{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T15:46:37Z","timestamp":1791906397116,"version":"4.3.4"},"reference-count":77,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2021,6,18]],"date-time":"2021-06-18T00:00:00Z","timestamp":1623974400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["19-33-90214 Aspiranty"],"award-info":[{"award-number":["19-33-90214 Aspiranty"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u201392% yield. Similar sulfides were obtained in 70\u201372% 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\u201392% 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.<\/jats:p>","DOI":"10.3390\/molecules26123729","type":"journal-article","created":{"date-parts":[[2021,6,18]],"date-time":"2021-06-18T11:19:20Z","timestamp":1624015160000},"page":"3729","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7638-8377","authenticated-orcid":false,"given":"Maxim V.","family":"Musalov","sequence":"first","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3151-6726","authenticated-orcid":false,"given":"Vladimir A.","family":"Potapov","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir A.","family":"Yakimov","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria V.","family":"Musalova","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arkady A.","family":"Maylyan","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sergey V.","family":"Zinchenko","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2874-3725","authenticated-orcid":false,"given":"Svetlana V.","family":"Amosova","sequence":"additional","affiliation":[{"name":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,6,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1038\/nrd1657","article-title":"The evolving role of natural products in drug discovery","volume":"4","author":"Koehn","year":"2005","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1021\/np068054v","article-title":"Natural products as sources of new drugs over the last 25 years","volume":"70","author":"Newman","year":"2007","journal-title":"J. Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"894","DOI":"10.1016\/j.drudis.2008.07.004","article-title":"Natural products in drug discovery","volume":"13","author":"Harvey","year":"2008","journal-title":"Drug Discov. Today"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"514","DOI":"10.1039\/C8NP00011E","article-title":"Recent trends in the structural revision of natural products","volume":"35","author":"Chhetri","year":"2018","journal-title":"Nat. Prod. Rep."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1111\/j.1747-0285.2008.00673.x","article-title":"Natural compounds: Leads or ideas? Bioinspired molecules for drug discovery","volume":"72","author":"Beghyn","year":"2008","journal-title":"Chem. Biol. Drug Design"},{"key":"ref_6","unstructured":"D\u2019Andrea, J. (1982). Ancient Herbs in the J. Paul Getty Museum Gardens, Getty Publications."},{"key":"ref_7","unstructured":"Tilford, G.L. (1997). Edible and Medicinal Plants of the West, Mountain Press Publishing."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Nieto, G. (2017). Biological Activities of Three Essential Oils of the Lamiaceae Family. Medicines, 4.","DOI":"10.3390\/medicines4030063"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"402","DOI":"10.1016\/j.foodchem.2016.04.111","article-title":"Antibacterial and Antifungal Activities of Thymol: A Brief Review of the Literature","volume":"210","author":"Marchese","year":"2016","journal-title":"Food Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.foodcont.2017.01.014","article-title":"Active Food Packaging Films with Synergistic Antimicrobial Activity","volume":"76","author":"Krepker","year":"2017","journal-title":"Food Control"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1016\/j.mrgentox.2007.01.011","article-title":"Investigation of the Mutagenic and Antimutagenic Effects of Origanum Compactum Essential Oil and Some of Its Constituents","volume":"629","author":"Mezzoug","year":"2007","journal-title":"Mutat. Res. Toxicol. Environ. Mutagen."