Imidazo heterocyclic azo derivative and preparation method and application thereof

A technology of heterocyclic azo and imidazo, applied in the field of imidazo heterocyclic azo derivatives and preparation thereof, can solve the problems such as complicated coupling reaction process, not too acidic, lowering the temperature of decomposition of diazonium salts, etc. The effect of excellent fluorescent properties

Active Publication Date: 2016-06-29
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are some shortcomings in the above-mentioned classic diazonium salt coupling preparation method. One is that there are certain restrictions on the substrate, that is, the heterocyclic ring should be connected with an amino group, because only when the substrate is connected with an amino group, the corresponding diazotization reaction can occur; The second is that the diazotization reaction is generally carried out at low temperature, because the low temperature can reduce the temperature at which the diazonium salt decomposes; in addition, the diazotization reaction needs to consume a large amount of inorganic acid (usually sulfuric acid or hydrochloric acid), and the acid is used to generate nitrous acid. The main purpose is to stabilize the generated diazonium salt. If the amount of acid is insufficient, the generated diazonium salt will ea

Method used

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  • Imidazo heterocyclic azo derivative and preparation method and application thereof
  • Imidazo heterocyclic azo derivative and preparation method and application thereof
  • Imidazo heterocyclic azo derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of 6-phenyl-(5-phenylazo) imidazo[2,1-b]thiazole

[0028] The synthetic route is:

[0029]

[0030] Specifically include the following steps:

[0031] The compound of formula (a) above, the compound of formula (b) and t-BuONO were adjusted to a molar ratio of 1:1.2:1.5, wherein the compound of formula (a) was 2 mmol. The reaction system was stirred and reacted in 1,2-dichloroethane at 50° C. for 6 hours. Cool after the reaction is over, filter with a short silica gel column, and the filtrate is rotary evaporated to remove the solvent. The residue is chromatographed on a silica gel column, rinsed with petroleum ether, and detected by TLC. Dry to obtain the target product as a red powder, the solution is yellow, the yield is 85%, and the purity is 99.1% (HPLC).

[0032] The effective temperature range of the reaction temperature in the above preparation steps is 40-100°C, the yield at 40°C is 70%; the yield at 100°C is 58%.

[0033] Redsolid.85...

Embodiment 2

[0038] Example 2: Synthesis of 2-phenyl-(3-phenylazo) imidazo[1,2-a]pyridine

[0039] synthetic route:

[0040]

[0041] Specifically include the following steps:

[0042] The compound of formula (a) above, the compound of formula (b) and t-BuONO were adjusted to a molar ratio of 1:1.2:1.5, wherein the compound of formula (a) was 2 mmol. The reaction system was stirred and reacted in 1,2-dichloroethane at 50° C. for 6 hours. Cool after the reaction is over, filter with a short silica gel column, and the filtrate is rotary evaporated to remove the solvent. The residue is chromatographed on a silica gel column, rinsed with petroleum ether, and detected by TLC. Drying gave the target product as a yellow powder with a yield of 60% and a purity of 99.3% (HPLC).

[0043] The effective temperature range of the reaction temperature in the above preparation steps is 40-100°C, the yield at 40°C is 51%; the yield at 100°C is 36%.

[0044] Redsolid.60%yield.M.P.:155–156℃.

[0045]...

Embodiment 3

[0049] Example 3: Synthesis of 2-(5-phenylazo)imidazo[2,1-b]thiazol-6-yl-phenol

[0050] The synthetic route is:

[0051]

[0052] Specifically include the following steps:

[0053] The compound of formula (a) above, the compound of formula (b) and t-BuONO were adjusted to a molar ratio of 1:1.2:1.5, wherein the compound of formula (a) was 2 mmol. The reaction system was stirred and reacted in 1,2-dichloroethane at 50° C. for 6 hours. Cool after the reaction is over, filter with a short silica gel column, and the filtrate is rotary evaporated to remove the solvent. The residue is chromatographed on a silica gel column, rinsed with petroleum ether, and detected by TLC. Drying gave the target product as a yellow liquid in 76% yield and 99.3% purity (HPLC).

[0054] The effective temperature range of the reaction temperature in the above preparation steps is 40-100°C, the yield at 40°C is 63%; the yield at 100°C is 47%.

[0055] Redsolid.76%yield(48.6mg).M.P.:171–172℃.

...

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Abstract

The invention belongs to the field of organic synthesis and azo dyes and particularly discloses an imidazo heterocyclic azo derivative and a preparation method and application thereof. The imidazo heterocyclic azo derivative has a structural formula shown as in formula (1), wherein heterocyclic Het is one of pyridine, thiazole and pyrimidine; R is C1-C6 alkyl groups, or aryl groups containing F, Cl, Br, MeO, CN and NO2 or aryl groups that are acetyl-substituted; Ar is aryl groups containing F, Cl, Br, MeO, CN and NO2 or aryl groups that are acetyl-substituted. The preparation method of the invention is an economical, simple and environment-friendly green synthetic method, neither the addition of mass hydrochloric acid or sulfuric acid and nitrites nor the pre-preparation of diazonium salts is required in the method, and imidazo heterocyclic azo compounds are directly produced under the action of tert-butyl nitrites. The imidazo heterocyclic azo derivative prepared herein has good fluorescent properties and is useful in the fields such as fluorescent dyes, luminescent materials and bactericides.

Description

technical field [0001] The invention belongs to the field of organic synthesis and azo dyes, in particular to an imidazoheterocyclic azo derivative and its preparation method and application. Background technique [0002] Due to the azo group contained in the azo compound molecule, its dyeing performance is outstanding, and it is widely used in dyes and luminescent materials. And imidazoheterocyclic azo compounds have some characteristics of heterocyclic compounds. For example, imidazopyridine is an excellent drug lead skeleton with specific physiological activities and has a wide range of applications in pesticides and medicine, such as : In medicine, there are anti-anxiety drug alpitant, PDE inhibitor octoprenone, sedative zolpidem, etc.; in pesticides, imidazopyridine compounds can also be used as insecticides and fungicides (Li Zhaorui, imidazo[1, 2-a] Research on the synthesis method of pyridine derivatives and spiropyrrole compounds, master's degree thesis: P6); in ad...

Claims

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Application Information

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IPC IPC(8): C07D513/04C07D471/04C09K11/06C09B29/36
CPCC07D471/04C07D513/04C09B29/3647C09B29/3691C09K11/06C09K2211/1044
Inventor 汤日元徐莉江坤伦陈伟亮卓宝柳郑文旭李春远
Owner SOUTH CHINA AGRI UNIV
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