Diaryl-azepin-5-one compound synthesis method

A ketone compound and a synthesis method technology, applied in the field of organic synthesis, can solve the problems of cumbersome preparation, large environmental pollution, hard-to-obtain species and the like, and achieve the effects of economical and efficient reaction, low environmental pollution, and wide range of cheapness

Inactive Publication Date: 2015-09-16
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] These palladium-catalyzed synthetic methods need to use special substrates, which are not easy to obtain and have limited types. to a certain limit

Method used

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  • Diaryl-azepin-5-one compound synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of biaryl azepin-5-ones compound (1): Under nitrogen protection, add 1.0mmol o-bromobenzyl alcohol, 2.0mmol benzonitrile, 0.02mmol RuH 2 (PPh 3 ) 4 , 0.03mmol palladium acetate, 0.05mmol 1,3-bis(2,6-diisopropylphenyl)imidazole chloride, 2.0mmol sodium hydride, and 5ml toluene, replace the reaction tube with nitrogen for 3 times, and then stir the Heated to 110°C with an oil bath, and the reaction was refluxed for 24 hours. Remove the oil bath and lower to room temperature; add 3ml of water to the reaction solution, extract three times with 5ml of dichloromethane, 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 , 85% yield. The nuclear magnetic analysis data of this product are as follows: 1 H NMR. (400 MHz, CDCl 3 ): δ 8.01 (d, 1H), 7.69–7.56 (m, 3H), 7....

Embodiment 2

[0038] Preparation of biaryl azepin-5-ones compound (3): Under nitrogen protection, add 1.0mmol benzyl alcohol, 1.2mmol 2-bromo-5-chlorobenzonitrile, 0.1mmol RuH 2 (CO)(PPh 3 ) 3 , 0.1 mmol palladium chloride, 0.15 mmol 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate, 3.0 mmol sodium tert-butoxide, and 5 ml benzene, The reaction tube was replaced with nitrogen for 3 times, then heated to 100° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 6 hours. Remove the oil bath and lower to room temperature; add 3ml of water to the reaction solution, extract three times with 5ml of dichloromethane, 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 2 , yield 82%. The nuclear magnetic analysis data of this product are as follows: 1 H NMR...

Embodiment 3

[0040] Preparation of biaryl azepin-5-ones (6): Under the protection of nitrogen, add 1.0mmol benzyl alcohol, 1.1mmol 2-bromo-4-methoxybenzonitrile, 0.05mmol RuH 2 (CO)(PPh 3 ) 3 ,, 0.06 mmol of palladium acetate, 0.1 mmol of 1,3-bis(2,6-diisopropylphenyl) imidazole bromide, 6.0 mmol of potassium tert-butoxide, and 5 ml of dioxane, and replace reaction tube 3 with nitrogen gas times, and then heated to 110°C with an oil bath under magnetic stirring, and the reaction was refluxed for 10 hours. Remove the oil bath and lower to room temperature; add 3ml of water to the reaction solution, extract three times with 5ml of dichloromethane, 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 , 80% yield. The nuclear magnetic analysis data of this product are as follows: 1 H NMR. (400 M...

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Abstract

The invention relates to a diaryl-azepin-5-one compound synthesis method. The method comprises that o-haloarylmethanol and aryl cyanide (or a mixture of aryl methanol and o-haloarylmethanol), a ruthenium catalyst, a palladium salt, azacycloimidazolium salt and an alkali are added into an organic solvent and the solution is heated in a N2 protective atmosphere so that through a hydrogen transfer reaction and a carbon-hydrogen bond activation reaction, the diaryl-azepin-5-one compound is produced. The method provides an economic and practical preparation method for synthesis of the substituted diaryl-azepin-5-one derivative with drug activity. The method has simple processes, utilizes cheap reaction substrates with a wide source scope, produces small environment pollution, has high reaction economy and efficiency and has an important application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing biarylazepine-5-one compounds. Background technique [0002] The basic structural unit of azepines is a seven-membered azepine ring containing a nitrogen atom. Aryl azepines are heterocyclic compounds with unique physiological and pharmacological activities, which have attracted people's attention. Some of these compounds have antipsychotic, analgesic and therapeutic effects on cardiovascular diseases, etc., which have great medicinal potential and broad application prospects. Although many types of aryl azepines have been synthesized, few biaryl azepines-5-ones have been reported. In 1991, Grigg et al. reported that palladium catalyzed the internal reaction of dihaloarenes with amide groups as special substrates to synthesize biaryl azepine-5-ones (Tetrahedron Letters, 1991, 32, 3859-3862) . [0003] ; [0004] In 2010, Goh et al. report...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/18
CPCC07D223/18
Inventor 李红梅徐晨祖恩普王志强付维军
Owner LUOYANG NORMAL UNIV
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