attributed to the stretching vibration absorption of NH; the characteristic peak of C=O in the acylhydrazone appears at 1637cm -1 , the absorption peaks are at 1555cm-1 and 1513cm -1 The two stronger absorption peaks at the acylhydrazone belong to the characteristic absorption peak of the C=N bond and the bending vibration of the N-H bond respectively; At 1278cm -1 is a strong peak.
[0048] 1 H NMR (500MHz, CDCl 3 , the carbon atom number of the compou...
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