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A new method based on nitration/cyclization of 1,6-enynes

A cyclization reaction and compound technology, applied in chemical instruments and methods, organic radical generation, organic chemistry, etc., can solve the problems of low reaction atom economy, uncontrollable reaction system, low regioselectivity, etc., and achieve good Application prospect, low cost, and the effect of improving reaction efficiency

Active Publication Date: 2021-05-04
YANGTZE NORMAL UNIVERSITY
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  • Claims
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AI Technical Summary

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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  • A new method based on nitration/cyclization of 1,6-enynes
  • A new method based on nitration/cyclization of 1,6-enynes
  • A new method based on nitration/cyclization of 1,6-enynes

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Experimental program
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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 new method based on the nitration / cyclization reaction of 1,6-enynes. 1,6-enyne compound and copper nitrate are used as raw materials in a solvent, and then a nitration / cyclization reaction is carried out under the action of an oxidizing agent until the raw materials are completely reacted, and then a nitro-substituted 2-pyrrolidone compound is obtained through post-treatment. The nitration reaction process does not require the participation of water in the solvent and does not need to experience nitrous acid, a highly acidic intermediate, which greatly simplifies the reaction process and is carried out under neutral conditions, and has a wide range of hydrogen sources. The nitro-substituted product was prepared with high regioselectivity and high yield under the oxidation system. The method has the advantages of simple operation, cheap and easy-to-obtain raw materials, low cost, wide range of reaction substrates, mild reaction conditions, high efficiency and stability, and is especially suitable for industrial production with good application prospects. a new way of thinking.

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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Patent Type & Authority Patents(China)
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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