Benzoyl pyrazolone conjugates, and preparation method and application thereof
A technology of phthalide pyrazolone and conjugates, which is applied in the field of phthalide pyrazolone conjugates, their preparation and application, and can solve the problems of imbalance, many toxic and side effects, and single action target
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Embodiment 1
[0027] Example 1 General method for the preparation of 6-amino-3-substituted phthalides (2)
[0028] Add 5.0 mmol of the corresponding 6-nitro-3-substituted phthalide compound (1) and 50 ml of methanol into the reaction flask, stir and dissolve at room temperature, then add 10% Pd-C catalyst (the amount is 10% of the weight of the substrate %), the reaction bottle was replaced with hydrogen three times, and stirred and reacted at room temperature and pressure for 8 hours; after the reaction, filtered, a small amount of methanol washed the filter cake, and after the filtrate and washing liquid were combined, the solvent was evaporated under reduced pressure to obtain 6- The yield of amino-3-substituted phthalide compound (2) was quantified, and it was directly used in the next step without purification.
Embodiment 2
[0029] Example 2 General method for the preparation of 6-hydrazino-3-substituted phthalides (3)
[0030] Add 3.0 mmol of the corresponding 6-amino-3-substituted phthalide compound (2), 2.0 ml of concentrated hydrochloric acid and 5 ml of deionized water into the reaction flask, stir at room temperature until the solids are completely dissolved, and cool in an ice-salt bath to 0~ 5°C, add NaNO dropwise 2 The aqueous solution is 3.6 mmol, and the reaction temperature is controlled below 5°C. After dropping, continue to keep stirring at 0-5°C for 30 minutes to obtain the diazonium salt solution.
[0031] Slowly add the entire amount of the above-mentioned diazonium salt solution dropwise into a mixed solution made of 10.0 mmol sodium hydroxide, 12.0 mmol sodium metabisulfite and 8.0 ml deionized water. After the drop is completed, heat up and reflux to stir for about 3 hours, and then suction filter while it is hot. After cooling, the filtrate was neutralized to alkaline with 5%...
Embodiment 3
[0032] Example 3 General method for the preparation of phthalide pyrazolone conjugates (I)
[0033] Add 1.0 mmol of 6-hydrazino-3-substituted phthalide compound (3) prepared in Example 2, 1.1 mmol of ethyl acetoacetate (or ethyl trifluoroacetoacetate) and ethanol (or Acetic acid) 10 ml, heated and refluxed and stirred for 4.0 to 8.0 hours (the reaction process was tracked by TLC); after the reaction, the solvent was evaporated under reduced pressure, 20 mL of deionized water was added to the residual liquid, and extracted three times with 60 mL of ethyl acetate , the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and filtered, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: petroleum ether: ethyl acetate=2:1 v / v), the corresponding phthalide pyrazolone conjugates (I) were obtained, the yield was 30.0%-65.0%, and its chemical structure was ...
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