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Preparation method of naphthalenone compound

The technology of a compound and a synthetic method is applied in the field of preparation of naphthone compounds, and can solve the problems of environmental pollution, narrow substrate adaptation range, etc.

Active Publication Date: 2018-11-23
NANCHANG HANGKONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, these traditional methods still have shortcomings such as narrow substrate adaptability and environmental pollution.

Method used

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  • Preparation method of naphthalenone compound
  • Preparation method of naphthalenone compound
  • Preparation method of naphthalenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 20

[0046]

[0047] Add 2-bromopropiophenone (0.2mmol) shown in the formula I-1 to the Schlenk lock reactor, p-methylphenylacetylene (0.1mmol) shown in the formula II-2, Cu(MeCN) 4 PF 6 (10mol%), 1,10-phen (20mol%), K 2 CO 3 (2equiv) and toluene (2mL), under argon atmosphere, the reaction was stirred at 120°C, and the reaction was detected by TLC (about 16 hours), and then the reaction solution was filtered through a short silica gel column, and ethyl acetate washed the filter cake, and the Concentrate under reduced pressure to obtain a residue, which is separated by silica gel column chromatography to obtain the target product of formula III-2. Yield 78%; d.r.=1:1; colorless oily liquid; 1 H NMR (400MHz, CDCl 3)δ:8.17(d,J=7.6Hz,0.5H),8.03(d,J=8.0Hz,1H),7.97(d,J=7.6Hz,0.5H),7.84(d,J=7.6Hz, 1H),7.59-7.36(m,5H),7.30-7.20(m,5H),6.51(s,0.5H),6.19(s,0.5H),4.41-4.29(m,1H),2.41(s, 3H), 1.39(s, 1.50H), 1.36(d, J=7.2Hz, 1.50H), 1.29(s, 1.50H), 1.14(d, J=6.8Hz, 1.50H).; 13 C NMR (...

Embodiment 21

[0049]

[0050] Add 2-bromopropiophenone (0.2mmol) shown in the formula I-1 to the Schlenk lock reactor, p-chlorophenylacetylene (0.1mmol) shown in the formula II-3, Cu(MeCN) 4 PF 6 (10mol%), 1,10-phen (20mol%), K 2 CO 3 (2equiv) and toluene (2mL), under argon atmosphere, the reaction was stirred at 120°C, and the reaction was detected by TLC (about 16 hours), and then the reaction solution was filtered through a short silica gel column, and ethyl acetate washed the filter cake, and the Concentrate under reduced pressure to obtain a residue, which is separated by silica gel column chromatography to obtain the target product of formula III-3. Yield 75%; d.r.=1.5:1; white solid; 1 H NMR (400MHz, CDCl 3 )δ: 8.19(d, J=7.6Hz, 0.41H), 8.04(d, J=7.6Hz, 0.82H), 7.98(d, J=7.6Hz, 0.66H), 7.85(d, J=7.6Hz ,1.28H),7.52-7.32(m,9H),7.14(t,J=7.6Hz,1H),6.54(s,0.41H),6.22(s,0.62H),4.41-4.33(m,1H) ,1.39(s,1.82H),1.37(d,J=6.8Hz,1.87H),1.30(s,1.21H),1.13(d,J=6.8Hz,1.23H); 13 C NMR (100MH...

Embodiment 22

[0052]

[0053] Add 2-bromopropiophenone (0.2mmol) shown in the formula I-1 to the Schlenk lock reactor, p-acetylphenylacetylene (0.1mmol) shown in the formula II-4, Cu(MeCN) 4 PF 6 (10mol%), 1,10-phen (20mol%), K 2 CO 3 (2equiv) and toluene (2mL), under argon atmosphere, the reaction was stirred at 120°C, and the reaction was detected by TLC (about 16 hours), and then the reaction solution was filtered through a short silica gel column, and ethyl acetate washed the filter cake, and the Concentrate under reduced pressure to obtain a residue, which is separated by silica gel column chromatography to obtain the target product of formula III-4. Yield 54%; d.r.>20:1; colorless oily liquid; 1 H NMR (400MHz, CDCl 3 )δ: 8.02(t, J=8.4Hz, 3H), 7.86(d, J=7.6Hz, 2H), 7.54-7.45(m, 4H), 7.41(t, J=7.6Hz, 2H), 7.34( t,J=7.6Hz,1H),7.13(d,J=8.0Hz,1H),6.27(s,1H),4.45-4.32(m,1H),2.66(s,3H),1.41(s,3H ), 1.38(d, J=6.8Hz, 3H); 13 C NMR (100MHz, CDCl 3 )δ: 202.8, 202.8, 197.7, 144.8, 137....

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Abstract

The invention provides a synthesis method for preparing a naphthalenone compound with the advantages of simple process, low cost and wide reaction substrate reaction range. According to the method, 2-brom-acetophenone compounds are used as raw materials; heating reaction is performed under the conditions of copper catalysts, ligand, alkali, organic solvents and inert atmosphere; the naphthalenonecompound can be conveniently prepared at excellent yield.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a preparation method of naphthalenone compounds. Background technique [0002] As important chemical products and intermediates, naphthalenones are widely used in medicine, pesticides, dyes and other fields. In the pesticide industry, it is used to produce insecticides, herbicides, etc.; in the dye industry, it is used to produce anthraquinone dyes; in the pharmaceutical industry, it is mainly used to produce drug intermediates such as sertraline. At present, the methods for synthesizing naphthalene compounds are mainly through the oxidation of tetralin derivatives, the condensation of aromatic ring compounds and γ-butyrolactone, and the cyclization of γ-phenylbutyryl chloride. However, these traditional methods still have shortcomings such as narrow substrate adaptability and environmental pollution. [0003] Yu Shouyun et al. reported a method for preparing poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/72C07D333/22C07C49/792C07C49/813C07C49/84C07B37/10
CPCC07B37/10C07C45/72C07D333/22C07C2601/02C07C2601/16C07C2602/10C07C49/792C07C49/813C07C49/84
Inventor 李金恒宋仁杰胡超
Owner NANCHANG HANGKONG UNIVERSITY
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