Obtaining polyfunctional S-, N-derivatives of dicyclopentene and study of their antimicrobial properties
Year: 2024
Type: article
Abstract: Sulfur-and nitrogen-containing functional derivatives of dicyclopentene (tricyclo[5.2.1.02.6 ]dec-3-ene) was synthesized through successive stages of conversion of starting cycloolefin.Isomers of bromohydrin with a bridge structure were obtained by oxidative hydroxybromination in the presence of hydrogen peroxide and hydrobromic acid.It was established that hydroxybromination of dicyclopentene occurs "in situ" with the formation of a metastable intermediate containing an electrophilic oxygen atom.The latter interacts with the multiple bond of the substrate and promotes the formation of an intermediate oxirane fragment.the latter is converted into bromhydrin by eliminating a water molecule.In the second stage, by the condensation with pentane-1-thiol in the presence of anhydrous ZnCl 2 taken as a catalyst, a mixture of pentylthiotricyclodecanol isomers was synthesized without changing the structure of the original carbon.In the third stage, isomers of the corresponding sulfur-and nitrogen-containing dicyclopentene derivatives were obtained by triple condensation of alkylthiotricyclodecanol with formaldehyde and morpholine (or piperidine) using Mannich reaction.Optimal process conditions for each stage were found.The yields of the target productspentylthiotricyclo[5.2.1.02.6 ]decyl-hydroxymethylmorpholine (or piperidine) under these conditions were 85.0-89.0%.The synthesized compounds were tested as antimicrobial, anti-corrosion and anti-wear additives for "M-10" motor oil and "Azerol-5" cutting fluid emulsion.These compounds, containing tricyclic bridge structures, can be used as multifunctional additives for "M-10" oil and cutting fluids, ensuring their biostability.The results show that some synthesized compounds in amounts of 0.25-1.0%exhibit active protective properties.It was established that bactericidal and fungicidal activity of the compounds also depends on the structure and composition of substituents at the nitrogen and sulfur atoms Keywords: dicyclopentene, hydrogen peroxide, morpholine, piperidine, pentane-1-thiol, bactericidal propertiesVicinal amino alcohols with a cyclic structure and their derivatives are widely used in the synthesis of analogues of complex natural and biologically active compounds [1,2].Thus, it's known that there are some derivatives of vicinal amino alcohols with amino and hydroxyl groups among the currently used drugs, in particular, diphenhydramine, adrenaline, antibiotics -
Source: PPOR
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4400399990