A method for synthesizing 2,2'-dipolybenzazole compounds

A technology for dipolybenzazole and compound, which is applied in the field of synthesizing 2,2'-dipolybenzazole compounds, can solve the problems of only 35-55% yield, limited sources, low economy, etc. The effect of high economy, wide biological activity and broad application prospects

A technology for dipolybenzazole and compound, which is applied in the field of synthesizing 2,2'-dipolybenzazole compounds, can solve the problems of only 35-55% yield, limited sources, low economy, etc. The effect of high economy, wide biological activity and broad application prospects

CN105622585BInactive Publication Date: 2018-04-03NANJING UNIV OF SCI & TECH
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  • A method for synthesizing 2,2'-dipolybenzazole compounds
  • A method for synthesizing 2,2'-dipolybenzazole compounds
  • A method for synthesizing 2,2'-dipolybenzazole compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Synthesis of 1,1'-bis(pyrimidinyl-2-yl)-1H,1'H-2,2'-diindole

[0038]

[0039] In the reaction vessel, add indole (6mmol, 702.9mg), NaH (mass fraction 60%, 10.8mmol, 432mg), DMF solvent, and react under low temperature for 30 minutes; then add 2-chloropyrimidine (9.6mmol, 1099.488mg ), the mixture was reacted at 100°C for 24 hours, cooled to room temperature, extracted to remove the solvent, and separated by column to obtain compound 1-(pyrimidinyl-2-yl)-1H-indole reactant. Accurately weigh the 1-(pyrimidinyl-2-yl)-1H-indole reactant (0.2mmol, 39.16mg) with an electronic balance, transfer to the reaction vessel, and add AgNO to the reaction vessel 3 (0.20mmol, 33.98mg), Cu(OAc) 2(0.2mmol, 39.90mg), dropwise added toluene solvent into the reaction tube, tightened the stopper of the reaction tube to seal the reaction system, heated to 130°C, and stirred for 16h. After the reaction, the reaction solution was cooled to room temperature, and the solvent was removed unde...

Embodiment 2

[0042] Synthesis of 4,4'-dimethyl-1,1'-bis(pyrimidinyl-2-yl)-1H,1'H-2,2'-diindole.

[0043]

[0044] In the reaction vessel, add 4-methylindole (6mmol, 787.08mg), NaH (mass fraction 60%, 7.2mmol, 288mg), DMF solvent, react at low temperature for 60 minutes; then add 2-chloropyrimidine (6.6 mmol, 755.898 mg), the mixture was reacted at 130°C for 16 hours, cooled to room temperature, extracted to remove the solvent, and separated by column to obtain compound 4-methyl-1-(pyrimidinyl-2-yl)-1H-indole reaction things. Accurately weigh 4-methyl-1-(pyrimidinyl-2-yl)-1H-indole reactant (0.2mmol, 41.85mg) with an electronic balance, transfer to the reaction vessel, add AgNO to the reaction vessel 3 (0.28mmol, 47.57mg), Cu(OAc) 2 (0.3mmol, 59.85mg), dropwise added toluene solvent into the reaction tube, sealed the reaction system, heated to 110°C, and stirred for 24h. After the reaction, the reaction solution was cooled to room temperature, and the solvent was removed under vacuum ...

Embodiment 3

[0047] Synthesis of 4,4'-dibenzyloxy-1,1'-bis(pyrimidinyl-2-yl)-1H,1'H-2,2'-diindole.

[0048]

[0049] In the reaction vessel, add 4-benzyloxyindole (6mmol, 1339.68mg), NaH (mass fraction 60%, 9mmol, 360mg), DMF solvent, react under low temperature condition for 40 minutes; Then add 2-chloropyrimidine (7.2 mmol, 824.616g), the mixture was reacted at 130°C for 24 hours, cooled to room temperature, extracted to remove the solvent, and separated by column to obtain compound 4-benzyloxy-1-(pyrimidinyl-2-yl)-1H-indole Reactant. Accurately weigh 4-benzyloxy-1-(pyrimidinyl-2-yl)-1H-indole reactant (0.2mmol, 60.27mg) with an electronic balance, transfer to the reaction vessel, add AgNO to the reaction vessel 3 (0.24mmol, 40.77mg), Cu(OAc) 2 (0.2mmol, 39.90mg), dropwise added toluene solvent into the reaction tube, sealed the reaction system, heated to 130°C, and stirred for 24h. After the reaction, the reaction solution was cooled to room temperature, and the solvent was remove...

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Abstract

The invention discloses a method for synthesizing 2,2'-dindolylmethane compounds. Firstly, 1-(pyrimidinyl-2-yl)-1H-indole compounds are generated in the mode that indole or substituded indole reacts with 2-chloropyrimidine under the sodium hydride alkaline condition with indole compounds as raw materials, indole guiding groups are introduced into the indole compounds, then the 1-(pyrimidinyl-2-base)-1H-indole compounds are subjected to a dimerization reaction under the action of acetic acid copper, silver nitrate and a toluene solvent, and finally the 2,2'-dindolylmethane compounds are synthesized. A direct carbon activation reaction method is applied, reaction steps are reduced, economical efficiency of reaction is improved, the target product 2,2'-dindolylmethane compounds are efficiently synthesized under the mild condition, indole groups can be removed after the 2,2'-dindolylmethane compounds are de-protected, 2,2'-dindolylmethane is generated, and the structural unit has wide biological activity and application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing 2,2'-dibindole compounds. Background technique [0002] 2,2'-dipolyindole homologues or derivatives are important heterocyclic compounds. The 2,2'-dipolyindole structure exists in many natural bioactive molecules, indigo dyes and Thiel red violet dyes. It can be used to prepare organic electroluminescent materials or certain ion receivers or sensor materials, and is widely used in the fields of material chemistry, medicinal chemistry, dyes and the like. [0003] Conventional methods for synthesizing 2,2'-dipolyindole compounds can be mainly divided into two categories: [0004] One is the ring-forming reaction, which is generally dominated by the ring-forming reaction of N,N'-di-o-tolyloxamide or the ring-forming reaction of o-alkynylaniline compounds. The raw materials for this type of reaction are not easy to obtain, a...

Claims

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Application Information

Patent Timeline
03 Apr 2018
Publication
CN105622585B
IPC
C07D403/14
CPC
C07D403/14
Inventors
姜超; 乐俊