Quinazine-type azabiaryl-ring axial chiral compound and its synthesis method
A synthesis method and azabis technology are applied in the field of quinazine-type azabi-aromatic ring-axial chiral compounds and their synthesis, which can solve the problems of poor functional group compatibility, severe conditions and the like, and achieve mild reaction conditions, good compatibility, Atomic economy good effect
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Embodiment 1
[0049] R is OEt, and the molecular structure of the quinolizine azabiaromatic chiral compound is:
[0050]
[0051]Under the atmosphere of argon protection, 1-ethynyl-2-ethoxynaphthalene was dissolved in tetrahydrofuran solution, the reaction system was lowered to -78±5°C, and then lithium diisopropylamide solution was added; the system was in the same After reacting for 1±0.1 h at the temperature, methyl chloroformate was then added, the reaction was continued at the same temperature, and 10 minutes later, saturated ammonium chloride solution was added for extraction. The reaction solution was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was spin-dried and purified by column chromatography to obtain Intermediate 1. The tetrahydrofuran solution of 2-picoline was cooled to -78±5°C, then the lithium diisopropylamide solution was added, the system was reacted at the same temper...
Embodiment 2
[0054] R is NBn 2 , the molecular structure of quinolizine azabiaromatic chiral compounds is:
[0055]
[0056] Under the atmosphere of argon protection, 1-ethynyl-2-bisbenzylaminonaphthalene was dissolved in tetrahydrofuran solution, the reaction system was lowered to -78±5℃, and then lithium diisopropylamide solution was added; the system was in the same After reacting for 1±0.1 h at the temperature, methyl chloroformate was then added, the reaction was continued at the same temperature, and 10 minutes later, saturated ammonium chloride solution was added for extraction. The reaction solution was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was spin-dried and purified by column chromatography. Intermediate 1 is obtained. The tetrahydrofuran solution of 2-picoline was cooled to -78±5°C, then the lithium diisopropylamide solution was added, the system was reacted at the sa...
Embodiment 3
[0059] R is Me, and the molecular structure of the quinolizine azabiaromatic chiral compound is:
[0060]
[0061] Under the atmosphere of argon protection, 1-ethynyl-2-methylnaphthalene was dissolved in tetrahydrofuran solution, the reaction system was lowered to -78±5℃, and then lithium diisopropylamide solution was added; the system was at the same temperature After reacting for 1±0.1 h, methyl chloroformate was then added, the reaction was continued at the same temperature, and 10 minutes later, saturated ammonium chloride solution was added for extraction. The reaction solution was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was spin-dried and purified by column chromatography. Intermediate 1 is obtained. The tetrahydrofuran solution of 2-picoline was cooled to -78±5°C, then the lithium diisopropylamide solution was added, the system was reacted at the same temperatur...
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