Method for synthesizing a 1,3,5-triazine derivative

Abstract

A method for synthesizing a 1,3,5-triazine derivative specifically includes the following steps: dissolving a benzyl chloride compound and an amidine hydrochloride compound in an organic solvent, wherein the amount-of-substance ratio of the benzyl chloride compound to the amidine hydrochloride compound is 1:(1-2); adding an oxidizing agent and an alkaline medium, and stirring at 100-130 DEG C for12-24 hours for reaction to obtain a 1,3,5-s-triazine derivative; and subjecting the 1,3,5-s-triazine derivative to cooling, extracting, drying and column chromatography isolation to obtain a pure product. The method has the advantages that reaction conditions are mild, the reaction activity is high, the reaction yield reaches 90%, the product selectivity is high, and the substrate expansion rangeis wide; transition metals, especially precious metal compounds, are avoided in a catalytic system, the cost is low, the method is safe and convenient, and the reaction system has less environmentalpollution.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 1,3,5-triazine derivatives. Background technique [0002] Organic compounds with triazine ring as the parent and skeleton exhibit unique biological and pharmaceutical activities such as insecticidal, herbicidal, antibacterial and anticancer. In addition, the s-triazine skeleton can also be used as an intermediate in the synthesis of other nitrogen heterocyclic compounds, as a functional material, enzyme inhibitor, and protein-targeted inhibitor, etc. As early as 1900, Wheeler et al. reported that aliphatic hydrocarbon-based s-triazine derivatives were synthesized by polycondensation of alkyl imidate esters using nitrile and fatty alcohol as raw materials, but the reaction yield was very low. (Wheeler H.L. et al. Am. Chem. J, 1900, 135, 23.) [0003] In recent years, many documents have reported methods for synthesizing 1,3,5-s-triazine derivatives: for...

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Problems solved by technology

[0003] In recent years, many documents have reported methods for synthesizing 1,3,5-s-triazine derivatives: for example, Pan et al. used 2,4,6-trichloro-1,3,5-triazine and anhydrous toluene as Raw material, 2,4,6-tri-p-tolyl-1,3,5-triazine (Polymer Chemistry, 2014,5,3424-3431) was synthesized by Friedel-Crafts reaction catalyzed by methane-sulfonic acid, the bottom of the reaction The raw materials are expensive and difficult to obtain, and the post-processing time is long

In 2015, Chen and Zhang et al reported the synthesis of 1,3,5-triazine derivatives through the dehydrogenation of benzamidine hydrochloride and alcohols using cheap copper acetate as a catalyst (Organic&biomolecular chemistry, 2015, 13,6723-6727), but this reaction requires metal catalysts and ligands to promote the reaction, the reaction steps are cumbersome and do not meet the theme of green development

In 2016, the Bhanage group reported the synthesis of s-triazine derivatives from benzylamine and N-substituted benzylamine and amidines in PEG-600, using cheap and easy-to-obtain oxygen molecules as oxidants, and s-triazines can be synthesized in good yields (Green chemistry, 2016, 18, 144-149), but the reaction needs to be carried out under an oxygen atmosphere, and the reaction operation is complicated

[0004] However, there are some defects in the above-mentioned various methods, such as expensive substrate raw materials, complicated reaction steps, harsh conditions, low yield, difficult post-treatment, use of some toxic solvents, especially the use of some Transition metal catalysts, high price, strong toxicity and dependence on highly toxic solvents severely restrict its industrial application in many fields

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