Search

We improved the synthetic procedure for 3-(2-arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones and established their structure. The study of their esterase profile showed the absence of cholinesterase inhibition and the selectivity against carboxylesterase with micromolar activity exceeding the anticarboxylesterase activity of the diketone analog. Carboxylesterase inhibition data are consistent with molecular docking results. 3-(2-Arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones exhibit a high radical-scavenging effect in the ABTS test exceeding that of Trolox. [ABSTRACT FROM AUTHOR]

New N-substituted enamino ketones were synthesized by directed transformation of 3-acetyl- and 3-benzoyl-5,6,7,8-tetrafluoro-4H-chromen-4-ones by the action of highly basic primary amines as a result of opening of the pyranone ring and deacylation. The synthesizedN-hexyl and N-octyl derivatives were evaluated for fungistatic and bacteriostatic activities. [ABSTRACT FROM AUTHOR]

Azo coupling of fluorinated 1,3-diketones with 4-ethoxycarbonyl-1 H-imidazole-5-diazonium chloride led to the formation of 4-hydroxy-4-polyfluoroalkyl-1,4-dihydroimidazo[5,1- c][1,2,4]triazines. According to the 1H and 19F NMR data, these compounds in solution give rise to ring-chain tautomerism via opening of the C4-N5 bond, which is especially characteristic of dihydroimidazotriazines with a polyfluoroalkyl substituent longer than trifluoromethyl group. [ABSTRACT FROM AUTHOR]

Fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones react with methylamine in different ways, depending on the substrate structure. Arylhydrazones having a short fluoroalkyl substituent (RF = CF3, HCF2CF2) react at the carbonyl group adjacent to the nonfluorinated substituent to give 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1-ones. Arylhydrazones with a long-chain fluoroalkyl group (RF = C3F7 and longer) and a bulky nonfluorinated group take up methylamine molecule at the carbonyl group linked to the fluorinated substituent, and the subsequent haloform reaction yields N-methyl-2-arylhydrazono-3-oxobutanamides. Both types of products are formed in reactions of methylamine with 1,2,3-triketone 2-arylhydrazones having a long fluoroalkyl group and methyl group at the other carbonyl group. Template condensation of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones with methylamine over Ni(II) template gives bis[3-alkyl(aryl)-1-polyfluoroalkyl-3-methylamino-2-aryldiazenylprop-2-en-1-onato- N,N′]-nickel(II), regardless of the size of the fluoroalkyl substituent. The same complexes and their copper analogs can be obtained by treatment of 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1-ones with the corresponding metal salts. [ABSTRACT FROM AUTHOR]

New fluoroalkyl-containing 2,2′-(biphenyl-4,4′-diyldihydrazono)bis(1,3-diketones) and 2,2′-(biphenyl-4,4′-diyldihydrazono)bis(3-oxopropionates) were synthesized by azo coupling of the corresponding 1,3-dicarbonyl compounds with biphenyl-4,4′-bis(diazonium) dichloride. Complexing ability of the obtained bis-hydrazones was studied, and new coordination compounds of the general formula M2L2 [where M = Ni(II), Cu(II); L = fluoroalkyl-containing 2,2′-(biphenyl-4,4′-diyldihydrazono)bis(1,3-diketone)] were obtained. [ABSTRACT FROM AUTHOR]

Polyfluorinated 2-arylhydrazono-3-oxocarboxylic acid esters react with o-phenylenediamine in neutral medium to give mainly the corresponding o-aminoanilides which can be converted into 1,5-benzodi-azepin-2-ones. In the reactions with ethyl 2-arylhydrazono-3-oxobutanoate and its 4,4-di- and 4,4,4-trifluoro derivatives, ethyl 2-(2-benzimidazolyl)-2-[(4-methylphenyl)hydrazono]ethanoate is also formed. [ABSTRACT FROM AUTHOR]

2-Arylhydrazono-1,3-diketones react with ethylenediamine to give, depending on the substituents, dihydro-1,4-diazepine derivative or N,N'-ethylenebis(1,3-aminovinyl ketones). Treatment of the latter with nickel(II) or copper(II) acetate results in formation of the corresponding metal chelates. Nickel complexes of N,N'-ethylenebis(1,3-aminovinyl ketones) can also be synthesized from 2-arylhydrazono-1,3-diketones and ethylenediamine on a metal template. Reactions of 2-arylhydrazono-3-oxo esters with ethylenediamine yield N,N'-ethylenebis(3-alkyl-2-arylhydrazono-3-oxopropionamides). Ethyl 2-arylhydrazonoacetoacetate reacts with ethylenediamine under mild conditions, affording ethyl 2-p-tolylazo-3-[2-(2-p-tolylhydrazono-1,3-dioxobutylamino)ethylamino]-2-butenoate. [ABSTRACT FROM AUTHOR]