Synthesis of Fused Compounds on the Basis of Chalcogen Chlorides and 2-Allylphenols

Мусалов, М. В.; Ishigeev, R. S.; Udalova, S. I.; Мусалова, М. В.; Kurkutov, E. O.; Хабибулина, А. Г.; Albanov, A. I.; Потапов, В. А.; Амосова, С. В.

doi:10.1134/s1070428018070114

Cited by 11 publications

(4 citation statements)

References 21 publications

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“…It is known that the α CÀ H position of β-naphthol can be activated toward the electrophilic aromatic substitution by the presence of a base, [34,35] for this reason we explored different bases that were grinded in a mortar with 1 and reacted with a solution of Se 2 Cl 2 prepared in situ by the reaction of elemental selenium with SO 2 Cl 2 [36] that is known to generate the selenium monochloride Se 2 Cl 2 and the tetrachloride SeCl 4 via a dispro-portionation reaction that is very sensitive to solvent donor strength (Scheme 1). [37,38] Results of the preliminary screening are reported in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Vibrational and Electronic Circular Dichroism Study of Chiral Seleno Compounds Prepared from a Naphthol Based Diselenide

et al. 2022

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Base induced activation of β‐naphthol toward the electrophilic aromatic substitution has been used for the synthesis of the unprecedented 1,1’‐diselanediylbis(naphthalen‐2‐ol) fully characterized by means of NMR and X‐Ray analysis. Its reactivity was studied and the synthesis of novel chiral selenium containing heterocycles was discovered. Chiroptical methods (VCD and ECD) were successfully used to define their absolute configuration and these results represent the first example reported for organoselenium derivatives.

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Section: Resultsmentioning

confidence: 99%

Vibrational and Electronic Circular Dichroism Study of Chiral Seleno Compounds Prepared from a Naphthol Based Diselenide

et al. 2022

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“…Phenol derivatives containing various functional groups and heteroatoms in their structures are relevant and promising both in theoretical and applied terms [1][2][3][4][5]. They can be used in various fields of technology as antioxidant, anticorrosive, antimicrobial additives to oils and fuels, stabilizers of polymeric materials, analytical reagents, etc.…”

Section: Introductionmentioning

confidence: 99%

Study of the Condensation Reaction of 2-Allylphenol With Formaldehyde and Methylamine and the Functional Properties of the Obtained Products

Mehdiyeva¹,

Bayramov²,

Agayeva³

2023

AChJ

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By triple condensation of 2-allylphenol with formaldehyde and methylamine (at a ratio of 1:1:1 and 1:2:1 mol, at 800C for 3 hours) a number of compounds (I-III) of various structures was prepared. It has been established that, depending on the ratio of the taken reagents, compounds of various structures are formed. By the reaction of compound I - 8-allyl-substituted 1,3-benzoxazine with HBr quaternary ammonium salt (IV) was obtained. Antimicrobial activity of 8-allyl-substituted 1,3-benzoxazine (I) and ammonium salt (IV) against microorganisms: Staphylococcus aureus NCTC 6571, Staphylococcus aureus ATCC®25923, Escherichia coli ATCC®25922, Candida albicans NSTC-3255/ATCC2091, Shigella flexneri ATCC®12022, Salmonella enterica ATCC®13076, and Aspergillus niger (aquatic isolate) was studied. It was found that compounds I and IV at a concentration of 30 mg/L in comparison with the references (amoxicillin and fluconazole) have the highest bactericidal and fungicidal properties. By thermal treatment of compound I cross-linked copolymer V was synthesized. While studying the thermal properties of copolymer V their sufficient thermal stability (up to ~4500C) was established. Copolymer V also has a sorption property for the extraction of uranyl ions from aqueous systems (the degree of extraction at pH 7 is ~70%, the sorption capacity – 178 mg/g). The structures of the obtained compounds were confirmed by IR and NMR spectroscopy

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“…Previously, we first introduced selenium dihalides in organic synthesis for preparation of organoselenium compounds [ 59 , 60 , 61 ] and used these reagents for selenocyclofunctionalization reactions [ 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 ]. The application of selenium dihalides in selenocyclofunctionalization allows to carry out two heterocyclization processes in one molecule and to obtain selenides containing two heterocyclic moieties [ 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 ].…”

Section: Introductionmentioning

confidence: 99%

A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products

et al. 2021

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The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO3 affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90–92% yield. Similar sulfides were obtained in 70–72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91–92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed.

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Synthesis of Fused Compounds on the Basis of Chalcogen Chlorides and 2-Allylphenols

Cited by 11 publications

References 21 publications

Vibrational and Electronic Circular Dichroism Study of Chiral Seleno Compounds Prepared from a Naphthol Based Diselenide

Vibrational and Electronic Circular Dichroism Study of Chiral Seleno Compounds Prepared from a Naphthol Based Diselenide

Study of the Condensation Reaction of 2-Allylphenol With Formaldehyde and Methylamine and the Functional Properties of the Obtained Products

A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products

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