Synthetic method of aryl sulfhydryl diazole derivative

Abstract

The invention discloses a synthetic method of an aryl sulfhydryl diazole derivative. The preparation method comprises the following steps: with 2,5-disubstituted oxadiazole and thiadiazole as raw materials, dissolving the raw materials in a certain amount of organic solvent, and adding a fluorinating agent to form a raw material system,; sealing the reaction device, fully replacing the gas in thedevice with N2, heating the reactant to reflux, adding a benzyne precursor by using an injector, performing a reaction for 5-6 hours; and after the reaction is finished, carrying out aftertreatment toobtain the aryl sulfhydryl diazole derivative. The reaction method is simple to operate, raw materials and reaction time are saved, the conversion rate and selectivity of the reaction are ideal, andcompared with the prior art, the environmental pollution is small, the operation is safe, and the method is a novel heterocyclic compound sulfydryl arylation reaction method. The method is applied toarylation reaction of sulfydryl on various oxadiazole and thiadiazole rings, but is not limited to preparation of aryl sulfydryl oxadiazole and thiadiazole.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a synthesis method of arylmercaptodiazole derivatives, more specifically to a reaction method for arylation of mercapto groups on oxadiazole and thiadiazole rings. Background technique [0002] Oxadiazoles and thiadiazoles are two important types of heterocyclic compounds, which have attracted much attention because of their unique five-membered polyheteroatom ring structure. Many oxadiazole and thiadiazole derivatives have excellent antibacterial, insecticidal, plant growth regulation and antiviral activities, and can also exert pharmacological effects such as anti-infection, anti-inflammation, anti-depression and anti-cancer. Derivatives formed by linking oxadiazole and thiadiazole to phenylmercapto have attracted attention in the fields of microbiology and pharmacy. Some studies have pointed out that the antimicrobial activity of phenylmercaptothiadiazole is a minimum inhibito...

AI Technical Summary

Problems solved by technology

The diazotization-halogenation reaction is also catalyzed by cuprous salts, and the diazonium salts have high temperature or the danger of explosion under impact. There are still many problems and defects in the operation of the diazotization reaction and product treatment, which need further improvement (Alemagna , A.; Bacchetti, T.; Beltrame, P.Tetrahedron1968,24,3209); other methods of introducing phenylmercapto and phenylene ether groups on the oxadiazole and thiadiazole rings, such as Grignard reagents, organic Zinc reagents and other organic reagents with cumbersome preparation process and high cost are not suitable for popularization and application due to harsh conditions (Yonova, Ivelina M. Journal of Organic Chemistry, 79(5), 1947-1953; 2014)

In summary, the phenylthiolation reactions of oxadiazoles and thiadiazoles are basically limited to the improvement of traditional coupling synthesis methods, such as the development of catalysts and the application of new thiolation reagents. The method can only be completed under the condition of high temperature and long time

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