Abstract
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.
Highlights
Natural products and their derivatives play an important role in the discovery of new drugs [1,2,3,4,5]
The present work is devoted to regioselective synthesis of novel condensed functionalized organochalcogen compounds by chalcogenocyclofunctionalization reactions based on selenium dihalides, tellurium tetrahalides and sulfur dichloride and natural products, thymol (2-isopropyl-5-methylphenol) and carvacrol (5-isopropyl-2-methylphenol)
The aim of this research is to develop an efficient regioselective synthesis of novel condensed functionalized organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and natural products thymol (1) and carvacrol (2)
Summary
Natural products and their derivatives play an important role in the discovery of new drugs [1,2,3,4,5]. Many modern drugs have been developed from natural products, and synthesis of novel functionalized compounds based on natural products is promising in terms of the possible manifestation of biological activity. The present work is devoted to regioselective synthesis of novel condensed functionalized organochalcogen compounds by chalcogenocyclofunctionalization reactions based on selenium dihalides, tellurium tetrahalides and sulfur dichloride and natural products, thymol (2-isopropyl-5-methylphenol) and carvacrol (5-isopropyl-2-methylphenol). Thymol and carvacrol are isomeriC-Natural monoterpenoid phenols, found in essential oils of Thymus vulgaris (thyme) and Origanum vulgare (oregano) and extracted from various other kinds of plants. The thyme herb has been used in folk traditional medicine as a sedative and antiseptic since ancient times [6]. The ancient Greeks used it in their baths and burned it as incense in their temples, believing it was a source of courage. Its extract was used as a natural antibacterial gargle for sore throat and colds
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