Arylamine derivative synthesized by deconstructing aza-aromatic hydrocarbon as well as method and application thereof
A technology of azaaromatics and derivatives, applied in the field of pharmaceutical and chemical synthesis, to achieve the effects of safe operation, non-toxic raw materials, and simple synthesis steps
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Embodiment 1
[0075] Add 1 mmol quinoline, 1 mmol benzyl bromide and 1 milliliter of acetone in the flask and stir the reaction for 24 hours at 25° C., filter and wash with ether to obtain the product intermediate N-benzyl quinoline bromide salt; Add 0.25 mmol N-benzylquinoline bromide salt, 0.25 mmol 2-aminobenzyl alcohol, 0.0025 mmol dichlorobis(4-methylisopropylphenyl) ruthenium ( II), 0.125 mmoles of sodium tert-butoxide and 1.5 milliliters of toluene, and stirred and reacted at 130°C for 18 hours, cooled to room temperature after the reaction, diluted the reaction solution, filtered, and evaporated the solvent under reduced pressure to obtain the target product. The chromatographic eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 5:1, and the yield was 78%.
[0076] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows figure 1 and figure 2 As shown, the structural characterization data are as follows:
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Embodiment 2
[0084] After adding 1 mmol of quinoline, 1 mmol of 1-bromo-n-hexane and 1 ml of toluene at 110° C. for 24 hours, the reaction was stirred with diethyl ether to obtain the product intermediate N-hexylquinoline bromide in the flask; Add 0.25 mmol of N-hexylquinoline bromide salt, 0.25 mmol of 2-aminobenzyl alcohol, and 0.0025 mmol of dichlorobis(4-methylisopropylphenyl)ruthenium(II) to the schlenk tube under nitrogen protection. ), 0.125 mmoles of sodium tert-butoxide and 1.5 milliliters of toluene, and stirred and reacted at 130°C for 18 hours, cooled to room temperature after the reaction, diluted the reaction solution, filtered, and evaporated the solvent under reduced pressure to obtain the target product. The eluent was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 5:1, and the yield was 85%.
[0085] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows image 3 and Figure 4 As shown, the struct...
Embodiment 3
[0093] Add 1 mmol quinoline, 1 mmol benzyl bromide and 1 milliliter of acetone in the flask and stir the reaction for 24 hours at 25° C., filter and wash with ether to obtain the product intermediate N-benzyl quinoline bromide salt; Under nitrogen protection, add 0.25 mmol N-benzylquinoline bromide salt, 0.25 mmol 2-amino-3-hydroxymethylpyridine, 0.0025 mmol dichlorobis(4-methylisopropyl Phenyl) ruthenium (II), 0.125 mmoles of sodium tert-butoxide and 1.5 milliliters of toluene, stirred and reacted at 130°C for 18 hours, cooled to room temperature after the reaction, diluted the reaction solution, filtered, and evaporated the solvent under reduced pressure to obtain the target For the product, the column chromatography eluent used was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 3:1, and the yield was 65%.
[0094] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows Figure 5 and Figure 6As shown, the...
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