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A kind of 5-substituted arylation/heterocyclic 8-amidoquinoline compound and its one-pot preparation method

A technology of quinoline and arylation, applied in the field of catalytic organic synthesis

Active Publication Date: 2020-05-05
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The presence of metal salts has a negative impact on subsequent coupling reactions.

Method used

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  • A kind of 5-substituted arylation/heterocyclic 8-amidoquinoline compound and its one-pot preparation method
  • A kind of 5-substituted arylation/heterocyclic 8-amidoquinoline compound and its one-pot preparation method

Examples

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Effect test

preparation example 1

[0019] Add 0.2mmol 8-(pivaloyl)aminoquinoline (R 1 =tert-butyl), 0.22 mmol NBS and 1 mL DMF, under a nitrogen atmosphere, the reaction was carried out at 160° C. for 24 h. After the completion of the reaction, the reaction was cooled to room temperature, then 0.3mmol phenylboronic acid, 0.4mmol sodium carbonate and 0.02mmol catalyst tetrakis (tri (2-methyl) phenyl) phosphine palladium were added under a nitrogen atmosphere, and the solvent dimethyl sulfoxide ( DMSO) (1mL) (1mL), reacted at 140°C for 6 hours, after the reaction, filtered, concentrated, and separated by column chromatography to obtain 5-phenyl-8-(pivaloyl)aminoquinoline, the yield was 83%.

preparation example 2

[0021] Add 0.2mmol 8-(pivaloyl)aminoquinoline (R 1 =Me), 0.22 mmol NIS and 1 mL DMF, under a nitrogen atmosphere, the reaction was carried out at 160° C. for 24 h. After the reaction was completed, the reaction was cooled to room temperature, then 0.3mmol phenylboronic acid, 0.4mmol sodium carbonate and 0.02mmol catalyst tetrakis (tri (4-methyl) phenyl) phosphine palladium were added under a nitrogen atmosphere, and the solvent dimethyl sulfoxide ( DMSO) (1mL), reacted at 140°C for 6 hours, after the reaction, filtered, concentrated, and separated by column chromatography to obtain 5-phenyl-8-(methylacetamido)quinoline with a yield of 78% .

preparation example 3

[0023] Add 0.2mmol 8-(pivaloyl)aminoquinoline (R 1 =n-octly), 0.22 mmol NCS and 1 mL DMF, under a nitrogen atmosphere, the reaction was carried out at 160° C. for 24 h. After the reaction was completed, the reaction was cooled to room temperature, then 0.3mmol phenylboronic acid, 0.4mmol sodium carbonate and 0.02mmol catalyst tetrakis(tri(4-tert-butyl)phenyl)phosphine palladium were added under a nitrogen atmosphere, and the solvent dimethyl sulfoxide was added (DMSO) (1mL), reacted under the environment of 140 ℃ for 6 hours, after the reaction was finished, filtered, concentrated, separated by column chromatography to obtain 5-phenyl-8-(n-octylacetamido) quinoline, the yield was 73%.

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Abstract

According to the present invention, through a first-step metal-free halogenation reaction, a 5-site substituted arylated / heterocyclic 8-amidoquinoline compound is selectively obtained through a direct coupling reaction with a boric acid compound without separation; in the absence of the metal in the first step, the subsequent reaction is not affected; an aminoquinoline compound, a halide and a boric acid compound are adopted as raw materials, a common metal is adopted as a catalyst, and a common organic solvent is adopted as a reaction solvent; and halogenations, an arylation one-pot reaction, and column chromatography are sequentially performed to obtain the 5-site substituted arylated / heterocyclic 8-amidoquinoline compound.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and specifically relates to a 5-position substituted arylation / heterocyclic 8-amidoquinoline compound and a preparation method thereof. 【Background technique】 [0002] Due to their important role in natural products and pharmaceutical industry, quinolines have been widely concerned by chemical researchers in recent years. The introduction of the aryl structure (-AR) or the heterocyclic structure (-hetero) makes the compound have special activity and has a great prospect of medicinal value. Since the last century, many classic synthetic methods have been reported one after another. At present, the more common method is to use precursor aniline and carbonyl compound or alkyne to carry out cycloaddition reaction and ring closure to prepare corresponding quinoline compounds. However, this kind of method requires pre-preparation of expensive multi-substituted precursor aniline, which req...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40C07D409/04C07D405/04
CPCC07D215/40C07D405/04C07D409/04
Inventor 邱仁华李优朱龙志尹双凤曹鑫
Owner HUNAN UNIV
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