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4-Aminoquinoline compound and preparation method thereof

A technology for aminoquinoline and compounds, applied in the field of 4-aminoquinoline compounds and their preparation, can solve the problems of low yield, limited sources of raw materials, complicated reaction process, etc., and achieve cheap raw materials, easy access to raw materials, and simple methods Effect

Active Publication Date: 2017-03-22
NORTHEAST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a 4-aminoquinoline compound and a preparation method thereof in order to solve the problems of limited source of raw materials, complex reaction process and low yield in the existing preparation method of 4-aminoquinoline compounds

Method used

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  • 4-Aminoquinoline compound and preparation method thereof
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  • 4-Aminoquinoline compound and preparation method thereof

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preparation example Construction

[0041] The present invention also provides a kind of preparation method of 4-aminoquinoline compound, the method comprises:

[0042] Step 1: Under acidic conditions, react dithioketenes with arylamines, or react enaminones, aryl isothiocyanates and halogenated hydrocarbons under alkaline conditions to obtain imino-N , S-ketene compound;

[0043] Step 2: The imino-N,S-ketal compound obtained in Step 1 is subjected to a self-cyclization reaction under the catalysis of a copper salt to obtain a 4-aminoquinoline compound.

[0044]Specifically, to prepare 4-aminoquinoline compounds with the structure of formula I, the preparation method preferably includes:

[0045] Under acidic conditions, dithioketal and arylamine react to generate imino-N, S-ketal compound; the molar ratio of said dithioketal to arylamine is preferably 1:(2- 3). The acidic conditions used preferably include Lewis acid, Bronsted acid, superacid, or acid modified by immobilization. More preferably boron triflu...

Embodiment 1

[0054] 1) Synthesis of imino-N,S-ketal compound 3

[0055]

[0056] Into a 50 mL round bottom flask equipped with a magnetic stirring device was added α-acetyl-α-carboethoxydithioketene 1a (2.62 g, 10 mmol), aniline 2a (2.79 g, 30 mmol), toluene 20 mL and trifluoro Boronium diethyl ether (0.37mL, 3mmol), stirred at 80 ° C, thin layer chromatography (TLC) to monitor the end of the reaction (5h), the reaction solution was carefully poured into saturated sodium chloride solution (20mL), dichloromethane (3 × 20mL) extraction, merging organic phases, drying over anhydrous sodium sulfate, suction filtration, vacuum distillation and other steps to obtain viscous solids, through silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =60:1) 2.39 g of a viscous yellow solid was obtained. The structure of the product was confirmed by NMR and mass spectrometry to be imino-N,S-ketal compound 3a, and the yield was 65%.

[0057] 2) Synthesis of 4-aminoquinoline compound 4a

[0058] ...

Embodiment 2

[0063] Replace the aniline in "Example 1" with 4-chloroaniline, replace 1a with benzylthio substituted dithioketene ketal, and other conditions are the same as "Example 1". The experimental results are shown in Table 1.

[0064]

[0065] Spectrum analysis 4b:

[0066] 1 H NMR (500MHz, CDCl 3 )δ8.47(s,1H),7.83(d,J=9.0Hz,1H),7.63(s,1H),7.55(d,J=9.0Hz,1H),7.20(d,J=8.5Hz, 2H), 6.81(d, J=8.5Hz, 2H), 4.32(q, J=7.0Hz, 2H), 2.77(s, 3H), 1.37(t, J=7.0Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ168.4, 157.6, 147.0, 147.0, 141.7, 131.6, 130.7, 130.7, 129.2, 127.9, 123.8, 120.7, 114.8, 61.9, 26.1, 14.0. HRMS (ESI-TOF) Calcd for C 19 h 17 Cl 2 N 2 o 2 (M+H) + 375.0662. Found 375.0655.

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Abstract

The invention provides a 4-aminoquinoline compound and a preparation method thereof, and belongs to the technical field of organic synthesis chemistry. The structural formula of the compound is represented by formula I or formula II. The invention also provides the preparation method of the 4-aminoquinoline compound. The method comprises the following steps: synthesizing imino-N,S-ketene from simple and easily available alpha-oxo ketene dithioacetal and amine under an acidic condition, or preparing the imino-N,S-ketene from enaminone, isorhodanate and halogenated hydrocarbon under an alkaline condition through a three-component reaction; introducing two different functional groups into the above obtained reaction system, and carrying out a catalytic ring closing reaction on the imino-N,S-ketene by using a cheap copper salt in order to synthesize diversified 4-aminoquinoline compounds. The method has the advantages of cheap and easily available raw materials, conciseness, mild reaction conditions, wide reaction applications, agile and changeable property, and avoiding of precious metal catalysis.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a 4-aminoquinoline compound and a preparation method thereof. Background technique [0002] 4-Aminoquinolines are an important class of nitrogen-containing heterocyclic compounds, which have important physiological activities such as antimalarial (Eur.J.Med.Chem.2014,85,147–178). For example, the most commonly used antimalarial drugs chloroquine, amoquine, mefloquine, ferroquine, etc. all have a framework structure of 4-aminoquinoline (Bioorg.Med.Chem.Lett.2010,20,1078–1080) . However, parasites have obvious resistance to common antimalarial drugs, which requires the continuous updating of antimalarial drugs. Therefore, the synthesis method of 4-aminoquinoline has attracted much attention, and the development of 4-aminoquinoline derivatives with new structures is of great significance. At present, the synthesis of 4-aminoquinoline derivatives is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/54C07D215/44
CPCC07D215/44C07D215/54
Inventor 潘玲刘群石楼
Owner NORTHEAST NORMAL UNIVERSITY
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