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Method for modifying diaryl dihydrophenazine through light adjustment.

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

Active Publication Date: 2021-07-30
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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  • Method for modifying diaryl dihydrophenazine through light adjustment.
  • Method for modifying diaryl dihydrophenazine through light adjustment.
  • Method for modifying diaryl dihydrophenazine through light adjustment.

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: At room temperature, add polytetrafluoroethylene magnetic stirrer, 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 bottle was placed under the condition of light (420-430nm) and reacted for 24 hours. Separation was carried out by column chromatography to obtain the product Product-1 (pale yellow solid, 79 mg, conversion rate 89%).

Embodiment 2

[0029] Example 2: At room temperature, add polytetrafluoroethylene magnetic stirrer, 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 the rubber stopper and seal it, replace The air in the bottle was vented and flushed with nitrogen. Then the reaction bottle was placed under the condition of light (420-430 nm) and reacted for 24 hours. Separation was carried out by column chromatography to obtain the product Product-2 (pale yellow solid, 75 mg, conversion rate 86%).

Embodiment 3

[0030] Example 3: At room temperature, add polytetrafluoroethylene magnetic stirrer, 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 the rubber stopper and seal it, replace The air in the bottle was vented and flushed with nitrogen. Then the reaction bottle was placed under the condition of light (420-430 nm) and reacted for 24 hours. Separation was carried out by column chromatography to obtain the product Product-3 (pale yellow solid, 82 mg, conversion rate 94%).

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Abstract

The invention discloses a novel method for modifying diaryl dihydrophenazine through light adjustment. The core modification of the diaryl dihydrophenazine is carried out by a three-component olefin alkylarylation. The preparation method comprises the following steps: dissolving a styrene compound, halogenated alkyl acid ester and diaryl dihydrophenazine in a solvent, reacting under illumination, and separating after the reaction to obtain the modified diaryl dihydrophenazine. No metal catalyst is used in the modification process, and the reaction is green and environment-friendly. The synthesis method of the diaryl dihydrophenazine is widened, the structure of the compound is enriched, and the diaryl dihydrophenazine compound has potential application prospects in the fields of materials and organic catalysis.

Description

technical field [0001] The invention belongs to the field of organic synthesis and photochemistry, and specifically relates to a new method for photoregulating the modification of diaryldihydrophenazine. Background technique [0002] 5,10-diaryl-5,10-dihydrophenazines (DADHPs) have received extensive attention due to their good magnetic properties. In addition, 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) The C–N coupling of aryl halides and dihydrophenazines catalyzed by copper or palladium catalysts is a common method for the synthesis of DADHPs. 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 ...

Claims

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Application Information

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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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