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Synthesis method of polyaryls six-membered ring lactone compound

A technology of ester compounds and aryl six-membered rings, which is applied in the field of organic compound synthesis to achieve the effects of mild conditions, wide substrate applicability, simple and safe operation

Active Publication Date: 2018-03-16
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the shortcomings of the existing synthetic routes, the present invention provides a method for synthesizing biaryl six-membered ring lactone compounds, which has the advantages of simple process and convenient operation.

Method used

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  • Synthesis method of polyaryls six-membered ring lactone compound
  • Synthesis method of polyaryls six-membered ring lactone compound
  • Synthesis method of polyaryls six-membered ring lactone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Add 2-phenylbenzoic acid (0.5mmol) and lithium perchlorate (1.0mmol) to a 25mL reaction tube equipped with a magnetic stirrer, then add 10.0mL acetonitrile; fix the reaction tube on a magnetic stirrer, add The electrodes (platinum sheet cathode, graphite anode) were electrolyzed with a 6mA constant current, and the reaction solution was uniformly stirred at the same time; after the mixture was reacted at room temperature (25°C) for 5h, the reaction was completed; the solvent was removed with a rotary evaporator, and the crude product was subjected to column chromatography ( Petroleum ether:ethyl acetate=20:1, v / v) The target product (2a) was obtained by separation and purification with a yield of 85%. The NMR data of this compound are: 1 H NMR (400MHz, CDCl 3 )δ8.38(dd, J=7.9,0.9Hz,1H),8.09(d,J=8.1Hz,1H),8.03(dd,J=7.9,1.3Hz,1H),7.89–7.73(m,1H ),7.67–7.53(m,1H),7.47(ddd,J=8.4,7.3,1.5Hz,1H),7.33(ddd,J=11.3,6.5,2.3Hz,2H). 13 C NMR (101MHz, CDCl 3 )δ161.16, ...

Embodiment 2

[0030]

[0031] 4'-methyl-[1,1'-biphenyl]-2-carboxylic acid (1b) was used instead of 2-phenylbenzoic acid (1a), and the others were the same as in Example 1. Column chromatography (petroleum ether: ethyl acetate = 20:1, v / v) gave the target product (2b) in a yield of 88%. The NMR data of this compound are: 1 H NMR (400MHz, CDCl 3 )δ8.37(dd, J=8.0,1.0Hz,1H),8.07(d,J=8.1Hz,1H),7.92(d,J=7.9Hz,1H),7.86–7.73(m,1H), 7.64–7.43(m,1H),7.14(d,J=8.7Hz,2H). 13 C NMR (101MHz, CDCl 3 )δ161.44, 151.24, 141.28, 134.97, 134.77, 130.51, 128.35, 125.66, 122.49, 121.42, 120.84, 117.86, 115.40, 21.44.

Embodiment 3

[0033]

[0034] 4'-fluoro-[1,1'-biphenyl]-2-carboxylic acid (1c) was used instead of 2-phenylbenzoic acid (1a), and the others were the same as in Example 1. Column chromatography (petroleum ether:ethyl acetate=20:1, v / v) gave the target product (2c) in a yield of 93%. The NMR data of this compound are: 1 H NMR (400MHz, CDCl 3 )δ8.34(dd, J=8.0,1.0Hz,1H),8.00(dd,J=8.3,5.6Hz,2H),7.86–7.74(m,1H),7.61–7.48(m,1H),7.12 –6.97(m,2H). 13 C NMR (101MHz, CDCl 3 )δ163.41(d, J=251.3Hz), 160.75, 152.08(d, J=12.3Hz), 135.07, 134.16, 130.61, 128.74, 124.34(d, J=9.9Hz), 121.48, 120.35, 114.56(d , J=3.2Hz), 112.42(d, J=22.4Hz), 105.03(d, J=25.3Hz). 19 F NMR (376MHz, CDCl 3 )δ-108.36(s).

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Abstract

The invention discloses a synthesis method of a polyaryls six-membered ring lactone compound. 2-aryl benzoic acid is used as a raw material, C-O cyclizing is achieved through constant current electrolysis under existence of a supporting electrolyte, and the polyaryls six-membered ring lactone compound is obtained after separating and purifying. According to the synthesis method of the polyaryls six-membered ring lactone compound, the polyaryls six-membered ring lactone compound is synthetized by using an electrochemistry method, has the characteristics that the polyaryls six-membered ring lactone compound is high in atom economy, green and efficient, using of a metal catalyst and an oxidant is avoided, and the technology is simple, and the synthesis method of the polyaryls six-membered ring lactone compound is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of a biaryl six-membered ring lactone compound, belonging to the field of organic compound synthesis. Background technique [0002] Biaryl six-membered ring lactones widely exist in important natural products and drug molecules [1] . In recent years, the preparation of biaryl six-membered ring lactones by activating C-O ring closure through aromatic C-H bonds has been intensively studied and made important progress [2] . However, the existing technical routes require the use of expensive transition metal catalysts, excessive oxidants, and harsh reaction conditions, which limit the practicability of these synthetic methods. [0003] 【references】 [0004] [1] (a) B.I.Alo, A.Kandil, P.A.Patil, M.J.Sharp, M.A.Siddiqui and V.Snieckus, J.Org.Chem., 1991, 56, 3763; (b) H.Abe, K.Nishioka, S .Takeda, M.Arai, Y.Takeuchi and T.Harayama, Tetrahedron Lett., 2005, 46, 3197; (c) K.Koch, J.Podlech, E.Pfeiffer and M.Metz...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 戴建军周洁陶香长许华建
Owner HEFEI UNIV OF TECH
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