A kind of method of light-adjusting diaryldihydrophenazine modification

A technology of diaryldihydrophenazine and light regulation, applied in the direction of organic chemistry and the like, can solve the problems of many reaction steps, low yield, low final product yield, etc., and achieve the effect of high reaction yield

Active Publication Date: 2022-08-09
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in order to synthesize DADHPs with complex structures, it is often necessary to pre-functionalize the precursors, which not only requires many reaction steps and the yield of the final product is low; (2) DADHPs can be prepared by thermal rearrangement of tetraaryl hydrazides, but this method produces (3) Iron-catalyzed diarylamine C-F amination is a relatively simple method for the synthesis of DADHPs, but this method can only synthesize DADHPs with relatively simple structures

Method used

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  • A kind of method of light-adjusting diaryldihydrophenazine modification
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  • A kind of method of light-adjusting diaryldihydrophenazine modification

Examples

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Effect test

Embodiment 1

[0028] Example 1: At room temperature, into a 20mL transparent glass sample bottle were sequentially added polytetrafluoroethylene magnetic stirring bar, DHDAP-1 (50mg, 0.0889mmol, 1eq), styrene (93mg, 0.8892mmol, 10eq), 2-bromo - Ethyl 2-methylpropionate (347mg, 1.7785mmol, 20eq), sodium carbonate (20mg, 0.1778mmol, 2eq), 1,4-dioxane (5mL), plugged with a rubber stopper and sealed, replaced Air in the bottle and flush with nitrogen. Then, the reaction flask was placed under light (420-430 nm) conditions, and the reaction was performed for 24 h. Separation by column chromatography gave the product Product-1 (pale yellow solid, 79 mg, conversion 89%).

Embodiment 2

[0029] Example 2: At room temperature, into a 20mL transparent glass sample bottle were sequentially added polytetrafluoroethylene magnetic stirring bar, DHDAP-2 (50mg, 0.0847mmol, 1eq), styrene (88mg, 0.847mmol, 10eq), 2-bromo - Ethyl 2-methylpropionate (330mg, 1.694mmol, 20eq), sodium carbonate (18mg, 0.1694mmol, 2eq), 1,4-dioxane (5 mL), plug with rubber stopper and seal, replace Air out of the bottle and flushed with nitrogen. The reaction flask was then placed under light (420-430 nm) conditions for 24 hours of reaction. Separation by column chromatography gave the product Product-2 (pale yellow solid, 75 mg, 86% conversion).

Embodiment 3

[0030] Example 3: At room temperature, into a 20mL transparent glass sample bottle were sequentially added polytetrafluoroethylene magnetic stirring bar, DHDAP-3 (50mg, 0.0847mmol, 1eq), styrene (88mg, 0.847mmol, 10eq), 2-bromo - Ethyl 2-methylpropionate (330mg, 1.694mmol, 20eq), sodium carbonate (18mg, 0.1694mmol, 2eq), 1,4-dioxane (5 mL), plug with rubber stopper and seal, replace Air out of the bottle and flushed with nitrogen. The reaction flask was then placed under light (420-430 nm) conditions for 24 hours of reaction. Separation by column chromatography gave the product Product-3 (pale yellow solid, 82 mg, 94% conversion).

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Abstract

The invention discloses a new method for light-adjusting diaryldihydrophenazine modification. Nucleus modification of diaryldihydrophenazines by three-component alkene alkylarylation. The styrene compound, the halogenated alkyl ester and the diaryldihydrophenazine are dissolved in a solvent and then reacted under light, and the modified diaryldihydrophenazine is obtained by separation after the reaction is completed. No metal catalyst is used in this modification process, and the reaction is green and environmentally friendly. The invention broadens the synthesis method of diaryldihydrophenazine, enriches the structure of such compounds, and has potential application prospects in the field of materials and organic catalysis.

Description

technical field [0001] The invention belongs to the field of organic synthesis and photochemistry, and in particular relates to a new method for adjusting the modification of diaryldihydrophenazine by light. Background technique [0002] 5,10-Diaryl-5,10-dihydrophenazines (DADHPs) have received extensive attention due to their good magnetic properties, and DADHPs are also widely used in organic light-emitting materials and photocatalysis. However, the methods for synthesizing such compounds are limited, and it is difficult to synthesize DADHPs with complex structures using existing synthetic methods. (1) C-N coupling of aryl halides and dihydrophenazine catalyzed by copper or palladium catalysts is a common method for the synthesis of DADHPs. However, in order to synthesize DADHPs with complex structures, pre-functionalization of the precursors is often required, which not only has many reaction steps but also has a low yield of the final product; (2) DADHPs can be prepared...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/46
CPCC07D241/46
Inventor 沈磊李玉光掌亚军杨阳高铭陈茜
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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