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Chiral and non-chiral diimidazolinylbenzene compounds and synthesis method

A technology for bisimidazolinylbenzene and compound, which is applied in the field of chiral and achiral bisimidazolinylbenzene compounds and synthesis, can solve the problems of limited application, difficult preparation of chiral diamine and high price, and achieves good application Foreground effect

Inactive Publication Date: 2007-08-08
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Among the many imidazoline compounds synthesized, most of them are achiral compounds, while the research on chiral imidazoline compounds is less, and there are only a few cases of chiral bis-imidazoline compounds (such as 2,6-bis-imidazoline compounds). Pyridine (Org.Lett.2005, 7, 3393, bis-imidazolinyl alkane (Org.Biomol.Chem.2004, 2, 1995); in addition, in the research on the synthesis method of imidazoline compounds, it is mainly the reaction of acid or ester with diamine The synthesis method of dehydration and ring closure limits the application of this method in the synthesis of chiral imidazolines due to the difficulty and high price of chiral diamines.

Method used

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  • Chiral and non-chiral diimidazolinylbenzene compounds and synthesis method
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Examples

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example 1

[0017] Example 1, the preparation of 1,3-bis(4,5-dihydro-1-p-tolyl-1H-imidazol-2-yl)benzene: N,N'-bis(2-hydroxyethyl)-1, A solution of 3-dibenzamide (2.4 mmol) in thionyl chloride (3 mL, 41.3 mmol) was stirred under reflux for 4 hours, and the excess thionyl chloride was removed by rotary evaporation to obtain a pale yellow oil, which was dissolved in dry ether ( 10 mL), filtered to remove insoluble matter, added dry triethylamine (2 mL, 14.3 mmol), then added p-toluidine (565 mg, 5.28 mmol), and stirred the reaction solution at room temperature for 5 hours. After the reaction, add 20 mL of 10% NaOH aqueous solution, extract with dichloromethane (3 times, 20 mL each time), combine the organic phases, wash with saturated brine, anhydrous MgSO 4 After drying, the solvent was evaporated under vacuum, and methanol was used as developing solvent to separate the pure product with a yield of 68.5%. M.p.: 169-170℃, IR(KBr): v3030, 2923, 2866, 1618, 1587, 1513, 1486, 1420, 1383, 1322,...

example 2

[0018] Example 2, the preparation of 1,3-bis((S)-4-isopropyl-4,5-dihydro-1-p-tolyl-1H-imidazol-2-yl)benzene: N,N'-bis A solution of ((S)-1-hydroxy-3-methylbutyl-2-yl)-1,3-dibenzamide (2.4 mmol) in thionyl chloride (3 mL, 41.3 mmol) was stirred at reflux for 6 hours, The excess thionyl chloride was rotary evaporated to obtain a pale yellow oil, which was dissolved in dry diethyl ether (10 mL), filtered to remove insoluble matter, and dried triethylamine (2 mL, 14.3 mmol) was added, followed by p-toluidine (565 mg, 5.28 mmol), and the reaction solution was stirred at room temperature for 6 hours. After the reaction, 20 mL of 10% NaOH aqueous solution was added, extracted with dichloromethane (3 times, 20 mL each time), the organic phases were combined, washed with saturated brine, anhydrous MgSO 4 After drying, the solvent was evaporated under vacuum, and acetone was used as a developing agent to separate the product with a yield of 44.5%. Pale yellow oil, IR (KBr): v 3032, 29...

example 3

[0019] Example 3, the preparation of 1,3-bis((S)-4-benzyl-4,5-dihydro-1-p-tolyl-1H-imidazol-2-yl)benzene: N,N'-bis( (S)-1-hydroxy-3-phenylpropyl-2-yl)-1,3-dibenzamide (2.4mmol) in thionyl chloride (3mL, 41.3mmol) was stirred under reflux for 8 hours, and The excess thionyl chloride was distilled off to obtain a pale yellow oil, which was dissolved in dry diethyl ether (10 mL), filtered to remove insoluble matter, and dried triethylamine (2 mL, 14.3 mmol) was added, followed by p-toluidine ( 565mg, 5.28mmol), and the reaction solution was stirred at room temperature for 7 hours. After the reaction, 20 mL of 10% NaOH aqueous solution was added, extracted with dichloromethane (3 times, 20 mL each time), the organic phases were combined, washed with saturated brine, anhydrous MgSO 4 After drying, the solvent was evaporated under vacuum, and acetone was used as a developing agent to separate the product with a yield of 53.7%. Pale yellow oil, IR (KBr): v3060, 3027, 2922, 2867, 16...

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Abstract

The invention discloses a chirality and non-chirality diimidazoline benzene compound and synthesizing method with general formula as right formula (R1 is H, i-Pr or Bn; R2 is p-phenylmethyl, p-tolyloxy, cyclohexyl or isopropyl; R3 is H, OH, NO2, NH2 or CH3COO), which comprises the following steps: refluxing bishydralkamine in the thionyl chloride; evaporating excessive thionyl chloride; dissolving in the ether; filtering; adding trimethylamine and different substituted ammonia; stirring under indoor temperature; adding sodium hydroxide solution; extracting; drying; condensing; proceeding film chromatographic separation; obtaining the product.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and relates to chiral and achiral bis-imidazolinyl benzene compounds and a synthesis method. Background technique [0002] Asymmetric catalytic technology has achieved great success in both basic research and applied research, especially in the past ten years since the 1990s, new structural ligands, new asymmetric The concepts and methods of asymmetric catalysis emerge in endlessly, and the research on asymmetric catalysis is in an unprecedented stage of prosperity. [0003] Among the many monodentate, bidentate and polydentate chiral ligands with P, N, O and other coordinating atoms, bisoxazoline is one of the most attractive ligand types. This kind of ligand is easy to prepare, chiral The source is easy to obtain and the structure is adjustable, mainly from the amidation, halogenation and basic ring closure of chiral amino alcohols. The bisoxazoline liga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
Inventor 宋毛平龚军芳郝新奇武利园汪亚男吴养洁
Owner ZHENGZHOU UNIV
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