Method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds

A technology of quinolines and 5-c, which is applied in the direction of organic chemistry, can solve the problems of time-consuming and labor-consuming preparation process, low product yield, high reaction temperature, etc., and achieve low catalyst consumption, high yield and post-treatment simple effect

Active Publication Date: 2020-04-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Based on the above, it can be found that the preparation methods of the existing [1,2,3]-triazolo[4,5-c]quinoline compounds generally have the following disadvantages, such as: serious safety hazards, high reaction temperature , The preparation process is time-consuming and labor-intensive, using a large amount of metal reagents, a large amount of three wastes, and the yield of some products is low, etc.

Method used

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  • Method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds
  • Method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds
  • Method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Example 1 Preparation of 4-phenyl-1H-[1,2,3]-triazolo[4,5-c]quinoline

[0033]In a 15mL reaction test tube, add 3-(2-aminophenyl)-1-phenyl-2-ynyl-1-one (0.110g, 0.5mmol), azidotrimethylsilane (0.064g, 0.55mmol), tetrabutylammonium fluoride (0.007g, 0.025mmol) and 5mL DMF, stirred magnetically at 25°C for 6 hours. TLC detected that the starting material had been completely converted. Add 10mL of water to dilute, and extract three times with ethyl acetate (each dosage is 5mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo to recover ethyl acetate, and the crude product was purified by column chromatography (volume ratio 5:1 petroleum ether / ethyl acetate as eluent) to obtain 4-phenyl- 0.110 g of 1H-[1,2,3]-triazolo[4,5-c]quinoline, yield 90%, the product is a white solid, melting point: 216.2°C. 1 H NMR (DMSO-d 6 ,500MHz): δ=16.97(s,1H),8.86(s,1H),8.43(d,J=8.0Hz,1H),8.26(d,J=8.0Hz,1H),7.85-7.90(m, 1H),7.77-7.82(m,1H),...

Embodiment 2-23

[0035] Using tetrabutylammonium fluoride as catalyst, 1H-[1,2,3]-trimethylsilane was prepared by reacting different β-(2-aminophenyl)-α,β-ynones with azidotrimethylsilane Azolo[4,5-c]quinoline compounds, the experimental operation is the same as in Example 1, and the results are shown in Table 1.

[0036] Table 1 Different β-(2-aminophenyl)-α,β-ynones as raw materials and azidotrimethylsilane (TMS-N 3 ) reaction to prepare 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds

[0037]

[0038]

[0039] Characterization data of some products:

[0040] 4-(2'-methylphenyl)-1H-[1,2,3]-triazolo[4,5-c]quinoline (Example 2)

[0041] White solid, melting point: 225.4°C; 1 H NMR (DMSO-d 6 ,500MHz): δ=16.68(s,1H),8.45(d,J=7.75Hz,1H),8.20(d,J=8.40Hz,1H),7.81-7.86(m,1H),7.75-7.80( m,1H),7.70(d,J=7.38Hz,1H),7.36-7.47(m,3H),2.34(s,3H)ppm. 13 C NMR (DMSO-d 6 ,125MHz): δ=144.06,136.61,136.56,130.69,130.49,129.60,129.18,127.58,125.63,122.74,20.16ppm.HRMS(+ESI):m / z calculated for C 16 h ...

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Abstract

The invention discloses a method for preparing 1H-[1,2,4]triazole compounds. The method comprises the following steps: mixing beta-(2-aminoaryl)-alpha,beta-acetylenone (1), azidotrimethylsilane (2), afluorine-containing catalyst and a reaction solvent, reacting at 0-60 DEG C for 3-8 h, monitoring by TLC until the raw materials are completely converted, and carrying out post-treatment on the reacted solution to obtain the product (I). The cheap and easily available fluorine-containing reagent is used as a catalyst, the dosage of the catalyst is small, and no metal reagent is used, so post-treatment is simple, and the quality requirements of medicines and electronic materials are easily met; azidotrimethylsilane is used for replacing sodium azide to serve as an azido source, so toxicity issmall, safety is high, reaction conditions are mild, the reaction can be smoothly carried out at the room temperature, the substrate range is wide, and the yield is high.

Description

technical field [0001] The present invention relates to a preparation method of 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds, in particular to a β-(2-aminoaryl)-α,β -A method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds by the Click / dehydration cyclization tandem method of alkyne ketone and azidotrimethylsilane. Background technique [0002] [1,2,3]-Triazolo[4,5-c]quinoline is a new type of heterocyclic ring fused by 1,2,3-triazole and quinoline, which has great potential in the fields of medicine, materials and biology. Potential practical application value (Bioorg.Med.Chem.2019, 27, 3511-3531; J.Med.Chem.2014, 57, 5845-5859). In recent years, research and development of preparation methods for this fused heterocycle have received extensive attention. So far, four methods for the preparation of such compounds have been reported, including: [0003] (1) Document 1 (Eur.J.Org.Chem.2013,28,6246-6248) reported for the first time the synthesis of 1H-[1,2,3]-tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 孙楠杨寒胡信全胡宝祥
Owner ZHEJIANG UNIV OF TECH
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