Imidazo heterocyclic azo derivative and preparation method and application thereof

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...

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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 easily self-couple with the unreacted arylamine to form a diazonium amino compound (theoretical research on diazotization and coupling reaction, Baoshan Teachers College Journal of the Chinese Academy of Sciences, 2002, 22 (2): 10-13); The third is that the coupling between diazonium salt and arylamine has a certain pH dependence, generally in weakly acidic medium, because acidic conditions can increase the water solubility of arylamine to make The reaction is carried out in the same phase, but the acidity should not be too large, and the aryl ammonium ion is not easily hydrolyzed into arylamine (new progress in the research on the synthesis strategy of aromatic azo derivatives, Organic Chemistry, 2013, 33, 444-457); the fourth part The coupling reaction process is cumbersome, such as some diazonium salts need to be separated to facilitate the next reaction

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