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Benzofuranone/ naphthofuranone aryl imine compound and synthetic method thereof

A technology of furanone aryl imine and synthesis method, which is applied in the field of benzo/naphthofuranone aryl imine compounds and their synthesis, can solve the problems of harsh reaction conditions and unproposed applicability, and achieve functional group compatibility Strong, easy to separate, high yield effect

Inactive Publication Date: 2018-10-09
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of oxalyl chloride and aluminum trichloride in this reaction requires that the reaction must be carried out under strict anhydrous conditions. In addition, the hydrogen chloride released in the reaction also needs to be neutralized by an additional base. The use of glacial acetic acid as a solvent makes the reaction conditions more harsh, and the most important thing is that other substituents on the iminoaryl group except the ortho-hydroxyl group have not been proposed to have the same applicability.

Method used

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  • Benzofuranone/ naphthofuranone aryl imine compound and synthetic method thereof
  • Benzofuranone/ naphthofuranone aryl imine compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0028] (Z)-1-(4-methylphenylimine)naphtho[2,1-b]furan-2-one

[0029] Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-methylphenyl)glycine ethyl ester, solvent 1,2-dichloroethane into a 25mL oxygen-filled reactor 2.0mL. Heat to 120°C, keep stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 75%. 1 H NMR (400M, CDCl 3 ): δ8.96(d, J=8.4Hz, 1H), 8.06(d, J=8.8Hz, 1H), 7.88(d, J=8.0Hz, 1H), 7.68(t, J=7.6Hz, 1H ), 7.54-7.51 (m, 1H), 7.29 (d, J=8.8Hz, 1H), 7.26-7.22 (m, 2H). 7.09-7.07 (m, 2H), 2.40 (s, 3H).

Synthetic example 2

[0031] (Z)-1-(4-tert-butylphenylimine)naphtho[2,1-b]furan-2-one

[0032]Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-tert-butylphenyl) glycine ethyl ester, solvent 1,2-dichloroethyl Alkanes 2.0mL. Heat to 120°C, keep stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 82%. 1 H NMR (400M, CDCl 3 ): δ8.94(d, J=8.4Hz, 1H), 8.03(d, J=8.8Hz, 1H), 7.86(d, J=8.0Hz, 1H), 7.66(t, J=7.6Hz, 1H ),7.50(t,J=7.6Hz,1H),7.44(d,J=7.6Hz,2H),7.28-7.24(m,1H),7.14(d,J=7.6Hz,2H),1.36(s ,9H).

Synthetic example 3

[0034] (Z)-1-(4-methoxyphenylimine)naphtho[2,1-b]furan-2-one

[0035] Add 0.01mmol copper acetate, 0.3mmol acetic acid, 0.15mmol 2-naphthol, 0.1mmol N-(4-methoxyphenyl)glycine ethyl ester, solvent 1,2-dichloroethyl Alkanes 2.0mL. Heat to 120°C, keep stirring for 24h, stop the reaction, cool to room temperature, wash with saturated sodium chloride solution (25°C), extract with dichloromethane, dry, and distill off the solvent under reduced pressure, the crude product is separated by column chromatography (washing Removal agent: petroleum ether / dichloromethane) to obtain the target product with a yield of 80%. 1 H NMR (400M, CDCl 3 ): δ8.99(d, J=8.4Hz, 1H), 8.03(d, J=8.8Hz, 1H), 7.88(d, J=8.4Hz, 1H), 7.68(t, J=7.6Hz, 1H ), 7.52(t, J=7.6Hz, 1H), 7.34-7.26(m, 3H), 6.97(d, J=8.8Hz, 2H), 3.09(s, 3H).

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Abstract

The invention provides a benzofuranone / naphthofuranone aryl imine compound, and a novel method for synthesizing the benzofuranone / naphthofuranone aryl imine compound by using one-pot method of N-aryl glycine derivatives and phenol or 2-naphthol compounds under the condition that copper catalyzes the oxidation of oxygen. The method has the characteristics of strong functional group compatibility(for example, the method is suitable for alkyl, alkoxy, phenyl and sulfur-containing nitrogenous groups), simple reaction conditions, easily separated target products, and high yield. The method avoids the use of benzene or glacial acetic acid as a solvent and oxalyl chloride as an acylation reagent, and solves problems that benzene and glacial acetic acid damage the environment and extra alkali needs to be added. Furthermore, the one-pot preparation and the use of oxygen as an oxidizing agent provide a more economical and environmentally friendly way for the synthesis of the novel benzofuranone / naphthofuranone aryl imine compound.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a benzo / naphthofuranone aryl imine compound and a synthesis method thereof. 【Background technique】 [0002] The molecular skeletons of benzo / naphthofuranone compounds and their derivatives are widely found in natural products, bioactive substances and functional materials, especially in organic synthetic dyes (Org.Lett.2007,9,2449–2451; Chem .-Eur.J.2008, 14, 376–381; Eur.J.Org.Chem.2006, 102, 3–1033; Bioorg.Med.Chem.Lett.2007, 17, 6354–6363). In the 1970s, the British ICI company first introduced dyes with a benzofuranone structure. This type of dye has excellent dyeing performance and its structure is completely different from the traditional heteropoly-fused ring color development system, and has received extensive attention from the dye industry ( Dyes Pigm, 1980, 1, 103-120; GB: 2068402, 1981-08-12; EP: 371223, 1990-06-06). [0003] Since the first artificial synthesis o...

Claims

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Application Information

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IPC IPC(8): C07D307/92C07D307/82
CPCC07D307/82C07D307/92
Inventor 周永波刘龙董建玉尹双凤
Owner HUNAN UNIV
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