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Method for preparing polyaromatic substituted naphthalene derivative by catalyzing cyclization reaction of aromatic ketone and diphenyl acetylene by ruthenium and application

A technology of tolanyl and naphthalene derivatives, which is applied in the field of preparation of polyaromatic substituted naphthalene derivatives, can solve problems such as increasing production costs, and achieve the effect of simple and easy synthesis methods

Active Publication Date: 2018-05-01
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are defects in this method. These reactions require a certain amount of ligand or an equivalent metal salt as an oxidant to complete the catalytic cycle, which not only increases the production cost, but also the metal salts are mostly heavy metal (copper, silver, etc.) salts that pollute the environment.

Method used

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  • Method for preparing polyaromatic substituted naphthalene derivative by catalyzing cyclization reaction of aromatic ketone and diphenyl acetylene by ruthenium and application
  • Method for preparing polyaromatic substituted naphthalene derivative by catalyzing cyclization reaction of aromatic ketone and diphenyl acetylene by ruthenium and application
  • Method for preparing polyaromatic substituted naphthalene derivative by catalyzing cyclization reaction of aromatic ketone and diphenyl acetylene by ruthenium and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] To a 25mL sealed tube with a magnet, add toluene (18mg, 0.1mmol), the corresponding aromatic ketone (0.2mmol), catalyst [RuCl 2 (p-cymene)] 2 (9mg, 15% mol), 0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol) and potassium acetate (19mg, 0.2mmol), replace nitrogen three times, react at 100°C for 24 hours, then pass column chromatography Separation (eluent: petroleum ether) to obtain the target compound. Characterization is as follows.

[0023] 4,5-Diphenyl-6-(thiophene-2-methylene)benzo[b]thiophene: Yield: 40%. 1 H NMR (CDCl 3 ,400MHz)δ7.81(s,1H),7.33(d,J=5.2Hz,1H),7.10-7.18(m,9H),7.00-7.02(m,3H),6.87(dd,J 1 = 3.6Hz; J 2 =5.2Hz,1H),6.59-6.60(m,1H),4.07(s,2H). 13 C NMR (CDCl 3 ,100MHz)δ144.1,139.7,139.4,135.7,130.8,130.4,127.5,126.7,126.5,126.4,125.9,124.2,123.8,122.1,34.5. 25 h 18 S 2 (M + ):382.0850,found:382.0847.

Embodiment 2

[0025]

[0026] To a 25mL sealed tube with a magnet, add toluene (18mg, 0.1mmol), the corresponding aromatic ketone (0.2mmol), catalyst [RuCl 2 (p-cymene)] 2 (9mg, 15% mol), 0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol) and potassium acetate (19mg, 0.2mmol), replace nitrogen three times, react at 100°C for 24 hours, then pass column chromatography Separation (eluent: petroleum ether) to obtain the target compound. Characterization is as follows.

[0027] 3-Methyl-1,2,7-triphenylnaphthalene: Yield: 65%. Melting point: 163-165°C. 1 H NMR (CDCl 3 ,400MHz)δ7.91(d,J=8.4Hz,1H),7.79(s,1H),7.69-7.73(m,2H),7.52(d,J=7.2Hz,2H),7.37(t,J =8.0Hz, 2H), 7.29(d, J=7.2Hz, 1H), 7.10-7.23(m, 8H), 7.02-7.05(m, 2H), 2.26(s, 3H). 13 CNMR (CDCl 3 ,100MHz)δ141.5,140.6,140.4,139.2,139.0,137.9,134.7,132.1,131.5,131.1,130.1,128.8,127.7,127.6,127.5,127.4,127.2,127.1,126.4,120.5HR (EI-TOF) calcd for C 29 h 22 (M + ):370.1722,found:370.1723.

Embodiment 3

[0029]

[0030] To a 25mL sealed tube with a magnet, add toluene (18mg, 0.1mmol), the corresponding aromatic ketone (0.2mmol), catalyst [RuCl 2 (p-cymene)] 2 (9mg, 15% mol), 0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol) and potassium acetate (19mg, 0.2mmol), replace nitrogen three times, react at 100°C for 24 hours, then pass column chromatography Separation (eluent: petroleum ether) to obtain the target compound. Characterization is as follows.

[0031] 3-Ethyl-1,2-diphenylnaphthalene: Yield: 25%. Melting point: 124-125°C. 1 H NMR (CDCl 3,400MHz)δ7.79-7.81(m,1H),7.72(s,1H),7.37-7.40(m,2H),7.22-7.26(m,1H),7.01-7.14(m,8H),6.96- 6.98(m,2H),2.51(dd,J 1 =7.6Hz;J 2 =14.8Hz, 2H), 1.08(t, J=7.6Hz, 3H). 13 C NMR (CDCl 3 ,100MHz)δ140.4,140.3,139.6,139.5,138.8,133.0,131.2,131.0,130.4,127.4,127.4,126.8,126.3,126.1,125.8,125.7,125.3,27.4,15.1. 24 h 20 (M + ):308.1565,found:308.1567.

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Abstract

The invention relates to a method for preparing a polyaromatic substituted naphthalene derivative by catalyzing cyclization reaction of aromatic ketone and diphenyl acetylene by ruthenium and application. The method comprises the following steps of using relatively cheap ruthenium as a catalyst, and activating aromatic ketone beta-H to synthesize a hexatomic ring to generate the polyaromatic substituted naphthalene derivative; in the reaction process, no additive or oxidizing agent needs to be added, only a simple alkali is used, and the reaction process is performed in a mild reaction condition. The synthetic method provided by the invention is simple and easy to perform, scientific, reasonable, green, environmentally friendly, economical, practical and suitable for large-scale production.

Description

technical field [0001] The invention relates to the fields of medical technology and photoelectric materials, and mainly relates to a preparation method and application of polyaromatic substituted naphthalene derivatives. Background technique [0002] Due to their unique electrochemical and photochemical properties and their application in n-conjugated functional materials, polyaromatic substituted naphthalene derivatives are more and more widely used in organic fluorescent materials, semiconductor materials, etc., and polyaromatic substitution Naphthalene derivatives also have important applications in drug synthesis. The preparation method adopted in the prior art has made a great breakthrough compared with the relatively harsh conditions of the previous cyclometallation, aryl halide, aryl acid and the like. At present, under mild conditions, polyaromatic substituted naphthalene derivatives are prepared by the cyclization reaction of the C-H bond (even double C-H bond) of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/54C07C1/207C07C15/24C07C17/263C07C25/22C07C22/08C09K11/06
CPCC07C1/2076C07C2/867C07C15/24C07C17/263C07C17/2637C07C22/08C07C25/22C07C51/00C07C2531/22C07D333/54C09K11/06C09K2211/1007C09K2211/1011C09K2211/1092C07C65/105
Inventor 张殊佳高杰
Owner DALIAN UNIV
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