Method for synthesizing quinolin-2-imide derivative

A synthesis method and technology of derivatives, applied in the field of synthesis of quinoline-2-imine derivatives, can solve problems such as poor tolerance of functional groups, complex and difficult to obtain raw materials, long reaction time, etc., and achieve scientific and reasonable synthesis methods, The effect of cheap catalyst and cheap raw materials

Active Publication Date: 2017-06-20
PEKING UNIV
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Problems solved by technology

Such as complex and difficult to obtain raw materials, long reaction time, low yield, poor tolerance of functional groups, etc.

Method used

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  • Method for synthesizing quinolin-2-imide derivative
  • Method for synthesizing quinolin-2-imide derivative
  • Method for synthesizing quinolin-2-imide derivative

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Experimental program
Comparison scheme
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Embodiment 3

[0041] Embodiment 3——compound shown in preparation formula IVc (R 1 = H, R 2 = R 3 = i Pr, R 4 = R 5 = 4-MeOC 6 h 4 ):

[0042]

[0043] At room temperature at 25°C, add 1.10 mmol of diphenyliodonium ion hexafluorophosphate, 1.20 mmol of bis(p-methoxyphenyl)acetylene and 0.15 mmol of cuprous trifluoromethanesulfonate to a 25 mL reaction tube, and add 3mL of dichloroethane was dissolved. Then add 1.0 mmol of N,N'-diisopropylcarbodiimide, and react at 100°C for 10 hours. The reaction system was dark red suspension. Filter and concentrate the reaction solution, decolorize and separate on a silica gel column, use petroleum ether: ethyl acetate=4:1 mixed solvent as eluent, obtain quinoline-2-imine derivative (IVc) 365mg (purity > 98%, Orange solid) in 82% isolated yield.

[0044] The NMR data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ): δ0.71(d, J=6.1Hz, 6H, CH 3 ), 1.67 (d, J=6.7Hz, 6H, CH 3 ),3.07-3.13(m,1H,CH),3.62(s,3H,CH 3 ),3.71(s,3H,CH 3 ),...

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Abstract

The invention discloses a method for synthesizing a quinolin-2-imide derivative. According to the method, the quinolin-2-imide derivative is prepared by using diaryl iodonium ions, carbodiimide, alkyne and a copper catalyst, the yield is relatively high, the synthesis method is scientific and reasonable, and thus, a universal method for synthesizing the quinolin-2-imide derivative with a variety of substituents by a three-component-reaction one-pot process is provided. According to the method, the raw materials are cheap and readily available, the catalyst is cheap, the applicable range is wide, the yield of separation is high, the regioselectivity is good, and the experimental facilities and operation are easy and feasible, so that further development and application are facilitated.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a series of nitrogen-containing heterocyclic compounds, especially a synthesis method of quinoline-2-imine derivatives. Background technique [0002] Quinoline compounds have been reported to have a wide range of biological activities. For example, the famous antimalarial drug "quinine sulfate" contains a quinoline ring. Especially a class of quinoline compounds with heteroatom substitution at the 2-position, such as quinoline-2-imine derivatives, etc. These molecules have been applied in a wide range of fields such as chemistry, biology, and pharmacy because of their high activity. . [0003] As described below, applications of quinoline-2-imine compounds in various fields have been reported. [0004] "Absorption and emission studies on pure and mixed J-aggregates of pseudoisocyanine. Chem. Phys. 2007, 341, 158" records that aryl-substituted quinoline-2-imine compounds can be u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38C07F7/08C07F7/10
CPCC07D215/38C07F7/0814
Inventor 张文雄迟樾严海涵席振峰
Owner PEKING UNIV
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