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Method for preparing 6-(sulfonylmethyl)phenanthridine compound through electrocatalysis

A technology of sulfonylmethyl compounds, which is applied in the field of electrocatalytic preparation of 6-phenanthridine compounds, can solve the problems of reducing the use of organic solvents, easy pollution of the environment, and the expensive price of terpyridine ruthenium chloride hexahydrate photosensitizers. , to achieve the effect of simple operation steps, mild conditions and cost saving

Active Publication Date: 2020-01-21
CHANGZHOU INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The above technologies require expensive metal ruthenium, which is easy to have metal residues in the product and the cost is high. The photosensitizer of terpyridine ruthenium chloride hexahydrate is relatively expensive, and the market price is 204,000 yuan / Kg, and a specific light source is required. , it is difficult to scale up the preparation of
The reaction system completely uses organic solvents, which is easy to cause pollution to the environment
[0009] However, the electrochemical method is used to make the sulfonyl radicals attack the alkene azide, and make it cyclized to prepare 6-(sulfonylmethyl)phenanthridine compounds, which does not require light, and water and acetonitrile are used as mixed solvents to reduce the impact on organic solvents. The use of similar reaction methods has not yet been reported

Method used

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  • Method for preparing 6-(sulfonylmethyl)phenanthridine compound through electrocatalysis
  • Method for preparing 6-(sulfonylmethyl)phenanthridine compound through electrocatalysis
  • Method for preparing 6-(sulfonylmethyl)phenanthridine compound through electrocatalysis

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Experimental program
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Effect test

Embodiment 1

[0037] The preparation of embodiment 1 6-(tosylmethyl)phenanthridine:

[0038] Under nitrogen, add tetrabutylammonium tetrafluoroborate (26.3 mg, 0.08 mmol), anhydrous potassium carbonate (41.4 mg, 0.3 mmol), 4-methylbenzenesulfonyl hydrazide (55.9 mg , 0.3mmol), distyryl azide (44.2mg, 0.2mmol), with 4mL of acetonitrile and water mixed solvent (acetonitrile and water volume ratio is 18:1) to dissolve the above substances, use carbon electrode as working electrode, platinum sheet The electrode was a counter electrode, and the reaction mixture was reacted for 3 hours under the condition of a constant current of 12 mA. After the reaction was completed, the aqueous phase was extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate, and the reaction solution after separation, extraction, and drying by column chromatography obtained 59.68 mg of a white solid, namely 6-(tosylmethyl) Phenanthridine 59.68 mg, the calculated yield was 86%. The product...

Embodiment 2

[0046] Embodiment 2: the influence of different acetonitrile and water volume ratio on the preparation of 6-(tosylmethyl)phenanthridine

[0047] On the basis of Example 1, further explore the impact of different acetonitrile and water volume ratios on the preparation of 6-(tosylmethyl)phenanthridine, acetonitrile and water according to the volume ratio of 1:1, 10:1, 15:1 , 18:1, and 20:1 were mixed, and other reaction conditions were the same as in Example 1 to prepare 6-(tosylmethyl)phenanthridine respectively, and the results are shown in Table 1. As can be seen from Table 1, when the volume ratio of acetonitrile and water was 1:1, the product quality was only 13.88mg, and the yield was only 20%. When gradually increasing the volume ratio of acetonitrile and water, the quality and yield of the product also increased. Gradually increased, when the volume ratio of acetonitrile and water was 18:1, the product quality reached 59.68 mg, and the yield reached 86%. Continuing to i...

Embodiment 3

[0050] Embodiment 3: the impact of different electrocatalytic currents on the preparation of 6-(tosylmethyl)phenanthridine

[0051] On the basis of Example 1, the influence of different electrocatalytic currents on the preparation of 6-azidomethylphenanthridine was further explored. The energizing current was set to 6mA, 8mA, 10mA, 12mA, 16mA, 20mA, and other reaction conditions were the same as in Example 1 to prepare 6-azidomethylphenanthridine respectively. The results are shown in Table 2. As can be seen from Table 2, when the electrocatalytic current is 6mA, the product quality is 5.55mg, and the yield is only 8%. When the electrocatalytic current is gradually increased, the quality and yield of the product are also gradually improved. When the electrocatalytic current increases to At 12mA, the product quality reached 59.68mg, and the yield reached 86%. When the electrocatalytic current was further increased, the quality and yield of the product began to decrease again. ...

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Abstract

The invention discloses a method for preparing a 6-(sulfonylmethyl)phenanthridine compound through electrocatalysis, and belongs to the technical field of chemical synthesis. The 6-(sulfonylmethyl)phenanthridine derivative is prepared by utilizing electrocatalysis, so that the defects that in the prior art, a sulfonyl substituted phenanthridine compound reaction route requires an oxidizing agent and a metal catalyst, and has high requirements on equipment, a relatively high cost, and the like are overcome. Organic electrochemical catalysis directly or indirectly realizes an oxidation-reductionreaction by virtue of electron gain and loss on the surface of an electrode, so that the use of toxic and harmful oxidation-reduction reagents can be avoided.

Description

technical field [0001] The invention relates to a method for electrocatalytically preparing 6-(sulfonylmethyl)phenanthridine compounds, which belongs to the technical field of chemical synthesis. Background technique [0002] Phenanthridine derivatives are a relatively important class of organic compounds. From natural biologically active products to artificially synthesized pharmaceutical preparations and functional materials, phenanthridine derivatives have great practical significance. In addition, the sulfonyl group is a very important and common functional group in the field of organic synthesis. The sulfonyl group exists in many biologically active natural products and drug molecules. Moreover, the sulfonyl group can be converted into a sulfur group through chemical reactions. , sulfoxide and other functional groups, how to efficiently introduce sulfonyl groups into organic molecules, especially organic molecules with biological activity, has been a subject of great co...

Claims

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Application Information

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IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 孔宪强林隆胥波
Owner CHANGZHOU INST OF TECH
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