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New synthetic method for polysubstituted benzene compound

A synthesis method and compound technology are applied in the field of synthesis of polysubstituted benzene compounds, which can solve the problems of long reaction time and inability to recycle, and achieve the effects of short reaction time, good catalytic effect and mild reaction conditions.

Active Publication Date: 2009-06-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Before this reaction is given, the more ideal method of this type of compound in the prior art is that Dong Xue reported in J.Org.Chem2007,72,5443 with substituted malononitrile compounds and substituted nitrovinyl compounds as The raw materials are first catalyzed by triethylamine to generate key intermediates without separation and the above compounds are synthesized with an equivalent amount of sodium ethoxide in acetonitrile, but the reaction time is long (12 to 80 hours) and it is necessary to use an equivalent or even an excess of sodium alkoxide as a base to promote and the above-mentioned The inability of the reagents to be recycled is the shortcoming of this reaction

Method used

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  • New synthetic method for polysubstituted benzene compound
  • New synthetic method for polysubstituted benzene compound
  • New synthetic method for polysubstituted benzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of multi-substituted benzene

[0027] Product 3a: drop into raw material 1a (1.68 gram, 10 mmol) and raw material 2a (1.49 gram, 10 mmol) in dry 100mL two-necked flask, [Bmim]OH (2 mmol), 40 milliliters of ethanol are as solvent, The reaction mixture was warmed up to reflux and kept for reaction for 3 hours, cooled, and the organic solvent was recovered under reduced pressure. The residue was extracted three times with ethyl acetate (15 ml × 3), the combined ethyl acetate layer was concentrated and then subjected to silica gel column chromatography (n-hexane: acetic acid Ethyl ester=8:1) Yellow crystals were isolated.

[0028] The recovery of catalyst alkaline ionic liquid: the above-mentioned alkaline ionic liquid extracted by ethyl acetate is washed with ethyl acetate again, and then dried under vacuum to remove the organic solvent and can be reused many times. After repeated use for 5 times, a small amount of fresh The ionic liquid comp...

Embodiment 2

[0030] Embodiment 2: the preparation of multi-substituted benzene

[0031] Product 3b: Put raw material 1b (182 mg, 1 mmol) and raw material 2a (149 mg, 1 mmol) in a dry 25 mL two-necked flask, [Bmim]OH (0.5 mmol), and react without organic solvent The mixture was heated to 50°C for 6 hours, cooled, and the reaction solution was extracted three times with ethyl acetate (5 ml × 3). The combined ethyl acetate layer was concentrated and then subjected to silica gel column chromatography (n-hexane:ethyl acetate=8::1 ) to obtain yellow crystals.

[0032] Yellow crystal; mp197-198℃; yield: 86%. 1 HNMR (400MHz, CDCl 3 ): δ=7.42-7.49 (m, 5H), 7.26-7.34 (m, 4H), 6.80 (s, 1H), 5.88 (s, 2H), 2.43 (s, 3H); MS (EI): m / z(%)=330(35, M + +1), 329(100).HRMS(EI) calcd for C 20 h 15 N 3 o 2 ([M] + )329.1164, found: 329.1162.

Embodiment 3

[0033] Embodiment 3: the preparation of multi-substituted benzene

[0034] Product 3c: drop into raw material 1c (198 mg, 1 mmol) and raw material 2a (149 mg, 1 mmol) in a dry 25 mL two-necked flask, [Bmim]OH (0.1 mmol), 5 ml of ethanol as a solvent, The reaction mixture was heated to reflux and kept for 2.5 hours, cooled, and the organic solvent was recovered under reduced pressure. The residue was extracted twice with ethyl acetate (5 ml × 2), and the combined ethyl acetate layer was concentrated and then subjected to silica gel column chromatography (n-hexane: Ethyl acetate=8:1) isolated to obtain yellow crystals.

[0035] Yellow crystal; mp191-192℃; 1 H NMR (500MHz, CDCl 3 ): δ=7.55(dd, J 1 =2.0Hz,J 2 =6.8Hz, 2H), 7.43-7.45(m, 3H), 7.32-7.34(m, 2H), 7.02(dd, J 1 =2.0Hz,J 2 =6.8Hz, 2H), 6.78(s, 1H), 5.91(s, 2H), 3.87(s, 3H); 13 CNMR (125Hz, CDCl 3): δ=161.0, 149.3, 145.0, 143.0, 137.5, 133.7, 129.9, 129.2, 128.9, 128.8, 127.2, 126.3, 121.1, 116.2, 114.4, 92.3, 55.4....

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Abstract

The invention discloses a method for preparing a polysubstituted benzene compound. The structure of the polysubstituted benzene compound as is shown in formula (III). In the method, substituted malononitrile derivative with the structure as is shown in formula (I) and substituted nitroethylene compound with the structure as is shown in formula (II) are used as raw materials to act with each other under the temperature of 20-100 DEG C for 1-10h without solvent or in organic solvent under the catalysis of basic ionic liquid. The reaction liquid is separated and purified to obtain the polysubstituted benzene compound with the structure as is shown in the formula (III). The method for preparing the polysubstituted benzene compound has the advantages of temper reaction condition, simple operation, general high reaction yield, less pollutions, reusable catalyst, etc. And the method is a chemical synthetic method for the polysubstituted benzene compound with good promising prospect.

Description

(1) Technical field [0001] The invention relates to a new method for synthesizing multi-substituted benzene compounds. (2) Background technology [0002] Multi-substituted benzene compounds are important compounds in organic chemistry, natural product chemistry and polymer chemistry. At the same time, as the basic skeleton of many natural active compounds and the synthon of many pharmacologically active heterocyclic compounds, it is important in medicinal chemistry. also play an important role. [0003] The traditional methods for synthesizing multi-substituted benzenes are mainly substitution reactions, including electrophilic substitution (such as Friedel-Crafts alkylation and Friedel-Crafts acylation), nucleophilic substitution and coupling reactions. These methods often require harsh reaction conditions, expensive reagents or metal catalysts that are harmful to the environment, and have the disadvantages of cumbersome operation and low reaction regioselectivity. Theref...

Claims

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Application Information

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IPC IPC(8): C07C255/58C07C253/30
CPCY02P20/54Y02P20/582
Inventor 陈志卫苏为科丁锴
Owner ZHEJIANG UNIV OF TECH
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