Synthesis of functionally substituted of 5-aryl-1,2,4-triazol-3-ones

doi:10.26565/2220-637X-2017-28-09

V. S. Tolkunov Litvinenko Institute of physico-organic chemistry and coal chemistry of NAS of Ukraine
O. V. Smirnova Litvinenko Institute of physico-organic chemistry and coal chemistry of NAS of Ukraine
A. S. Tolkunov Litvinenko Institute of physico-organic chemistry and coal chemistry of NAS of Ukraine
S. V. Tolkunov Litvinenko Institute of physico-organic chemistry and coal chemistry of NAS of Ukraine

DOI: https://doi.org/10.26565/2220-637X-2017-28-09

Keywords: cyclization, carbonylation, 5-aryl-1,2,4-triazol-3-ones, methyl carbazate, methyl arylcarboxyimidates, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II)

Abstract

A method for the preparation of variously substituted 5-aryl-1,2,4-triazol-3-ones, thermal cyclization of amidrazones obtained in situ from methyl benzimidates and methylcarbazate has been developed. An optimal procedure for the reduction of nitrophenyltriazolones with sodium sulfide in dioxane is proposed. The corresponding aminoaryltriazolones were obtained in 74-76% yields. Сarboxyderivatives of phenyltriazolones were synthesized by carbonylation of the corresponding bromophenyltriazolones with carbon monoxide in the presence of
[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) and triethylamine in methanol. It has been shown that the oxidation of tolyl triazolone with potassium permanganate in an alkaline medium is accompanied by the destruction of the triazolone ring and leads to terephthalic acid. The obtained aminophenyl- and carboxyphenyl-1,2,4-triazol-3-ones are of interest in terms of studying biological activity, as well as for further chemical modification.

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