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Synthetic method of dicyano compound

A synthesis method and compound technology, applied in the field of synthesis of dicyano compounds, can solve the problems of insufficient reaction yield, harsh reaction conditions, lengthy steps, etc., and achieve high-yield reaction effects, mild reaction conditions, and conversion promotion effects.

Inactive Publication Date: 2016-02-17
付思涵
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these existing methods often have lengthy steps, some reaction yields are not high enough, and some reaction conditions are relatively harsh, etc. These problems seriously restrict the application in industrial production.

Method used

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  • Synthetic method of dicyano compound
  • Synthetic method of dicyano compound
  • Synthetic method of dicyano compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of DMF (N,N-dimethylformamide) and polyethylene glycol 200 (PEG-200) at a volume ratio of 1:2) Compound, 300mmol formula (II) compound, 13mmol catalyst aminoferrocene, 150mmol oxidant PhI (TFA) 2 , 6mmol activator Ru 3 (CO) 12 And 15mmol reaction auxiliary agent (being the mixture of 6mmol pinacol borane and 9mmol triethanolamine borate), then be warming up to 60 ℃, and react with stirring at this temperature for 5 hours;

[0037] After the reaction, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, then filtered, and saturated brine was added to the filtrate to fully wash, and then extracted with ethyl acetate shaking for 2-3 times, the organic phases were combined, and anhydrous Dried over magnesium sulfate, concentrated in vacuo, and the residue was separated by 300-400 mesh silica gel...

Embodiment 2

[0040]

[0041] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of DMF (N,N-dimethylformamide) and polyethylene glycol 200 (PEG-200) at a volume ratio of 1:2) Compound, 300mmol formula (II) compound, 13mmol catalyst aminoferrocene, 150mmol oxidant PhI (TFA) 2 , 8mmol activator Ru 3 (CO) 12 And 15mmol reaction auxiliary agent (being the mixture of 6mmol pinacol borane and 9mmol triethanolamine borate), then be warming up to 60 ℃, and react with stirring at this temperature for 5 hours;

[0042]After the reaction, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, then filtered, and saturated brine was added to the filtrate to wash fully, and then extracted with ethyl acetate shaking for 2-3 times, the organic phases were combined, and anhydrous Dried over magnesium sulfate, concentrated in vacuo, and separated the residue by 300-400 mesh silica gel colu...

Embodiment 3

[0045] Reaction formula is with embodiment 1, and concrete reaction process is as follows:

[0046] At room temperature, add 100 mmol of the above formula (I) to an appropriate amount of organic solvent (a mixture of DMF (N,N-dimethylformamide) and polyethylene glycol 200 (PEG-200) at a volume ratio of 1:2) Compound, 350mmol formula (II) compound, 10mmol catalyst aminoferrocene, 200mmol oxidant PhI (TFA) 2 , 6mmol activator Ru 3 (CO) 12 And 12mmol reaction auxiliary agent (being the mixture of 6mmol pinacol borane and 6mmol triethanolamine borate), then be warming up to 50 ℃, and stir reaction at this temperature for 7 hours;

[0047] After the reaction, the reaction system was naturally cooled to room temperature, and the pH value was adjusted to be neutral, then filtered, and saturated brine was added to the filtrate to wash fully, and then extracted with ethyl acetate shaking for 2-3 times, the organic phases were combined, and anhydrous Dried over magnesium sulfate, con...

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Abstract

The invention relates to a synthetic method of a dicyano compound shown in the following formula (III). The method comprises the steps that a compound shown in the following formula (I) and a compound shown in the following formula (II) react in an organic solvent under the effects of a catalyst, an oxidizing agent, a reaction promoter and an activator; after the reaction is over, aftertreatment is conducted, and then the compound shown in the following formula (III) is obtained, wherein R1 refers to C1-C6 alkyl, and R2 refers to phenyl or benzyl. According to the technical scheme, a proper substrate and cyaniding agent as well as the catalyst, the oxidizing agent, the reaction promoter and the activator are adopted, and the organic solvent is selected properly, so that conversion of materials is promoted efficiently, and a high-yield reaction effect is achieved; moreover, reaction conditions are mild, and the method has a broad prospect and scientific research value in industrial application.

Description

technical field [0001] The invention relates to a synthesis method of a dicyano compound, which belongs to the field of organic chemical synthesis. Background technique [0002] In organic chemistry, cyano compounds can be widely used in the construction of biologically active molecules, and they are also important synthetic intermediates in organic synthesis. [0003] Among the cyano compounds, dicyano compounds have attracted the attention of many researchers, because their structure contains two cyano groups, which facilitates subsequent functionalization, such as further reaction to form propanedithioamide, or Cyclization, α-carbon alkylation, or light-induced rearrangement, etc. occur. [0004] So far, there are many reports on the synthetic methods of relevant dicyano compounds in the prior art, for example: [0005] ("ReactionsofS-AIkyl-NN-disstitutedThioamideSalts.Part3.ThiocarbamoylCyanideDerivatives", J.Chem.Soc., PerkinTrans.1, 1979, 2708-2710) reported a prepar...

Claims

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Application Information

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IPC IPC(8): C07C253/16C07C255/24
CPCC07C253/16
Inventor 付思涵
Owner 付思涵
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