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Synthetic method of acylated quinoline or isoquinoline derivatives

A technology for acylation of quinolines and synthetic methods, applied in the direction of organic chemistry, etc., can solve problems such as complex reactions, poor environmental protection, and harsh conditions, and achieve the effects of simple reaction conditions, wide application range, and simple and convenient operation

Active Publication Date: 2019-11-22
杭州量创科技咨询有限公司
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a new synthetic method for acylated quinoline or isoquinoline derivatives in order to solve the problems of complex reactions, harsh conditions and poor environmental protection in the existing synthesis methods of quinoline or isoquinoline derivatives

Method used

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  • Synthetic method of acylated quinoline or isoquinoline derivatives
  • Synthetic method of acylated quinoline or isoquinoline derivatives
  • Synthetic method of acylated quinoline or isoquinoline derivatives

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specific Embodiment approach 1

[0017] Specific embodiment one: the synthetic method of acylated quinoline or isoquinoline derivatives in this embodiment is implemented according to the following steps:

[0018] Under a nitrogen atmosphere, quinoline or isoquinoline and benzoylformic acid are used as reaction raw materials, persulfate is used as an oxidant, and a metal iridium complex is used as a visible light catalyst. The reaction is carried out under conditions, after the reaction is completed, the reaction system is filtered, concentrated and separated and purified to obtain acylated quinoline or isoquinoline derivatives, wherein the visible light catalyst is [Ir(ppy) 2 (dtbbpy)](PF 6 ) or 4CzIPN.

[0019] The structural formula of the present embodiment quinoline is: The structural formula of isoquinoline is: where substituent R 1 stands for H or Cl, R 2 Represents H, Cl or Me.

[0020] The reaction raw materials used in this embodiment can all be directly obtained commercially, and the oxidant...

specific Embodiment approach 2

[0021] Embodiment 2: This embodiment is different from Embodiment 1 in that the persulfate is ammonium persulfate, potassium persulfate or sodium persulfate. Other steps and parameters are the same as those in Embodiment 1.

specific Embodiment approach 3

[0022] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that the molar ratio of quinoline or isoquinoline to benzoylformic acid is 1:2. Other steps and parameters are the same as those in Embodiment 1 or Embodiment 2.

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Abstract

The invention discloses a synthesis method of an acylated quinoline or isoquinoline derivative, belongs to the field of organic synthesis, and aims to solve the problems of complicated reaction, severe conditions and low environmental friendliness in the conventional acylated quinoline or isoquinoline derivative synthesis method. The synthesis method comprises the following steps: under a nitrogenatmosphere, adding quinoline or isoquinoline and benzoyl formic acid which are used as reaction raw materials, persulfate used as an oxidant and a metal iridium compound used as a visible light catalyst into a reaction container together with an organic solvent for reaction under a visible light illumination condition, and at the end of the reaction, filtering, concentrating, separating and purifying a reaction system, thus obtaining the acylated quinoline or isoquinoline derivative. According to the synthesis method, under the nitrogen atmosphere, the reaction system is placed under a visible light source for illumination to realize reaction, so that the whole reaction process is safe and environmentally friendly, reaction conditions are simple, and operation steps are convenient; the synthesis method belongs to an environment-friendly chemical process.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing acylated (iso)quinoline derivatives. Background technique [0002] (Iso)quinoline derivatives are a common and important class of nitrogen heterocyclic compounds. (Iso)quinoline compounds containing different functional groups can exhibit various biological and pharmacological activities, such as antibacterial, antiviral, Anti-malarial and anti-tumor, etc., have been widely used in the fields of medicine and pesticides. (Iso)quinoline derivatives can be directly extracted from various natural products. Papaverine (papaverine) as shown in the following structural formula is extracted from poppy. It contains an isoquinoline skeleton structure and has an analgesic effect. In addition, such derivatives can also be obtained by chemical synthesis. As shown in the following structural formula, Neratinib is a small molecule tyrosine kinase inhibitor with a quin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/14C07D215/18
CPCC07D215/14C07D215/18
Inventor 赵亚婷吕延文贾伟夏吾炯
Owner 杭州量创科技咨询有限公司
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