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1016\/j.foodchem.2019.01.099","article-title":"Antifungal Effects of Thymol and Salicylic Acid on Cell Membrane and Mitochondria of Rhizopus Stolonifer and Their Application in Postharvest Preservation of Tomatoes","volume":"285","author":"Kong","year":"2019","journal-title":"Food Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"380","DOI":"10.3389\/fphar.2017.00380","article-title":"Pharmacological Properties and Molecular Mechanisms of Thymol: Prospects for Its Therapeutic Potential and Pharmaceutical Development","volume":"8","author":"Javed","year":"2017","journal-title":"Front. Pharmacol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6250","DOI":"10.1016\/j.bmc.2014.08.020","article-title":"Thymol and Eugenol Derivatives as Potential Antileishmanial Agents","volume":"22","author":"Bevilaqua","year":"2014","journal-title":"Bioorg. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.fct.2015.03.030","article-title":"In Vitro Toxicological Evaluation of Essential Oils and Their Main Compounds Used in Active Food Packaging: A Review","volume":"81","author":"Pichardo","year":"2015","journal-title":"Food Chem. Toxicol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/j.fct.2013.12.005","article-title":"Cytotoxicity and Morphological Effects Induced by Carvacrol and Thymol on the Human Cell Line Caco-2","volume":"64","author":"Pichardo","year":"2014","journal-title":"Food Chem. Toxicol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"122","DOI":"10.1016\/j.fct.2014.07.013","article-title":"Evaluation of the Mutagenicity and Genotoxic Potential of Carvacrol and Thymol Using the Ames Salmonella Test and Alkaline, Endo III- and FPG-Modified Comet Assays with the Human Cell Line Caco-2","volume":"72","author":"Maisanaba","year":"2014","journal-title":"Food Chem. Toxicol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"454","DOI":"10.2174\/1573407214666180503120222","article-title":"Thymol Chemistry: A Medicinal Toolbox","volume":"15","author":"Dheer","year":"2019","journal-title":"Curr. Bioact. Compd."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4893","DOI":"10.1007\/s11164-017-2919-2","article-title":"Design, synthesis, biological screenings and docking simulations of novel carvacrol and thymol derivatives containing acetohydrazone linkage","volume":"43","author":"Rajput","year":"2017","journal-title":"Res. Chem. Intermed."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2413","DOI":"10.1080\/00397910802138785","article-title":"Solid-Supported Synthesis of Bio-active Carvacrol Compounds Using Microwaves","volume":"38","author":"Narkhede","year":"2008","journal-title":"Synth. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1954","DOI":"10.1111\/cbdd.13366","article-title":"Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol","volume":"92","author":"Bkhaitan","year":"2018","journal-title":"Chem. Biol. Drug Design."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/S0378-1097(03)00890-5","article-title":"Susceptibility of methicillin-resistant staphylococci to oregano essential oil, carvacrol and thymol","volume":"230","author":"Nostro","year":"2004","journal-title":"FEMS Microbiol. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"512","DOI":"10.1016\/j.foodchem.2009.10.045","article-title":"Antimicrobial activities of some thymol derivatives from the roots of Inula hupehensis","volume":"120","author":"Zhao","year":"2010","journal-title":"Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"125","DOI":"10.2174\/1573407213666171115161626","article-title":"Synthesis of Thymol Derivatives as Potential Non-Irritant Antimicrobial and Insecticidal Agents","volume":"15","author":"Hazzaa","year":"2019","journal-title":"Curr. Bioactive Comp."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3989","DOI":"10.1021\/jf073272v","article-title":"Comparative Study on the Antioxidant and Biological Activities of Carvacrol, Thymol, and Eugenol Derivatives","volume":"56","author":"Mastelic","year":"2008","journal-title":"J. Agricult. Food Chem."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Piombino, C., Lange, H., Sabuzi, F., Galloni, P., Conte, V., and Crestini, C. (2020). Lignosulfonate microcapsules for delivery and controlled release of thymol and derivatives. Molecules, 25.","DOI":"10.3390\/molecules25040866"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2241","DOI":"10.1007\/s11164-016-2759-5","article-title":"Design, synthesis and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives","volume":"43","author":"Bagul","year":"2017","journal-title":"Res. Chem. Intermed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1423","DOI":"10.1080\/14786419.2017.1419232","article-title":"Antifungal activity of phenolic monoterpenes and structure-related compounds against plant pathogenic fungi","volume":"33","author":"Wang","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Pricopie, A.