5-cyano-8-acylaminoquinoline compound and preparation method thereof

A technology for amidoquinolines and compounds, applied in the field of 5-cyano-8-amidoquinolines and their preparation, to avoid metal catalysts and avoid competing reactions

Active Publication Date: 2021-12-10
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to overcome above-mentioned technical deficiency, provide a kind of 5-cyano-8-amidoquinoline compound and preparation method thereof, how to avoid using metal catalyst to prepare 5-cyanoquinoline compound in the prior art technical issues

Method used

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  • 5-cyano-8-acylaminoquinoline compound and preparation method thereof
  • 5-cyano-8-acylaminoquinoline compound and preparation method thereof

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preparation example Construction

[0018] This specific embodiment provides a kind of preparation method of 5-cyano group-8-amidoquinoline compound, comprises the following steps: in reactor, adds 8-amidoquinoline, tert-butyl isonitrile, iodosobenzene ( Abbreviated as PhIO), boric acid (chemical formula is B(OH) 3 ) and hexafluoroisopropanol (abbreviated as HFIP), then stirred and reacted at 60-70°C for 12-16h to obtain the 5-cyano-8-amidoquinoline compound;

[0019] The obtained 5-cyano-8-amidoquinoline compound is further purified, including: adding water to the prepared 5-cyano-8-amidoquinoline compound, and then adding ethyl acetate to extract 3 -4 times to obtain the organic phase, the organic phase is distilled under reduced pressure to obtain the crude product, and the crude product is separated and purified by column chromatography; the material ratio of the water and the 8-acylaminoquinoline is (75-100 ) mL:1mmol, the volume ratio of the water to the ethyl acetate is (1.5-2):1. The mol ratio of descr...

Embodiment 1

[0026] This embodiment proposes a 5-cyano-8-acetylaminoquinoline, which is prepared by the following steps: add 0.2mmol 8-acetylaminoquinoline, 0.6mmol tert-butylisonitrile, 0.3mmol Iodophenone, 0.6mmol boric acid and 2mL hexafluoroisopropanol, and then add a No. 5 magnet, pass condensed water through the condenser tube from bottom to top, and then stir the reactor at 60°C for 12h to obtain the 5-cyano -8-Acetamidoquinoline;

[0027] The obtained 5-cyano-8-acetylaminoquinoline was further purified, including: adding 15 mL of water to the obtained 5-cyano-8-acetylaminoquinoline, and then adding 10 mL of ethyl acetate to extract 3 times to obtain Organic phase, the organic phase was distilled under reduced pressure to obtain a crude product, and the crude product was separated and purified by column chromatography to obtain purified 5-cyano-8-acetylaminoquinoline with a yield of 50%.

[0028] combine figure 1 and 2 The structure of the product was determined by H NMR and C NM...

Embodiment 2

[0032] This embodiment proposes a 5-cyano-8-acetylaminoquinoline, which is prepared by the following steps: add 0.2mmol 8-acetylaminoquinoline, 0.7mmol tert-butylisonitrile, 0.35mmol Iodosobenzene, 0.7mmol boric acid and 2.5mL hexafluoroisopropanol, and then add a No. 5 magnet, pass the condensed water through the condenser tube from bottom to top, and stir the reactor at 65°C for 14h to obtain the 5- Cyano-8-acetylaminoquinoline;

[0033] The obtained 5-cyano-8-acetylaminoquinoline was further purified, including: adding 15 mL of water to the obtained 5-cyano-8-acetylaminoquinoline, and then adding 10 mL of ethyl acetate to extract 3 times to obtain Organic phase, the organic phase was distilled under reduced pressure to obtain a crude product, and the crude product was separated and purified by column chromatography to obtain purified 5-cyano-8-acetylaminoquinoline with a yield of 48.5%.

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Abstract

The invention discloses a 5-cyano-8-acylaminoquinoline compound and a preparation method thereof, belonging to the technical field of quinoline compounds. The preparation method of the 5-cyano-8-acylaminoquinoline compound comprises the following steps: adding 8-acylaminoquinoline, tert-butylisonitrile, iodosobenzene, boric acid and hexafluoroisopropanol into a reactor, and then carrying out stirring and reacting at a temperature of 60 to 70 DEG C to obtain the 5-cyano-8-acylaminoquinoline compound. The invention further discloses the 5-cyano-8-acylaminoquinoline compound prepared by using the preparation method disclosed by the invention. The preparation method does not use any metal catalyst, so the use of the metal catalyst is avoided.

Description

technical field [0001] The invention relates to the technical field of quinoline compounds, in particular to a 5-cyano-8-amidoquinoline compound and a preparation method thereof. Background technique [0002] Cyanide compounds are widely used in medicine, materials, dyes and other fields. Aryl nitrile polymer is a functional resin with excellent properties such as high temperature resistance and high strength. The TMS-1 type resin researched by Beijing Aeronautical Materials Research Institute is used for the pressing of carbon fiber composite CFRP plates. The cyanoquinoline structure-containing compound can be used in the field of drugs related to type 2 diabetes. It can be used as a glucokinase activator and in the preparation of type 2 diabetes drugs. [0003] In the prior art, there are mainly two kinds of synthetic methods for producing 5-cyanoquinoline compounds: one is to use Negishi coupling to synthesize 5-cyanoquinolines through halogen and palladium catalysts at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48
CPCC07D215/48Y02A50/30
Inventor 李栋汪亮张谦
Owner HUBEI UNIV OF TECH
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