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Preparation method of 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid

A technology of bispyrazolyl biphenyl polycarboxylic acid and carboxyphenylboronic acid, which is applied in two fields, can solve the problems of few reports on pyrazolyl biphenyl carboxylic acid ligands, and achieve the effect of cheap range, economical and efficient reaction

Inactive Publication Date: 2017-05-17
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on pyrazolyl biaryl carboxylic acid ligands.
Nitrogen-containing aromatic carboxylic acid polydentate ligand, nitrogen atom can not only be used as a bridging group, but also can form a stable five- or six-membered chelating ring from N, N, which has not been reported in the literature so far. 2,2´-N , Synthesis of N-bispyrazolyl biphenyl polycarboxylic acid

Method used

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  • Preparation method of 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid
  • Preparation method of 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid
  • Preparation method of 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid

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Experimental program
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Embodiment 1

[0018] 2,2´-N, N-bispyrazolyl biphenyl polycarboxylic acid compound, the general formula is:

[0019]

[0020] The specific structure can be:

[0021]

[0022]

[0023]

[0024]

[0025]

Embodiment 2

[0027] Preparation of 2,2´-N, N-bispyrazolyl biphenyl polycarboxylic acid compound (1): under nitrogen protection, transfer to a 10 ml Schlek reaction tube (a glass commonly used in anhydrous and oxygen-free operation) instrument) by adding 1.0 mmol 2, 5-dibromopyrazine, 2.0 mmol 4-iodopyrazole, 0.01 mmol palladium acetate, 0.02 mmol di-tert-butyl (2',4',6'-triisopropyl-3, 6-dimethoxybiphenyl-2-yl) phosphine, 3.0 mmol sodium tert-butoxide, and 5 ml toluene, replaced the reaction tube with nitrogen for 3 times, then heated to 120 °C with an oil bath under magnetic stirring, and reacted Reflux for 12 hours. Cool down to room temperature; add to the reaction solution, 3.0 mmol 4-carboxyphenylboronic acid, 0.03 mmol palladium acetate, 0.05 mmol 2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate- 1,1'-sodium biphenyl, 6.0 mmol sodium carbonate, and 100 mmol water; then heated to 100° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. Cool dow...

Embodiment 3

[0029] 2, 2´-N, N-bispyrazolyl biphenyl polycarboxylic acid compound (3): under nitrogen protection, transfer to a 10 ml Schlek reaction tube (a glass commonly used in anhydrous and oxygen-free operation) instrument) by adding 1.0 mmol 2,5-dibromopyrazine, 2.1 mmol 4-iodopyrazole, 0.02 mmol palladium acetate, 0.03 mmol dicyclohexyl (3,6-dimethoxy-2',4',6' -triisopropyl(1,1'-biphenyl)-2-yl)phosphine, 3.0 mmol potassium tert-butoxide, and 5 ml dioxane, replace the reaction tube with nitrogen three times, and then use The oil bath was heated to 110°C and the reaction was refluxed for 18 hours. Cool down to room temperature; then add 5.0 mmol 3,5-dicarboxyphenylboronic acid, 0.03 mmol palladium acetate, 0.05 mmol 2'-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1 , 1'-biphenyl sodium salt, 12.0 mmol cesium carbonate, and 200 mmol water; then heated to 110° C. in an oil bath under magnetic stirring, and the reaction was refluxed for 36 hours. Cool down to room temperature; add 20ml ...

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Abstract

The invention relates to a preparation method of a 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid compound. The preparation method comprises the following steps: adding 4-halogeno pyrazol, a bis-2-halogeno N heterocyclic compound, palladium salt, a phosphorus ligand and alkali in an organic solvent; heating under the protection of N2 gas; cooling to room temperature after the end of a reaction; then adding carboxyphenylboronic acid, the palladium salt, the phosphorus ligand, the alkali and water; after the end of a reaction, adding water, filtering, acidifying, and filtering and drying an obtained solid, thus obtaining the 2,2'-N,N-bis-pyrazolyl biphenyl polycarboxylic acid compound. The convenient and practical preparation method is provided for synthesizing a 2,2'-N,N-biphenyl polycarboxylic acid compound ligand by utilizing a palladium metal catalyst which is commercially available, and performing one-pot catalysis on a carbon-nitrogen coupling reaction of the 4-halogeno pyrazol and the bis-2-halogeno N heterocyclic compound and a carbon-carbon coupling reaction of the carboxyphenylboronic acid. According to the preparation method disclosed by the invention, the raw materials are commercially available, reaction substrates are cheap, the range is wide, the reaction is economic and efficient, and the application value is important.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2,2´-N, N-bispyrazolyl biphenyl polycarboxylic acid. Background technique [0002] In recent years, metal-organic frameworks (MOFs) have attracted extensive attention from chemists due to their unique properties. They have potential applications in supramolecular chemistry, crystal engineering, materials, gas storage, chemical sensing, catalysis, etc. Among various factors affecting the structure of metal-organic framework compounds, the structure of the ligand is the most important factor. Among them, aromatic polycarboxylic acid ligands have a rigid structure, multiple coordination sites, diverse coordination modes, and rich weak interactions between solvent molecules, which occupy an important position in metal-organic frameworks (MOFs). In recent years, nitrogen-containing heterocyclic polydentate carboxylic acid ligands and their complexes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14
CPCC07D401/14C07D403/14
Inventor 李红梅徐晨王志强涂田勇郝新奇
Owner LUOYANG NORMAL UNIV
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