Preparation method and application of open-ring nitromethylene derivative
A technology based on alkyl and phenyl, applied in the field of preparation of ring-opening nitromethylene derivatives, can solve the problems of restricting the development of compounds, limiting the selectivity of pesticides for pest control, light instability and low LogP value, etc.
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[0079] The preparation method of the compound of the present invention
[0080] The compound of formula I of the present invention can be prepared by the following method, but the conditions of the method, such as reactants, solvents, bases, the amount of the compound used, reaction temperature, time required for reaction, etc. are not limited to the following explanations. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.
[0081] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at -20°C to reflux temperature (preferably preferably -10°C to 80°C, more preferably 0°C to 50°C). The reaction time is usually 0.1 hour to 24 hours, preferably 0.5 to 12 hours, more preferably 1 to 5 hours. ...
Embodiment 1
[0092] 6-(((6-chloropyridin-3-yl)methyl)(ethyl)amine)-1-methyl-5-nitro-1,2,3,4-tetrahydropyridin-2-ol ( Compound 1) Synthesis:
[0093] (1) Synthesis of 1,1-dimethylthio-2-nitroethylene:
[0094]
[0095] In a 500mL three-neck round bottom flask equipped with a thermometer and a constant pressure dropping funnel, add nitromethane (20g, 0.325mol), absolute ethanol (50mL) and carbon disulfide (30mL, 0.500mol), Add potassium hydroxide (40g, 0.710mol) in dehydrated ethanol (200mL) solution, control the drop rate of potassium hydroxide alcoholic solution to make the reaction temperature between 30-35°C, continue to stir the reaction at room temperature after the dropwise addition After 30 min, suction filtration, the filter cake was washed successively with 50 mL of absolute ethanol and 50 mL of absolute ether, and vacuum-dried to obtain 48.5 g of a brown solid with a yield of 69%, which was used for the next step of synthesis without purification.
[0096] In a 250 ml three-n...
Embodiment 2
[0110] N-((6-chloropyridin-3-yl)methyl)-1-methyl-3-nitro-6-propoxy-1,4,5,6-tetrahydropyridin-2-amine (compound 14) Synthesis:
[0111]
[0112] Add N-((6-chloropyridin-3-yl)methyl)-N-methyl-2-nitrovinylidene-1,1-diamine (0.80g, 3.3 mmol), acrolein (0.68mL, 11mmol, ρ=0.9g / mL), propenyl alcohol (1.07g, 18mmol), dichloromethane (15ml), a catalytic amount of boron trifluoride ether solution was added dropwise, and the temperature was raised to reflux State, TLC tracks the reaction process, and the reaction time is about two hours. After the reaction, the dichloromethane solvent is rotated to obtain a red slurry, and then an appropriate amount of dichloromethane is added to it, with silica gel as a filler, PE:EA= 1:2, dichloromethane: acetone = 5:1 was used as the developer gradient for column separation, the product was collected, and then precipitated with ether to obtain 119 mg of a yellow solid with a yield of 35%. Mp: 80.1-84.2°C. 1 H NMR (CDCl 3 , 500MHz): δ (ppm) 8.30...
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