Preparation method for phenanthridine derivative

A derivative, phenanthridine technology, applied in the field of organic synthesis, can solve the problems of practical application difficulties, high reaction temperature, long time, etc., and achieve the effects of strong designability, simple post-processing, and easy operation

Inactive Publication Date: 2012-12-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The steps of the above preparation method are relatively simple, but the strong acid trifluoroacetic acid needs to be used in the preparation process, which is highly corrosive, expensive, and the reaction temperature is high and the time is long
[0013] In summary, the methods reported so far for the preparation of phenanthridine derivatives either have long routes and cumbersome steps, or use expensive or toxic reagents, making practical application difficult

Method used

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  • Preparation method for phenanthridine derivative
  • Preparation method for phenanthridine derivative
  • Preparation method for phenanthridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-8

[0041] Add catalyst, oxidizing agent, acid, 2-aminobiphenyl compound (II), olefin compound (III) and organic solvent 2ml in the round bottom flask of 10ml according to the raw material ratio of Table 1, mix and stir evenly, according to the reaction of Table 2 The conditions were to stir the reaction in the air for a specified time. After the reaction was completed, it was filtered, mixed with silica gel, and purified by column chromatography (eluent was petroleum ether and ethyl acetate, volume ratio=10:1) to obtain the corresponding phenanthridine derivative Thing (I), reaction process is shown in the following formula:

[0042]

[0043] Table 1

[0044]

[0045] Table 2

[0046]

[0047] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, TFEtOH is trifluoroethanol, EtOH is ethanol, Ph-p-Me is p-methylphenyl, Ph-p-OMe is P-methoxyphenyl, Ph-p-Cl is p-chlorophenyl; R in formula (I-7) 3 For the addition of oxycarbonyl ethyl...

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Abstract

The invention discloses a preparation method for a phenanthridine derivative. The preparation method comprises the following steps of: adding a catalyst, an oxidant, acid, a 2-phenylaniline compound and an olefin compound into organic solvent; after reaction, carrying out post treatment to obtain the phenanthridine derivative, wherein the catalyst is a bivalent palladium catalyst. According to the preparation method for the phenanthridine derivative disclosed by the invention, the adoption of reagents with high toxicity and high corrosiveness is avoided. The preparation method has the advantages of environment friendliness, easiness in operation, higher yield and simplicity and convenience in post treatment. In addition, a substrate obtained by the method is strong in designability and can be used for designing to synthesize a compound with the required structure according to actual requirements, and thus stronger practicability is realized.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of phenanthridine derivatives. Background technique [0002] Phenanthridine (Phenanthridine) and its derivatives are very important polynitrogen heterocyclic rings, which have good antibacterial, antiviral, anticancer and antibacterial activities. It is an important core structure of 5-HT3 receptor antagonists. Currently Such drugs have been widely used as antiemetic agents in anticancer chemotherapy. [0003] At present, there are many reports on the biological activities of these compounds. Relevant foreign literatures include literature I (Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 1. mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives, by Andrea Cappelli, Maurizio Anzini, Salvatore Vomero, Laura Mennuni, Francesco Makovec, Edith Doucet, Michel Hamon, Giancarlo Bruni, Ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07F9/576
Inventor 张玉红梁尊俊鞠龙谢永居黄乐浩
Owner ZHEJIANG UNIV
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