Synthetic method of diaryl oxazepine compounds
A synthesis method and a technology for heterodroxone, applied in the field of organic synthesis, can solve the problems of limited application and high amount of palladium catalyst, and achieve the effects of simple operation, high yield and economical efficiency
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Embodiment 1
[0028] Preparation of diaryloxazepine compounds (1): Add 1.0mmol o-hydroxyarylmethanol, 1.5mmol o-bromoaniline, 0.01mmol p-cymene dichloride to a 10 ml flask in an air atmosphere Ruthenium dimer, 0.03mmol cuprous iodide, 0.05mmol 2,2'-bis(dicyclohexylphosphine)-1,1'-binaphthyl, 3.0mmol potassium hydroxide, and 5ml toluene, then put on the rack The condenser tube was heated to 100° C. with an oil bath under magnetic stirring, and reacted for 10 hours. Remove the oil bath, add 3ml of water to the reaction solution, extract three times with 5ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain pure product 1 with a yield of 88%. The nuclear magnetic analysis data of this product are as follows: 1 HNMR: 10.53 (s, 1H), 7.76 (d, 1H), 7.59 (d, 1H), 7.33-7.28 (m, 3H), 7.11-7.09 (m, 3...
Embodiment 2
[0030] Preparation of diaryloxazepine compounds (3): Add 1.0mmol 4-methyl-2-hydroxyarylmethanol, 1.5mmol o-iodoaniline, 0.03mmol p-cymene dichloride ruthenium dimer, 0.05 mmol cuprous bromide, 0.05 mmol 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, 3.0 mmol sodium tert-butoxide, and 5ml of dioxane, and then put a cooling tube on the rack and heat to 80°C with an oil bath under magnetic stirring, and react for 24 hours. Remove the oil bath, add 3ml of water to the reaction solution, extract three times with 5ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain pure product 3 with a yield of 90%. The nuclear magnetic analysis data of this product are as follows: The nuclear magnetic analysis data of this product are as follows: 1 HNMR: 10.45 (s, 1H), 7.74 (d, 1H), 7.58 (d, 1H),...
Embodiment 3
[0032] Preparation of diaryloxazepinones (6): In air atmosphere, add 1.0mmol o-hydroxyarylmethanol, 1.3mmol 4-trifluoromethyl-2-bromoaniline, 0.05 mmol p-cymene dichloride ruthenium dimer, 0.1 mmol cuprous chloride, 0.1 mmol 1,1'-bis(diphenylphosphino)ferrocene, 9.0 mmol potassium tert-butoxide, and 5 ml xylene , and then put a cooling tube on the rack and heat to 120° C. with an oil bath under magnetic stirring, and react for 12 hours. Remove the oil bath, add 3ml of water to the reaction solution, extract three times with 5ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain pure product 6 with a yield of 87%. The nuclear magnetic analysis data of this product are as follows: 1 HNMR: 10.72 (s, 1H), 7.78 (d, 1H), 7.63 (d, 1H), 7.55-7.48 (m, 3H), 7.38 (d, 1H), 7.33 (t, 1H). ...
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