Synthesis of oxadiazole derivatives and application of oxadiazole derivatives in field of antibacterial drugs
A technology of antibacterial drugs and derivatives, applied in antibacterial drugs, organic chemistry, etc.
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Embodiment 1
[0020] Example 1: 2-(4-fluorophenyl)-5-((2-methyl-5-nitro-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole ( Compound 1) Preparation
[0021]
[0022] React dimethylpentanitroimidazole with ethyl chloroacetate, the dosage is 5 mmol of dimethyl pentanitroimidazole, 5 mmol of ethyl chloroacetate, add 5 mmol of potassium carbonate as a catalyst, and add an appropriate amount of acetone as a solvent to dissolve in In a 50mL round bottom flask, react at 50-60°C; track the reaction with thin layer chromatography (TLC), heat to reflux until the reaction is complete; Purified by crystallization to obtain ethyl nitroimidazole acetate. Dissolve the solid obtained in the previous step in methanol and react with hydrazine hydrate. The dosage is nitroimidazole ethyl acetate (1 mmol) and hydrazine hydrate (6 mmol). Stir and heat to 70°C. After 4 hours of reaction, put it in a -20°C refrigerator to cool overnight, and the next day, the precipitated solid was filtered and washed with water to o...
Embodiment 2
[0023] Example 2: 2-(4-fluorophenyl)-5-((2-methyl-5-nitro-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole ( Compound 2) Preparation
[0024]
[0025] The preparation method is the same as in Example 1. Substitute p-chlorophenylacetic acid for p-fluorophenylacetic acid to obtain the target compound. Yield 67%, mp: 255-256°C. 1 H NMR (300MHz, DMSO-d 6 )δ: 2.23(s, 3H), 3.56(s, 2H), 4.84(s, 2H), 7.23-7.36(m, 4H), 8.28(s, 1H). MS(E SI): 334.73(C 14 h 13 ClN 5 o 3 ,[M+H] + ).Anal.Calcd for C 14 h 12 ClN 5 o 3 : C, 50.39; H, 3.62; N, 20.99. Found: C, 50.36; H, 3.64; N, 20.96.
Embodiment 3
[0026] Example three: 2-(4-bromophenyl)-5-((2-methyl-5-nitro-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole ( Compound 3) Preparation
[0027]
[0028] The preparation method is the same as in Example 1. Substitute p-bromophenylacetic acid for p-fluorophenylacetic acid to obtain the target compound. Yield 61%, mp: 225-227°C. 1 H NMR (300MHz, DMSO-d 6 )δ: 2.27(s, 3H), 3.46(s, 2H), 4.91(s, 2H), 7.17-7.30(m, 2H), 7.51(t, J=9.24Hz, 2H) 8.33(t, J= 9.60Hz, 1H). MS (ESI): 379.18 (C 14 h 13 BrN 5 o 3 ,[M+H] + ).Anal.Calcd for C 14 h 12 BrN 5 o 3 : C, 44.46; H, 3.20; N, 18.52. Found: C, 44.48; H, 3.21; N, 18.50.
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