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Novel method based on nitration/cyclization reaction of 1,6-eneyne compound

A cyclization reaction and compound technology, applied in chemical instruments and methods, generation of organic free radicals, organic chemistry, etc., can solve the problems of low reaction atom economy, low regioselectivity, uncontrollable reaction system, etc. Solve the effects of low reactant atom economy, improved reaction efficiency and low cost

Active Publication Date: 2019-11-19
YANGTZE NORMAL UNIVERSITY
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  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a new method based on the nitration / cyclization reaction of 1,6-enyne compounds, which solves the problem of low reaction atom economy in the existing enyne free radical nitration reaction. , the reaction system is uncontrollable, the regioselectivity of the reaction is not high, the reaction efficiency is low and the reaction time is long.

Method used

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  • Novel method based on nitration/cyclization reaction of 1,6-eneyne compound
  • Novel method based on nitration/cyclization reaction of 1,6-eneyne compound
  • Novel method based on nitration/cyclization reaction of 1,6-eneyne compound

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Effect test

Embodiment 1

[0028]

[0029] Add 1,6-enyne compound (39.8mg, 0.2mmol) shown in formula 1a, copper nitrate (74.8mg, 0.4mmol) shown in formula 2a, potassium persulfate (K 2 S2 o 8 , 64.8mg, 0.24mmol) and N,N-dimethylformamide (2mL), then the reactor was stirred and reacted in an air atmosphere at 80°C, and the reaction progress was monitored by TLC until the raw materials disappeared (the reaction time was 4 hours ), after the reaction was completed, the reaction solution was extracted with ethyl acetate into the organic phase, then the obtained organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, the residue was separated by column chromatography, column chromatography The elution solvent in is: ethyl acetate / n-hexane to obtain the target product I-1 (90% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.68(d, J=8.0Hz, 2H), 7.40(t, J=8.0Hz, 2H), 7.20(t, J=7.5Hz, 1H), 5.30(t, J=2.0Hz, 1H) ,5.20(t,J=3.5Hz,1H),4.97(d,J=14.0Hz,...

Embodiment 2

[0031] No oxidizing agent potassium persulfate was added, other conditions were the same as in Example 1, and the yield of the target product I-1 was 0%.

Embodiment 3

[0033] Iodobenzene acetate (PhI(OAc) 2 , 77.3mg, 0.24mmol) instead of potassium persulfate, all the other conditions were the same as in Example 1, and the yield of the target product I-1 was 21%.

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Abstract

The invention relates to a novel method based on a nitration / cyclization reaction of a 1,6-eneyne compound. According to the method, the 1,6-eneyne compound and copper nitrate are used as raw materials and subjected to the nitration / cyclization reaction in a solvent under the action of an oxidizing agent until the raw materials are completely reacted, and then post-treatment is performed to obtaina nitro-substituted 2-pyrrolidone compound; in the process of the nitration reaction, participation of water in the solvent is not needed, and an intermediate with strong acidity such as nitrous acidis not produced, so reaction process is greatly simplified and is carried out under a neutral condition, the nitration reaction process has wide hydrogen sources, and high-regioselectivity and high-yield preparation of the nitro-substituted product is realized in a mild oxidation system. The method has the advantages of simple and convenient operation, usage of cheap and easily available raw materials, low cost, a wide application range of reaction substrates, mild reaction conditions, high efficiency and stability, is particularly suitable for industrial production, presents good applicationprospects, and provides a new thought for free radical nitration reactions.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a highly regioselective nitration / cyclization reaction method of 1,6-enyne compounds under mild conditions involving copper nitrate. Background technique [0002] The nitration reaction of compounds has a wide range of applications in the fields of medicine, pesticides, dyes, and explosives. The traditional nitration reaction using nitric acid mixed acid as a nitration reagent has been widely developed and applied. This method is mature in technology and low in cost, but has low atom economy, seriously pollutes the environment, and has many by-products. After the 1990s, with the enhancement of people's awareness of environmental protection and sustainable development, the nitrification reaction began to develop from the traditional nitrification method to a clean and green direction. The free radical nitration reaction has attracted wide attention from chemists due...

Claims

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Application Information

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IPC IPC(8): C07D207/38C07D207/48
CPCC07B61/02C07D207/38C07D207/48
Inventor 吴燕陈锦杨吴红谕陈睿
Owner YANGTZE NORMAL UNIVERSITY
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