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A kind of 2-h benzopyran derivative and its synthetic method

A technology of benzopyran derivatives and synthesis methods, applied in directions such as organic chemistry, to achieve the effects of low toxicity of raw materials, good adaptability and easy availability

Active Publication Date: 2018-09-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And utilize alkyne ether and enoic acid ester as raw material, under the effect of very small amount of palladium salt, the method that one-step synthetic benzopyran derivative takes place heck reaction also has not reported

Method used

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  • A kind of 2-h benzopyran derivative and its synthetic method
  • A kind of 2-h benzopyran derivative and its synthetic method
  • A kind of 2-h benzopyran derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 0.25 mmoles of phenyl-p-tolyl propargyl ether to a screw-top test tube (preparation method: add 5 mmoles of phenyl propargyl ether, 5 mmoles of p-methyliodobenzene, 0.25 mmoles of Phenylphosphine palladium, 0.5 millimoles of cuprous iodide, 3 milliliters of triethylamine, stirred and reacted at room temperature for 3 hours, then stopped stirring. The reaction mass was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain the Raw materials, the column chromatography eluent used is petroleum ether) (reference: V.S.Prasada RaoLingam.Tetrahedron Letters, 2008,49(27), 4260), 0.25 mmol ethyl acrylate, 0.025 mmol palladium chloride, 0.25 mmol Mole of silver oxide and 2 ml of acetonitrile were stirred and reacted at 80°C for 5 hours, then heating and stirring were stopped, and cooled to room temperature. The reaction material was decompressed and rotary evaporated to remove the solvent, and then separate...

Embodiment 2

[0042] Add 0.25 mmol phenyl-p-tolyl propargyl ether, 0.40 mmol ethyl acrylate, 0.020 mmol palladium acetate, 0.50 mmol silver acetate, 3 ml toluene to a screw-top test tube, stir and react at 70°C for 6 hours, stop Heat and stir, and cool to room temperature. The reaction material was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain 2-H benzopyran derivatives. The column chromatography eluent used was petroleum ether:ethyl acetate with a volume ratio of 5:1 Mixed solvents, yield 80%.

Embodiment 3

[0044] Add 0.25 mmoles of phenyl-p-tolyl propargyl ether, 0.30 mmoles of ethyl acrylate, 0.025 mmoles of palladium carbon, and 2 ml of acetonitrile into a screw-top test tube, cover with an oxygen bulb, stir and react at 90°C for 30 hours, then stop heating And stir, cool to room temperature. The reaction material was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain 2-H benzopyran derivatives. The column chromatography eluent used was petroleum ether:ethyl acetate with a volume ratio of 1:1 Mixed solvents, yield 81%.

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a 2-H benzopyran derivative and a synthesis method thereof. The 2-H benzopyran derivative has a structural formulashown in formula (1), the preparation method is as follows: in a reactor, adding an alkynyl ether, an olefine acid ester and a solvent, adding a palladium salt catalyst and an oxidant, stirring for reacting for 3 to 48 hours at 20 to 150 DEG C, at the end of the reaction, cooling to room temperature, removing the solvent by vacuum evaporation to obtain a crude product, purifying by column chromatography to obtain the 2-H benzopyran derivative. The synthesis method has the advantages of simple and safe operation, easily available raw materials, cheap price, good functional group adaptability, wide substrate adaptability and environment friendliness, and is conducive to industrial production, can be widely used in synthesis of pesticides, pharmaceuticals and natural products.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a 2-Hbenzopyran derivative and a synthesis method thereof. Background technique [0002] With the continuous development of social economy, global environmental pollution and energy consumption problems are becoming more and more serious. In the research of chemical industry, achieving sustainable development has become an important theme. How to develop environmentally friendly new green synthesis methods to achieve efficient use of resources is one of the main directions of organic chemistry progress. [0003] Benzopyran, also known as chromene, has two isomers, α- and γ-. Compounds containing benzopyran ring structures have various biological and pharmacological activities. Reports show that such substances have antibacterial and antifungal properties. , antioxidant and anti-inflammatory activities, in addition to their use as cognitive enhancers for the ...

Claims

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Application Information

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IPC IPC(8): C07D311/04
CPCC07D311/04
Inventor 江焕峰高颖兰高杨伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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