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Synthetic method of fused cyclic ketone type compound

A synthesis method and compound technology, applied in the synthesis of fused ring compounds and fused ring ketone compounds, can solve the problems of low oxidation state of C-H bond, difficult chemoselective regioselectivity, difficult C-O bond, etc.

Inactive Publication Date: 2015-11-04
广州市泊美化妆品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But on the other hand, in modern synthetic chemistry technology, direct construction of C-O bonds is a very challenging topic in the field of organic synthesis, because the low oxidation state, chemoselectivity and regioselectivity of C-H bonds in organic molecules are difficult to control, making it difficult to form C-O bonds directly

Method used

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  • Synthetic method of fused cyclic ketone type compound
  • Synthetic method of fused cyclic ketone type compound
  • Synthetic method of fused cyclic ketone type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] At room temperature, to a mixed solvent of 1-n-butyl-2,3-dimethylimidazolium tetrafluoroborate and polyethylene glycol-200 (PEG-200) with a volume ratio of 1:8, add 100mmol formula (I) compound, 140mmol formula (II) compound, 4mmol catalyst Pd (TFA) 2 , 10mmol catalytic promoter diethyldiselenide and 7mmol composite activator (being the mixture of 2mmol N-fluorobisbenzenesulfonamide (NFSI) and 5mmol boron trifluoride ether), then warming up to 50°C, and in the Reaction at high temperature for 3 hours, then add 100mmol base diisopropylethanolamine to the reaction system, and continue to keep warm for 3 hours at this temperature;

[0038]After the reaction is completed, filter while it is hot, adjust the pH value of the filtrate to be neutral, then fully wash 2-3 times with saturated aqueous sodium bicarbonate solution, separate the organic phase, concentrate under reduced pressure, and pass the residue through 200-300 mesh silica gel column chromatography. A...

Embodiment 2

[0042]

[0043] At room temperature, to a mixed solvent of 1-n-butyl-2,3-dimethylimidazolium tetrafluoroborate and polyethylene glycol-200 (PEG-200) with a volume ratio of 1:8, add 100mmol formula (I) compound, 170mmol formula (II) compound, 7mmol catalyst Pd (TFA) 2 , 15mmol catalytic promoter diethyldiselenide and 12mmol composite activator (a mixture of 4mmol N-fluorobisbenzenesulfonamide (NFSI) and 8mmol boron trifluoride ether), then warming up to 70°C, and in the Reaction at high temperature for 2 hours, then add 120mmol base diisopropylethanolamine to the reaction system, and continue to keep warm for 4 hours at this temperature;

[0044] After the reaction is completed, filter while it is hot, adjust the pH value of the filtrate to be neutral, then fully wash 2-3 times with saturated aqueous sodium bicarbonate solution, separate the organic phase, concentrate under reduced pressure, and pass the residue through 200-300 mesh silica gel column chromatography. A mixed...

Embodiment 3

[0048]

[0049] At room temperature, to a mixed solvent of 1-n-butyl-2,3-dimethylimidazolium tetrafluoroborate and polyethylene glycol-200 (PEG-200) with a volume ratio of 1:8, add 100mmol formula (I) compound, 200mmol formula (II) compound, 5mmol catalyst Pd (TFA) 2 , 20mmol catalytic promoter diethyldiselenide and 15mmol composite activator (a mixture of 3.75mmol N-fluorobisbenzenesulfonamide (NFSI) and 11.25mmol boron trifluoride ether), then warming up to 80°C, and React at this temperature for 2.5 hours, then add 150mmol base diisopropylethanolamine to the reaction system, and continue the insulation reaction at this temperature for 5 hours;

[0050] After the reaction is completed, filter while it is hot, adjust the pH value of the filtrate to be neutral, then fully wash 2-3 times with saturated aqueous sodium bicarbonate solution, separate the organic phase, concentrate under reduced pressure, and pass the residue through 200-300 mesh silica gel column chromatography...

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Abstract

The invention relates to a synthetic method of a fused cyclic ketone type compound which is shown as the following formula (III) (as shown in the description). The method comprises the following steps of: in a solvent, in the presence of a catalyst, a catalytic promotor and a composite activating agent, enabling a compound in the following formula (I) and a compound in the following formula (II) to perform a reaction for 2-3 hours at the temperature of 50-80 DEG C, then adding alkali, and continuing the reaction for 3-5 hours so as to obtain the compound in the formula (III), wherein R1 and R2 are respectively and independently selected from H, halogen, C1-C6 alkyl or C1-C6 alkoxy groups; X is halogen. According to the method, specific kinds and components of the catalyst, the catalytic promotor, the composite activating agent, the alkali, the solvent and the like are selected, and an appropriate alkali adding opportunity is selected, so that unique synergistic action is exerted among the catalyst, the catalytic promotor, the composite activating agent, the alkali, the solvent, and the like, target products in a high yield can be obtained, and the method has favorable application prospects and broad industrialized production potential in the field of organic synthesis, and particularly in the technical field of intermediate synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing fused ring compounds, more particularly to a method for synthesizing fused ring ketone compounds, and belongs to the field of organic intermediate synthesis. Background technique [0002] Fused ring ketones have important functions and uses in organic synthesis, especially in the technical field of pharmaceutical intermediate synthesis. Because they contain fused rings and carbonyl groups that are prone to further reactions, they are often used to construct synthetic drugs, Common structural fragments of natural product and material molecules. It is precisely because of the important potential of this type of structural compounds that the development of new and efficient synthetic methods for fused cyclic ketones has increasingly become a key issue in scientific research. [0003] But on the other hand, in modern synthetic chemistry technology, direct construction of C-O bonds is a very challenging to...

Claims

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Application Information

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IPC IPC(8): C07D307/83
CPCC07D307/83
Inventor 朱勇
Owner 广州市泊美化妆品有限公司