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Preparation method of N-(2-hydroxy-5-methoxycarbonyl phenyl) acridone compound

A technology for methoxycarbonyl phenyl and compound, which is applied in the field of preparation of N-acridone compounds, can solve the problems of poor substrate adaptability, high reaction temperature, long reaction time and the like, and achieve sustainable development and utilization , The effect of convenient post-processing and short reaction time

Inactive Publication Date: 2014-09-17
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method of the reported N-arylacridone compound mainly contains the following two classes: (1) copper-catalyzed phenyl-(2-phenylaminophenyl) ketone intramolecular dehydrogenation to prepare N-aryl Acridones (Chem.Commun., 2012, 48 (8): 10678-10680; Chem. Eur. J., 2013, 19 (2), 460-464), however, such reactions require heavy metal catalysis and comparative Long reaction time and high reaction temperature, especially for substrates with phenolic hydroxyl groups in the molecule, no successful examples have been reported; (2) the insertion reaction of β-lactams using in situ generated benzyne intermediates to construct N -Arylacridone structural unit (Tetrahedron Lett., 2012, 53(37) 4994–4996), however, this kind of synthetic method has disadvantages such as poor reaction selectivity, low yield, many synthetic steps, and limited substrate adaptability.

Method used

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  • Preparation method of N-(2-hydroxy-5-methoxycarbonyl phenyl) acridone compound
  • Preparation method of N-(2-hydroxy-5-methoxycarbonyl phenyl) acridone compound

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Experimental program
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Embodiment 1

[0031] The preparation of N-(2-hydroxyl-5-methoxycarbonylphenyl) acridone comprises the following steps:

[0032] Step 1: Methyl 3-dehydroshikimate (0.41g, 2.2mmol), aniline (0.19g, 2.0mmol), p-toluenesulfonic acid (19.0mg, 0.1mmol), 5ml N,N-dimethylformamide Add to the microwave reaction vial at one time. The reaction system was reacted at 130° C. for 8 min in a microwave reactor.

[0033] Step 2: Potassium carbonate (0.83g, 6mmol), cuprous oxide (0.14g, 1mmol), o-iodobenzoic acid (0.50g, 2mmol) were added to the above system and reacted in a microwave reactor at 130°C for 5min. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solids were precipitated, filtered with suction, dried, and recrystallized with ethyl acetate-petroleum ether to obtain white crystals N- Phenyl-N-(2-carboxyphenyl)-2-hydr...

Embodiment 2

[0037] The preparation of 2-methyl-9-(2-hydroxyl-5-methoxycarbonylphenyl) acridone comprises the following steps:

[0038] Step 1: Methyl 3-dehydroshikimate (0.19g, 1.0mmol), p-methylaniline (0.11g, 1.0mmol), p-toluenesulfonic acid (19.0mg, 0.1mmol), 5ml N,N-dimethyl Acetamide was added to the microwave reaction vial at one time. The reaction system was reacted at 80°C for 20 min in a microwave reactor.

[0039] Step 2: Potassium carbonate (0.55g, 4mmol), cuprous oxide (0.14mg, 0.1mmol), o-iodobenzoic acid (0.25g, 1mmol) were added to the above system and reacted in a microwave reactor at 100°C for 15min. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solid precipitated, filtered with suction, dried, and recrystallized with ethyl acetate-ethanol to obtain light yellow crystals N -(4-methylphenyl)...

Embodiment 3

[0043] The preparation of 2-bromo-9-(2-hydroxyl-5-methoxycarbonylphenyl) acridone comprises the following steps:

[0044] Step 1: Methyl 3-dehydroshikimate (0.45g, 2.4mmol), p-bromoaniline (0.35g, 2.0mmol), formic acid (4.6mg, 0.1mmol), and 5ml dimethyl sulfoxide were added to the microwave reaction at one time in the bottle. The reaction system was reacted at 180° C. for 3 min in a microwave reactor.

[0045] Step 2: Potassium carbonate (0.83g, 6mmol), cuprous oxide (0.29g, 2mmol), o-iodobenzoic acid (0.50g, 2mmol) were added to the above system and reacted at 160°C for 5min in a microwave reactor. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solids were precipitated, filtered with suction, dried, and recrystallized with dichloromethane-petroleum ether to obtain white crystals N -(4-bromophe...

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Abstract

The invention discloses a preparation method of a N-(2-hydroxy-5-methoxycarbonyl phenyl) acridone compound, and the preparation method is as follows: condensation, isomerization and dehydration reaction of methyl-3-dehydroshikimate and an aryl amine compound under organic solvent, catalyst 1 and microwave condition to obtain a diarylamine intermediate; continuing addition of o-halogenated benzoic acid, an acid and catalyst 2 for reaction under microwave condition, then cooling, filtration and recrystallization to obtain a triarylamine intermediate; Friedel-crafts acylation reaction of the triarylamine intermediate for cyclization under the function of catalyst 3 to obtain the N-(2-hydroxy-5-methoxycarbonyl phenyl) acridone compound. The method has the advantages of simple operation, short reaction time, and easy postprocessing.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of N-(2-hydroxy-5-methoxycarbonylphenyl)acridone compounds. Background technique [0002] Acridones are an important class of nitrogen-containing heterocyclic organic compounds, and the related structure types are widely seen in biologically active molecules. For example: 8-methyl-1,3-dihydroxyacridone (structural formula Ⅰ) is a dihydroxy-substituted acridone compound, its anti-psoriasis activity is similar to dithranol, and it has been developed as an anti-silver Prospects of psoriasis drugs (Eur.J.Med.Chem., 2010, 45:3299-3310); 2-nitro-7-benzyloxyacridone (structural formula II) is a reversible inhibitor of cathepsin K and L Competitive inhibitors can be used as lead compounds of cathepsin competitive inhibitors (Eur.J.Med.Chem., 2012, 54:10-21). The structures of the above-mentioned molecules all have structural units of acridone. [0003] [0004]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/06
CPCC07D219/06
Inventor 邹永张恩生魏文徐田龙王德建黄桐堃
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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