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Preparation method of phosphonyl-containing isoxazole

A technology of phosphonoisoxazole and acyl nitrile oxide is applied in the field of preparation of isoxazole and achieves the effects of mild conditions and easy operation

Pending Publication Date: 2020-07-24
TIANJIN AGRICULTURE COLLEGE
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Problems solved by technology

Accordingly, the synthesis of 5-phosphonoisoxazole requires the use of alkynyl phosphonate, and the most commonly used method for preparing 1-alkynyl phosphonate is to react with chlorophosphate by alkyne Grignard reagent or lithium reagent, and This traditional method has too many restrictions on the functional groups of the reactants, and requires anhydrous and oxygen-free operation (Eur.J.Org.Chem.2000, 3103~3115)

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  • Preparation method of phosphonyl-containing isoxazole

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Embodiment

[0008] 1) Synthesis of Phosphonoisoxazoline II

[0009] Add 0.44g (2.0mmol) of diethyl α-acetoxyvinylphosphonate and 1.1g (2.2mmol) of ammonium cerium nitrate into a 25mL round bottom bottle, add 10mL of anhydrous acetone or acetophenone, and heat to reflux under electromagnetic stirring After 10 h, the solvent was distilled off under reduced pressure to obtain a light yellow viscous substance. Column chromatography, eluent ethyl acetate / petroleum ether=1 / 1, gave the phosphonoisoxazoline II product, and its data is as follows: IIa( R is phenyl): 31 P NMR (CDCl3): δ=10.29ppm; 1 H NMR (CDCl3): δ=8.21-8.24 (m, 2H), 7.60-7.65 (m, 1H), 7.46-7.52 (m, 2H), 4.31-4.40 (m, 4H), 3.86 (m, 2H) , 2.17(s, 3H), 1.39(t, J=7.2Hz, 6H);

[0010] Anal.Calcd.for C 16 h 20 NO 7 P: C, 52.04; H, 5.46; N, 3.79. Found: C, 51.90; H, 5.61; N, 3.61.

[0011] IIb (R is methyl): 31 P NMR (CDCl 3 ): δ=10.20ppm; 1 H NMR (CDCl 3 ): δ=4.28-4.35(m, 4H), 3.61(m, 2H), 2.55(s, 3H, COCH 3 ), 2.15(s, 3H, O...

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Abstract

The invention discloses a preparation method of isoxazole containing phosphonyl. According to the preparation method, alpha-acetoxyl vinyl diethyl phosphonate and acyl nitrile oxide react to synthesize 5-phosphonyl isoxazoline, then an elimination reaction is carried out under acid catalysis, and 5-phosphonyl isoxazole can be almost quantitatively obtained. The method is mild in condition and simple and convenient to operate, and has a certain application value.

Description

technical field [0001] The invention relates to a preparation method of isoxazole, in particular to a preparation method of phosphono-containing isoxazole. Background technique [0002] Isoxazole is a very important heterocyclic compound. Due to its physiological and biological activities such as bactericidal, anticancer, antiviral, anti-inflammatory and herbicidal, it has attracted much attention in recent years. 1,3-dipolar cycloaddition is a classic reaction for the synthesis of five-membered heterocyclic compounds in chemical reactions. The process of cycloaddition reaction between five-membered heterocyclic compounds. Among them, the 1,3-dipolar cycloaddition of alkynes and nitrile oxides is the most direct way to obtain isoxazole heterocycles. Accordingly, the synthesis of 5-phosphonoisoxazole requires the use of alkynyl phosphonate, and the most commonly used method for preparing 1-alkynyl phosphonate is to react with chlorophosphate by alkyne Grignard reagent or li...

Claims

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Application Information

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IPC IPC(8): C07F9/653
CPCC07F9/653
Inventor 吕丽娟葛畅尚志强
Owner TIANJIN AGRICULTURE COLLEGE
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