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Preparation method for formylated heterocyclic derivative

A derivative and formylation technology, which is applied in the field of preparation of formylated heterocyclic derivatives, can solve the problems of large equipment requirements, harsh conditions, high energy consumption, etc., and achieve short reaction time, mild conditions and high yield Effect

Active Publication Date: 2018-10-12
HARBIN INST OF TECH
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  • Claims
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Problems solved by technology

[0005] The purpose of the present invention is to solve the problem that the synthesis of formylated heterocyclic derivatives requires a high-temperature heating system, high energy consumption, harsh conditions, large requirements for equipment, and low yield, and to provide a formylated heterocyclic derivative method of preparation

Method used

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  • Preparation method for formylated heterocyclic derivative
  • Preparation method for formylated heterocyclic derivative
  • Preparation method for formylated heterocyclic derivative

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specific Embodiment approach 1

[0014] Specific embodiment 1: The preparation method of a formylated heterocyclic derivative in this embodiment is to dissolve the heterocyclic derivative, 2,2-ethoxyacetic acid, oxidizing agent and alkali in an organic solvent at room temperature, mix Uniform, then pass nitrogen gas for 25-35min, and then put it under the light of blue LEDs light to complete the reaction, then add acid to catalyze hydrolysis, adjust the pH to neutral, and then separate and purify through silica gel column chromatography to obtain the formylated hetero Ring derivatives; the molar ratio of heterocyclic derivatives, 2,2-ethoxyacetic acid, oxidizing agent and base is 1:5-8:2:2, and the molar volume ratio of heterocyclic derivatives and organic solvents is 1mmol: 10 -20mL;

[0015] Wherein the structural formula of the heterocyclic compound containing N structure is:

[0016] The structural formula of 2,2-ethoxyacetic acid is:

[0017] This embodiment is a one-step method for synthesizing di...

specific Embodiment approach 2

[0018] Specific embodiment 2: The difference between this embodiment and specific embodiment 1 is that the heterocyclic derivatives are quinoline compounds, isoquinoline compounds, quinoxaline compounds, pyridine compounds, imidazole compounds, benzimidazole compounds, Benzothiazole compounds, phenanthridine compounds, or natural product caffeine. Others are the same as the first embodiment.

specific Embodiment approach 3

[0019] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that the organic solvent is dichloromethane, acetonitrile, tetrahydrofuran or dimethyl sulfoxide. Others are the same as those in Embodiment 1 or 2.

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Abstract

The invention discloses a preparation method for a formylated heterocyclic derivative, and relates to the preparation method for the formylated heterocyclic derivative. The purpose of the invention isto solve the problems that current synthesis of a formylated heterocyclic derivative requires a high-temperature heating system, energy consumption is high, conditions are harsh, requirements on equipment are high, and a yield is low. The method comprises the following steps: dissolving a heterocyclic derivative, 2,2-ethoxyacetic acid, an oxidant and an alkali into an organic solvent at room temperature, performing uniform mixing, introducing a nitrogen gas for 25-35 min, placing the mixed material under a blue LED lamp, performing a complete illumination reaction, adding an acid, performingcatalytic hydrolysis, adjusting the pH to be neutral, and performing chromatography separation and purification by using a silica gel column, so as to obtain the formylated heterocyclic derivative. According to the method disclosed by the invention, the reaction can be performed at normal temperature and normal pressure, the reaction conditions are mild, the yield can reach 80%, and the method hasthe advantages of simple operation, no pollution, safety, environmental protection and low costs; and the method is used in the field of organic synthesis.

Description

technical field [0001] The invention relates to a preparation method of formylated heterocyclic derivatives. Background technique [0002] N-containing heterocycles and aldehyde-ketone skeletons are widely found in biologically active natural products and drug molecules. Due to its unique nitrogen-oxygen heterocycle structure, it is also an important raw material intermediate for many chemical products and other natural products. For example, by formylation modification of the natural product caffeine. According to literature reports, various important chemical raw material intermediates, such as typical natural products of compounds 1-4, can be obtained through a series of transformation reactions. Therefore, the synthesis of formylated heterocyclic derivatives has received extensive attention from chemists. [0003] [0004] At present, there are not many reports on the synthesis of formylated heterocyclic derivatives, and most of the existing synthesis methods use hi...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07D217/16C07D215/14C07D221/12C07D241/42
CPCC07B41/06C07D215/14C07D217/16C07D221/12C07D241/42
Inventor 杨超贾伟苟宝权
Owner HARBIN INST OF TECH
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