Parazole and isoxazole derivative and application thereof
A technology of isoxazole and derivatives, applied in the field of 5-(4-substituted arylamide)-isoxazole-3-carboxylic acid ethyl ester compounds, isoxazole derivatives and their applications, can solve the problem of specificity Weakness, low activity, etc.
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Embodiment 1～5
[0124] Synthesis of 5-(4-substituted arylamide)-1H-pyrazole-3-carboxylic acid ethyl ester Ⅱ compound (compound Ⅱ-1);
[0125] (1) Synthesis of ethyl 4-(4-nitro)phenyl-2,4-dioxo-butyrate (intermediate 2)
[0126] In a dry reaction flask, add 400 mL of absolute ethanol and 2.3 g of sodium metal to prepare a sodium ethoxide solution. Add 8.3g of p-nitroacetophenone to the sodium ethoxide solution, stir at room temperature until the solid is completely dissolved, then add 15.74g of diethyl oxalate, react for 6 hours, add acetic acid to adjust the pH to 6.5, and filter with suction to obtain a yellow solid, which is Intermediate 2, dried to obtain 11.7g;
[0127] (2) Synthesis of ethyl 5-(4-nitrophenyl)-1H-pyrazole-3-carboxylate (intermediate 3)
[0128] Intermediate 2 (11.7g, 0.044mol) and hydrazine hydrate (2.6mL, 0.044mol) with a weight concentration of 85% were added to 400% ethanol solution, refluxed for 6 hours, stood still, and filtered to obtain intermediate 3, a total of...
Embodiment 6～16
[0135] Preparation of compound Ⅱ-8:
[0136] Intermediates 2-4 were prepared according to steps (1)-(3) in Example 1, except for step (4);
[0137] (4) Synthesis of the target compound 5-(4-benzamidophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (Ⅱ-8)
[0138] Compound 4 (0.58g, 2.5mol) was added to 50mL of anhydrous ethyl acetate solution, stirred at room temperature until the solid was completely dissolved, then 1.5g of triethylamine was added, and benzoyl chloride (2.5 mol) reacted for 6 hours, washed with water, and recrystallized from methanol to obtain 0.25 g of white solid.
[0139] In the 5-(4-substituted arylamide)-1H-pyrazole-3-carboxylic acid ethyl ester compounds of the present invention, Ⅱ-3, Ⅱ-4, Ⅱ-8, Ⅱ-9 to Ⅱ-21 are all according to the above prepared in the same way, only using different acid chlorides in step (4), the acid chlorides are n-butyryl chloride, n-pentanoyl chloride, benzoyl chloride, p-fluorobenzoyl chloride, 2,6-difluorobenzoyl chloride, 2-ch...
Embodiment 17～33
[0141] Synthesis of 5-(4-substituted arylamide)-isoxazole-3-carboxylic acid ethyl ester III compound (Ⅲ-1):
[0142] (1) Synthesis of ethyl 4-(4-nitro)phenyl-2,4-dioxo-butyrate (intermediate 2)
[0143] In a dry reaction flask, add 400 mL of absolute ethanol and 2.3 g of sodium metal to prepare a sodium ethoxide solution. Add 8.3g of p-nitroacetophenone to the sodium ethoxide solution, stir at room temperature until the solid is completely dissolved, then add 15.74g of diethyl oxalate, react for 6 hours, add acetic acid to adjust the pH to 6, and filter with suction to obtain a yellow solid, which is the intermediate Body 2, dried to obtain 11.7g;
[0144] (2) Synthesis of ethyl 5-(4-nitrophenyl)-1H-pyrazole-3-carboxylate (intermediate 31)
[0145] Intermediate 2 (11.7g, 0.044mol) and hydroxylamine hydrochloride (3.1g, 0.044mol) were added to 400mL of absolute ethanol, refluxed for 6 hours, and filtered to obtain intermediate 3' (7.2g);
[0146] (3) Synthesis of ethyl 5-(4-...
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