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A kind of synthetic method of biaryl 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, simple and safe operation, and wide applicability of substrates

Active Publication Date: 2019-05-28
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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  • A kind of synthetic method of biaryl six-membered ring lactone compound
  • A kind of synthetic method of biaryl six-membered ring lactone compound
  • A kind of synthetic method of biaryl 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 biaryl six-membered ring lactone compound, which uses 2-arylbenzoic acid as a raw material, realizes C-O cyclization by constant current electrolysis in the presence of a supporting electrolyte, and separates and purifies the compound. After that, the biaryl six-membered ring lactone compound is obtained. The synthesis by the electrochemical method of the present invention has the characteristics of high atom economy, green and high efficiency, avoiding the use of metal catalysts and oxidants, simple process and the like, and 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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Patent Type & Authority Patents(China)
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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