2-pyrazolyl-5-furyl-1,3,4-oxadiazole derivative as well as preparation method and application thereof
A technology of furyl and pyrazolyl, applied in the field of 2-pyrazolyl-5-furyl-1,3,4-oxadiazole derivatives and its preparation, can solve the problems of drug resistance and achieve good results Insecticidal effect
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Embodiment 1
[0031]
[0032] In a reaction flask, add 5 mmol of intermediate IIa and 30 mL of ethanol, and add 8 mmol of III to it at room temperature. After the addition, the reaction was heated to reflux for 12 hours. Then remove the solvent, dissolve the resulting residue in 50 mL of carbon tetrachloride, add 13 mmol N-bromosuccinimide (NBS) in batches under ice bath conditions, continue to stir in ice bath for 3 hours, and then add triethyl 3 mL of amine was reacted at room temperature for 5 hours. After the reaction is complete, add water to separate the layers, separate the organic phase, and remove the solvent to obtain the crude product and separate it by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 ):δ8.18(s,1H,Pyrazole-H),7.77(d,J=11.6Hz,2H,Ar-H),6.78~7.25(m,4H,Ar-H and Furan-H),4.01( s,3H,CH 3 ).
Embodiment 2
[0034]
[0035] In a reaction flask, add 5 mmol of intermediate IIb and 30 mL of benzene, and add 7 mmol of III to it at room temperature. After the addition, the reaction was heated to reflux for 16 hours. Then the solvent was removed, the resulting residue was dissolved in 35 mL of dichloromethane, 12 mmol N-bromosuccinimide (NBS) was added thereto in batches under ice-bath conditions, stirring was continued for 5 hours in ice-bath, and then triethylamine was added 3 mL, reacted at room temperature for 3 hours. After the reaction is complete, add water to separate the layers, separate the organic phase, and remove the solvent to obtain the crude product to obtain the target compound Ib through column chromatography; 1 H NMR (400MHz, CDCl 3 ):δ8.18(s,1H,Pyrazole-H),7.90(s,1H,Ar-H),7.67(d,J=10.4Hz,1H,Ar-H),7.42(d,J=8.0Hz ,1H,Ar-H),6.81~7.28(m,3H,Ar-Hand Furan-H),4.01(s,3H,CH 3 ).
Embodiment 3
[0037]
[0038] In a reaction flask, add 6 mmol of intermediate IIc and 35 mL of toluene, and add 7 mmol of III to it at room temperature. After the addition, the reaction was heated to reflux for 10 hours. Then the solvent was removed, and the resulting residue was dissolved in 30 mL of chloroform, and 19 mmol N-bromosuccinimide (NBS) was added thereto in batches under ice-bath conditions, and stirring was continued for 2 hours in an ice-bath, and then triethylamine was added. 3 mL, reacted at room temperature for 5 hours. After the reaction is complete, add water to separate the layers, separate the organic phase, and remove the solvent to obtain the crude product, which is separated by column chromatography to obtain the target compound Ic; 1 H NMR (400MHz, CDCl 3 ):δ8.17(s,1H,Pyrazole-H),7.60(d,J=11.6Hz,2H,Ar-H),7.51(d,J=11.2Hz,2H,Ar-H),6.78~7.20 (m,2H,Furan-H),4.01(s,3H,CH 3 ).
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