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

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Problems solved by technology

[0006] Aiming at the shortcomings of the existing synthetic routes, the present invention provides a method for synthe

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

Example Embodiment

[0026] Example 1:

[0027]

[0028] Add 2-phenylbenzoic acid (0.5mmol) and lithium perchlorate (1.0mmol) to a 25mL reaction tube equipped with a magnetic stirrer, and then add 10.0mL acetonitrile; fix the reaction tube on the magnetic stirrer and add Electrodes (platinum cathode, graphite anode) are electrolyzed with a 6mA constant current while stirring the reaction solution uniformly; the mixture is reacted at room temperature (25°C) for 5 hours, the reaction is over; the solvent is removed with a rotary evaporator, and the crude product is 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, 1.5 Hz, 1H), 7.33 (ddd, J = 11.3, 6.5, 2.3 Hz, 2H). 13 C NMR(101MHz, CDCl 3 )δ161.16,...

Example Embodiment

[0029] Example 2:

[0030]

[0031] Use 4'-methyl-[1,1'-biphenyl]-2-carboxylic acid (1b) instead of 2-phenylbenzoic acid (1a), and the others are the same as in Example 1. Column chromatography (petroleum ether: ethyl acetate=20:1, v / v) gave the target product (2b) with 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.

Example Embodiment

[0032] Example 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) with 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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