Facile Synthesis of Phenolic Derivatives, Containig Lactamomethyl Substituents

Abstract

In this work we suggest the new method for the synthesis of novel phenolic derivatives, containing lactamomethyl substituents. Oxidation processes of fuels and mineral oils lead to losing of their properties, so the search for new and effective inhibitors of these processes is very actuel. We suggest a facile system for lactamomethylation reaction. Heating in the water some of phenols (resorcinol, phloroglucinol, methylphloroglucinol, pyrogallol, salicylic, resorcilic and gallic acids) with N-hydroxymethyl derivatives of pyrrolidone, valerolactam, caprolactam and 4-phenylpyrrolidone in the presence of catalytic amounts of acetic acid led to the target compounds with nearly quantitative yields. Time of the reaction ranged 1.5-2 h. As the products have low solubility in water, in contrast with the reagents, filtration was used for their extraction. The advantages of this method are also that it is eco-friendly because of small amounts of wastes and low toxicity of the reagents and solvent, and cheapness of starting compounds. Eighteen novel compounds were obtained. The composition of target substances was determined by elemental analysis whereas the structures of the synthesized compounds were confirmed by FT-IR spectroscopy methods, 1H- and 13C-NMR spectroscopy. In IR spectra there are carbonyl group stretching vibrations peaks in lower frequencies (about 1600 cm-1) than expected due to the formation of inter- and intramolecular hydrogen bonds between this group and phenolic hydroxyl group.

Lactamomethylation of Phenols: Synthesis, In Silico Study of Reactivity and Possible Applications

“…Thus, for salicylic and βresorcylic acids there are several possible isomeric products. It was shown [21] that in case of these acids the lactamomethylation reaction took place in the third position (Scheme 3). As expected, the quantum-chemical calculations are in agreement with the experimental data (Scheme 4).…”

“…As a result, we have successfully synthesized alkylphenols derivatives (of 2,4-di-tertbutylphenol and thymol) with the fragments of pyrrolidone, valerolactam, caprolactam and 4phenylpyrrolidone [19]. In addition, we have obtained similar compounds for polyphenolic compounds, such as catechol and hydroquinone [20], and resorcinol, pyrogallol and phenolic acids [21].…”

Remote Stereoelectronic Effects in Pyrrolidone- and Caprolactam-Substituted Phenols: Discrepancies in Antioxidant Properties Evaluated by Electrochemical Oxidation and H-Atom Transfer Reactivity

“…The synthesis of the target compounds 1 – 11 was accomplished by the reported procedures. The data are the following: 1 , 1-(4-hydroxy-2,3,6-trimethylbenzyl)­pyrrolidin-2-one, 1.44 g (62%) of white powder; 2 , 1-(4-hydroxy-3,5-dimethylbenzyl)­pyrrolidin-2-one, 1.53 g (70%) of white powder; 3 , 1-(2,4-dihydroxybenzyl)­pyrrolidin-2-one, 1.66 g (80%) of white powder; 4 , 1-(2,4,6-trihydroxy-3-methylbenzyl)­pyrrolidin-2-one, 2.32 g (98%) of light brown powder; 5 , 1-(4-hydroxy-2,3,6-trimethylbenzyl)­azepan-2-one, 1.77 g (68%) of yellow powder; 6 , 1-(3,5-di-tert-butyl-4-hydroxybenzyl)­azepan-2-one, 2.32 g (70%) of white powder; 7 , 1-(2,4,6-trihydroxy-3-methylbenzyl)­azepan-2-one, 2.52 g (95%) of light brown powder; 8 , 1,1′-[(2,4,6-trihydroxy-1,3-phenylene)­di­(methylene)]­diazepan-2-one, 2.89 g (77%) of pale yellow powder; 9 , 1-(2,3,4-trihydroxybenzyl)­azepan-2-one, 1.98 g (79%) of white powder; 10 , 1-(3,5-di-tert-butyl-2-hydroxybenzyl)­azepan-2-one, 2.02 g (61%) of colorless crystals; 11 , 1-(4-hydroxy-3,5-dimethylbenzyl)­azepan-2-one, 1.78 g (72%) of pale yellow powder . The structures of the obtained compounds were supported by FT-IR, 1 H, and 13 C NMR.…”

Synthesis and Antioxidant Activity of 2-Amino-5-R-1,3,4-Oxadiazoles with Hindered Phenol Fragments

“…In continuation of our previous studies [24,25], in this work we combined in one structure a fragment of 2,6-di-tert-butylphenol and 2-alkyl/arylamino-1,3,4-oxadiazole and studied the antioxidant properties of the synthesized structures.…”