Synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative

A technology of benzofuran and nitrofurane, which is applied in directions such as organic chemistry, can solve the problems of few reaction substrates, high product price, inconsistency, etc., and achieves simplified reaction operation and post-processing process, easy availability of raw materials, The effect of reducing pollution

Inactive Publication Date: 2010-01-20
SUZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the above-mentioned prior art: reactant 2-chloro-2-nitrostyrene, 2-bromo-2-nitrostyrene and their analogs are difficult to prepare (many steps), which results in few reaction substrates , the cost is high, and the pollution caused thereby is many (halogen must first enter the raw material, and finally it will be eliminated from the product, which not only causes a lot of pollution, but also causes a great waste (does not meet the green chemical requirements of atom economy) ), leading to expensive products

Method used

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  • Synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative
  • Synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative
  • Synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Dissolve 1 mmol of β-nitrostyrene, 2 mmol of manganese acetate, and 1 mmol of 1,3-cyclic diketone in 10 ml of water, 95% ethanol, 80% ethanol, 50% ethanol, absolute ethanol, and acetic acid , acetonitrile, and the reaction solution is placed in a water bath and heated to 60 ° C, TLC tracking reaction shows that the best reaction effect (86% yield) in 95% ethanol, the results are as follows:

[0049] solvent

Embodiment 2

[0050] Example 2: Dissolve 1 mmol of β-nitrostyrene, 2 mmol of manganese acetate, and 1 mmol of 1,3-cyclic diketone in 10 ml of 95% ethanol at 20°C, 30°C, 40°C, 50°C, and 60°C, respectively. Reaction, TLC follow-up reaction shows that reaction effect is the best (productive rate 86%) at 50 ℃, the result is as follows:

[0051] temperature(℃)

Embodiment 3

[0052] Example 3: 1 mmol of β-nitrostyrene, 2 mmol of manganese acetate, and 1 mmol, 2 mmol, and 3 mmol of 1,3-cyclic diketone were respectively dissolved in 95% ethanol and reacted at 50° C. TLC tracking reaction showed 1, When the amount of 3-cyclic diketone is 2mmol, the reaction yield is the highest (productive rate 86%), and the results are as follows:

[0053] Manganese acetate (mmol)

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Abstract

The invention discloses a synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivatives, comprising the following steps: adopting one of beta-nitrostyrolene, beta-nitrofurylethylene, beta-nitrothienylethylene, beta-nitropyrrylethylene or beta-nitropyridylethylene or one of derivative thereof and 1,3-macrocyclicdiketone as reactants to react at 30-70 DEG C and preparing the 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative. In the method of the invention, the raw materials are cheap, accessible and various, the synthesized products have various types and the products can be used as potential molecules with biological activity and important key intermediates; the invention adopts ethanol as reaction medium so as to reduce the pollution, shorten the reaction time, simplify the reaction process and the post-treatment process and reduce the production cost. The method of the invention has the advantages that the regioselectivity and the stereoselectivity are good, the yield is high, the addition reaction and the cyclization reaction can be realized by one-pot method and the process is simple.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivatives. Background technique [0002] Dihydrofuran derivatives are a class of physiologically active substances and are also very important synthetic intermediates. They can be oxidized to synthesize furan derivatives, and can also be reduced to obtain tetrahydrofuran derivatives, which are further used in the synthesis of drugs and important natural products. Synthesizing. [0003] In the prior art, there are only two reports on the preparation of 6,6-dimethyl-2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one: [0004] (1) Daniel Dauzonne reported the generation of dihydrofuran derivatives by reacting 5,5-dimethyl-1,3-cyclohexanedione with 2-chloro-2-nitrostyrene in the presence of potassium fluoride, the reaction Heating to reflux in anhydrous ethylene glycol dimethyl ether solvent for 24 hours g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/82C07D409/04C07D405/04
Inventor 邹建平王磊潘向强
Owner SUZHOU UNIV
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