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Preparation method for synthesizing polysubstituted cyclic 1,2-diketone by sulfoxide participating in arylation

A multi-substitution and chemical synthesis technology, applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of expensive transition metals, high reaction temperature, etc., and achieve the effect of eliminating metal residues, wide substrate range, and high yield

Active Publication Date: 2019-09-20
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although effective, these stepwise approaches often require the use of expensive transition metals and high reaction temperatures

Method used

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  • Preparation method for synthesizing polysubstituted cyclic 1,2-diketone by sulfoxide participating in arylation
  • Preparation method for synthesizing polysubstituted cyclic 1,2-diketone by sulfoxide participating in arylation
  • Preparation method for synthesizing polysubstituted cyclic 1,2-diketone by sulfoxide participating in arylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] To a 20mL test tube, add phenylthiophene sulfoxide (21mg, 0.1mmol) and 3-methylcyclopentane-1,2dione (17.1mg, 0.15mmol) successively at room temperature, and add 0.8ml of dichloro Ethane, placed in a low-temperature reactor at -10°C, wait for the reaction system to mix evenly and the reactant body will be -10°C, add trifluoroacetic anhydride (21mg, 0.15mmol), and react at a low temperature of -10°C for 4h, then The reaction mixture was allowed to warm to room temperature (typically 25°C) and stirred at this temperature for 1 min. After completion, the reaction system in the test tube was transferred to a 10ml eggplant-shaped bottle without any post-processing operation. Using a Heidolph rotary evaporator, the rotation speed was 80-100rpm, the temperature was 38°C, and the vacuum degree was 0.1Mpa. The residue was subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether:ethyl acetate=9:1, and th...

Embodiment 2

[0041]

[0042] To a 20mL test tube, diphenylsulfoxide (20.6mg, 0.1mmol) and 3-methylcyclopentane-1,2dione (17.1mg, 0.15mmol) were added sequentially at room temperature, and 0.8ml di Ethyl chloride, placed in a low-temperature reactor at -10°C, wait for the reaction system to mix evenly and the reaction body will be -10°C, add trifluoroacetic anhydride (21mg, 0.15mmol), and react at a low temperature of -10°C for 4h, The reaction mixture was then allowed to warm to room temperature (typically 25°C) and stirred at this temperature for 1 min. After completion, the reaction system in the test tube was transferred to a 10ml eggplant-shaped bottle without any post-processing operation. Using a Heidolph rotary evaporator, the rotation speed was 80-100rpm, the temperature was 38°C, and the vacuum degree was 0.1Mpa. The residue was subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether:ethyl acetate=9:1, and the ta...

Embodiment 3

[0046]

[0047] Into a 20mL test tube, add 4-bromophenylthiophene sulfoxide (30mg, 0.1mmol) and 1.2-cyclohexanedione (17.1mg, 0.15mmol) successively at room temperature, and add 0.8ml of dichloroethane at the same time, put In a -10°C low-temperature reactor, wait for the reaction system to mix evenly and the reaction body will be -10°C, add trifluoroacetic anhydride (21mg, 0.15mmol), react at a low temperature of -10°C for 4h, and then raise the temperature of the reaction mixture to room temperature (typically 25°C) and stirred at this temperature for 1 min. After completion, the reaction system in the test tube was transferred to a 10ml eggplant-shaped bottle without any post-processing operation. Using a Heidolph rotary evaporator, the rotation speed was 80-100rpm, the temperature was 38°C, and the vacuum degree was 0.1Mpa. The residue was then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethy...

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Abstract

The invention discloses a preparation method for synthesizing polysubstituted cyclic 1,2-diketone by sulfoxide participating in arylation, and the method comprises the following steps: adding a sulfoxide compound, a 1,2-diketone compound and a solvent into a test tube, placing the test tube into a low-temperature reactor at-10 DEG C, adding trifluoroacetic anhydride when the reaction system is uniformly mixed and reduced to-10 DEG C, reacting at-10 DEG C for 4-4.5 hours, then moving to room temperature, and performing rotary evaporation concentration and silica gel column chromatography separation to obtain a product. According to the method, the sulfoxide compound and the cyclic 1,2-diketone compound generate C-C bonds, the whole reaction does not need metal catalysis, and in an organic solvent system, the method is particularly suitable for the synthesis of some drugs, fundamentally eliminates the problems of metal residue and the like, has higher economic applicability, simple operation, high yield and purity of more than 98%. The conditions are mild and the substrate range is wide.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a preparation method for synthesizing multi-substituted ring 1,2-diketones through arylation of sulfoxide. Background technique [0002] For the method of synthesizing multi-substituted ring 1,2-diketones, at present, the main synthesis methods are: due to the inertness of ring 1,2-diketone α-C-H bonds and the competition of O-arylation / alkylation, There are still problems with direct functionalization. To obtain α-substituted cyclic 1,2-diketones, an indirect method was developed. Conversion of cyclic 1,2-diketones to enol ethers or enamines is required to enhance sp under such conditions 2 α-C-H functionalization. Although effective, these stepwise approaches generally require the use of expensive transition metals and high reaction temperatures. [0003] Therefore, it is highly desirable to achieve direct regioselective C–H functionalization of easily...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/34C07C319/14C07C323/22
CPCC07C319/14C07D333/34C07C2601/10C07C323/22
Inventor 孟祥太朱圣臻陈登峰刘辰婧黄申林
Owner NANJING FORESTRY UNIV
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