Preparation method of 6-H-phenanthridine compounds by one-pot process

A technology for 6-H-compounds, applied in organic chemistry, bulk chemical production, etc., can solve the problems of few reports on the synthesis of phenanthridine compounds, and achieve the effects of easy reaction, high yield and easy availability of raw materials

Inactive Publication Date: 2015-12-16
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
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Problems solved by technology

But for 6- H - There are few reports on the synthesis of phenanthridine compounds, especially the synthesis of such compounds by using simple and easy-to-obtain raw materials through the "one-pot" method has not been reported

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  • Preparation method of 6-H-phenanthridine compounds by one-pot process

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Embodiment Construction

[0023] The embodiments of the present invention will be further described below in conjunction with the accompanying drawings and specific examples, but the present invention is not limited to the following embodiments, and various changes may be made within the scope of knowledge of those skilled in the art.

[0024] A "one-pot method" for the preparation of 6- H -The method of phenanthridine compound, its reaction process is as follows:

[0025]

[0026] Among them, PG (ProtectedGroup) is a protecting group, including -Ms (methylsulfonyl), -Ts (p-toluenesulfonyl), -Ns (p-nitrobenzenesulfonyl) and -Ac (acetyl); substituent R 1 and R 2 Any of alkyl, alkoxy, acyl, nitro, cyano, and halogen.

[0027] The operation steps of synthetic representative compound 1:

[0028]

[0029] Will N -Protected arylamine, o-bromobromobenzyl compound, metal palladium catalyst, ligand and base are added in an organic solvent, reacted under heating and inert gas protection conditions, an...

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Abstract

The invention discloses a preparation method of 6-H-phenanthridine compounds by a one-pot process, which comprises the following steps: adding reactants N-protected arylamine and bromobenzyl bromide compounds into a solvent, adding a metal palladium catalyst, a ligand and an alkali, carrying out chemical reaction under heating and inert gas protective conditions, and after the reaction finishes, carrying out after-treatment to obtain the compound pure products. By using the simple accessible N-protected arylamine and the commercial accessible bromobenzyl bromide compounds as the raw materials, one-pot three-step cascade reaction is performed to obtain the 6-H-phenanthridine compounds. The method is simple to operate, and has the characteristics of simple after-treatment, higher yield and the like.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, in particular to 6- H -The preparation method of phenanthridine compound. Background technique [0002] Phenanthridine is an important class of fused heterocyclic compounds, and its structural units are widely found in natural products, pharmaceutical active molecules and organic functional materials, so the synthesis of such compounds has received more and more attention. The traditional method is to synthesize by Pictet-Spengler reaction, and other new methods have been developed in recent years, such as photocatalytic free radical reaction, microwave radiation cyclization reaction, oxidation reaction of 5,6-dihydrophenanthridine compound, etc. wait. But for 6- H There are few reports on the synthesis of phenanthridine compounds, especially the synthesis of such compounds by using simple and easy-to-obtain raw materials through a "one-pot" method has not been reported. The pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07D221/18
CPCY02P20/55C07D221/12C07D221/18
Inventor 韩文勇陈永正周晓建崔宝东向广艳
Owner ZUNYI MEDICAL UNIVERSITY
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