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Method for preparing isocoumarin compounds with o-halo methyl benzoate and terminal alkyne

A technology of methyl benzoate and terminal alkyne, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions and low product selectivity, and achieve the effects of simple reaction operation, multiple types and high yield

Active Publication Date: 2016-01-06
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, people such as AidhenIS have reported two-step synthesis of 3-aryl-substituted isocoumarin compounds by 2-(bromomethyl)methyl benzoate, but these reactions are mostly multi-step reactions, and the selectivity of the product is low, or the bottom substances need to be pre-functionalized, and the reaction conditions are harsh

Method used

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  • Method for preparing isocoumarin compounds with o-halo methyl benzoate and terminal alkyne
  • Method for preparing isocoumarin compounds with o-halo methyl benzoate and terminal alkyne

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0024] Synthesis of 3-Phenylisocoumarin

[0025] Add 0.22mmol methyl o-bromobenzoate, 0.20mmol phenylacetylene, 0.02mmol cuprous iodide, 0.40mmol sodium hydroxide, and 1.0mL acetonitrile solvent into the reactor. Under nitrogen atmosphere, heat to 100°C, keep stirring for 24h, stop the reaction, cool to room temperature, add saturated ammonium chloride solution for washing, extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography The target product was obtained with a yield of 96%. 1 HNMR (400MHz, CDCl 3 ):δ8.31(d,J=8.1Hz,1H),7.88(d,J=6.7Hz,2H),7.72(t,J=7.6Hz,1H),7.51-7.40(m,5H),6.96 (s,1H).

Synthetic example 2

[0027] Synthesis of 3-(2-methylphenyl)isocoumarin

[0028] Add 0.20mmol methyl o-bromobenzoate, 0.20mmol 2-ethynyltoluene, 0.02mmol cuprous iodide, 0.40mmol sodium hydroxide, and 1.0mL acetonitrile solvent into the reactor. Under nitrogen atmosphere, heat to 100°C, keep stirring for 24h, stop the reaction, cool to room temperature, add saturated ammonium chloride solution for washing, extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography The target product was obtained with a yield of 85%. 1 HNMR (400MHz, CDCl 3 ): δ8.31(d, J=7.9Hz, 1H), 7.72(t, J=7.5Hz, 1H), 7.54-7.44(m, 3H), 7.33(t, J=7.4Hz, 1H), 7.30 -7.20(m,2H),6.60(s,1H),2.50(s,3H).

Synthetic example 3

[0030] Synthesis of 3-(4-tert-butylphenyl)isocoumarin

[0031] Add 0.24mmol methyl o-bromobenzoate, 0.20mmol p-tert-butylphenylacetylene, 0.02mmol cuprous iodide, 0.40mmol sodium hydroxide, and 1.0mL acetonitrile solvent into the reactor. Under nitrogen atmosphere, heat to 100°C, keep stirring for 24h, stop the reaction, cool to room temperature, add saturated ammonium chloride solution for washing, extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography The target product was obtained with a yield of 95%. 1 HNMR (400MHz, CDCl 3 ):δ8.30(d,J=7.9Hz,1H),7.82(d,J=8.4Hz,2H),7.70(m,1H),7.49-7.44(m,3H),6.92(s,1H) ,1.35(s,9H).

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Abstract

The invention provides a method for synthesizing isocoumarin compounds with o-halo methyl benzoate and terminal alkyne. According to the method, the synthesis is carried out in a nitrogen atmosphere. A copper catalyst and alkaline reagent are adopted, and the isocoumarin compounds are synthesized directly with o-halo methyl benzoate and terminal alkyne compounds as raw materials. According to the method, inexpensive and easy-to-obtain raw materials and the copper catalyst are adopted, and special reaction conditions such as ligand, acid, peroxide and microwave radiation are not applied. A substrate does not need pre-functionalization. The reaction conditions are mild, operation is simple, and product selectivity and yield are high. The method has potential application prospect in medicine.

Description

【Technical field】 [0001] The invention relates to the fields of organic synthesis and medicine, in particular to a method for preparing isocoumarin compounds from methyl o-halobenzoate and terminal alkynes. 【Background technique】 [0002] Isocoumarin is a benzo six-membered lactone compound, which is a class of natural lactone compounds that widely exist in nature. The derivatives of this type of compound have various pharmacological activities such as antibacterial, anti-allergic, anti-HIV and anti-tumor . For example, 3-phenylisocoumarin is effective against various fungi such as Cochliobolus miyabeanus, Alternaria maritima, Fusarium splendens and Giberellazeae. Growth and reproduction; 3-(4-hydroxyphenyl) isocoumarin has a strong inhibitory effect on Fusarium splendens; isocoumarin NM-3 can resist human multiple myeloma cells. Isocoumarin compounds not only have excellent biological activity but also have variable chemical structures. They are one of the hotspots in the...

Claims

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Application Information

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IPC IPC(8): C07D311/76
CPCC07D311/76
Inventor 周永波孙梦丽苏乐斌董建玉刘龙尹双凤韩立彪
Owner HUNAN UNIV
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