-I., Ionu, I., Marc, G., Arseniu, A.-M., Vlase, L., Grozav, A., Gaina, L.I., Vodnar, D.C., Pirnau, A., and Tiperciuc, B. (2019). Design and synthesis of novel 1,3-thiazole and 2-hydrazinyl-1,3-thiazole derivatives as anti-Candida agents: In vitro antifungal screening, molecular docking study and spectroscopic investigation of their binding interaction with bovine serum albumin. Molecules, 24.","DOI":"10.3390\/molecules24193435"},{"key":"ref_30","first-page":"1","article-title":"Synthesis and characterization of prodrugs of sulfonamides as an azo derivatives of carvacrol","volume":"10","author":"Koshti","year":"2018","journal-title":"Pharma. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.ica.2019.02.031","article-title":"Photodynamic inactivation of Enterococcus faecalis by conjugates of zinc (II) phthalocyanines with thymol and carvacrol loaded into lipid vesicles","volume":"489","author":"Sobotta","year":"2019","journal-title":"Inorg. Chim. Acta."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"547","DOI":"10.3109\/14756366.2013.823958","article-title":"Identification and Structure\u2013Activity Relationship Study of Carvacrol Derivatives as Mycobacterium Tuberculosis Chorismate Mutase Inhibitors","volume":"29","author":"Jeankumar","year":"2014","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1007\/s11101-015-9412-6","article-title":"Systematic evaluation of thymol derivatives possessing stereogenic or prostereogenic centers","volume":"15","author":"Lopez","year":"2016","journal-title":"Phytochem. Rev."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1080\/10426507.2012.740697","article-title":"Dithiophosphoric and Dithiophosphonic Acids and Their Derivatives on the Basis of Thymol: Synthesis and Antimicrobial Activity","volume":"188","author":"Cherkasov","year":"2013","journal-title":"Phosphorus Sulfur. Silicon Relat. Elements"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1374","DOI":"10.1002\/cbdv.201300392","article-title":"New thymol derivatives and cytotoxic constituents from the root of Eupatorium cannabinum ssp. asiaticum","volume":"11","author":"Chen","year":"2014","journal-title":"Chem. Biodivers."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1016\/j.ejmech.2016.05.017","article-title":"Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells","volume":"121","author":"Tatar","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6601","DOI":"10.1007\/s11164-017-3007-3","article-title":"Synthesis, biological activities and molecular docking simulation of hydrazone scaffolds of carvacrol, thymol and eugenol","volume":"43","author":"Rajput","year":"2017","journal-title":"Res. Chem. Intermed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"6390","DOI":"10.1039\/c2dt12225a","article-title":"Therapeutic potential of selenium and tellurium compounds: Opportunities yet unrealized","volume":"41","author":"Tiekink","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"6255","DOI":"10.1021\/cr0406559","article-title":"Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology","volume":"104","author":"Nogueira","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1473","DOI":"10.1021\/acs.jmedchem.9b01152","article-title":"Development and Therapeutic Potential of Selenazo Compounds","volume":"63","author":"Ruberte","year":"2020","journal-title":"J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"828","DOI":"10.1039\/B918778B","article-title":"5-Selenization of salicylic acid derivatives yielded isoform-specific 5-lipoxygenase inhibitors","volume":"8","author":"Yu","year":"2010","journal-title":"Org. Biomol. Chem."},{"key":"ref_42","first-page":"765","article-title":"Organic diselenides, ditellurides, polyselenides and polytellurides. Synthesis and reactions","volume":"Volume 4","author":"Rappoport","year":"2013","journal-title":"Patai\u2019s Chemistry of Functional Groups. Organic Selenium and Tellurium Compounds"},{"key":"ref_43","first-page":"1053","article-title":"Synthesis of biologically relevant small molecules containing selenium. Part B. Anti-infective and anticancer compounds","volume":"Volume 4","author":"Rappoport","year":"2013","journal-title":"Patai\u2019s Chemistry of Functional Groups. Organic Selenium and Tellurium Compounds"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4865","DOI":"10.1007\/s11033-014-3417-x","article-title":"Ebselen, a promising antioxidant drug: Mechanisms of action and targets of biological pathways","volume":"41","author":"Azad","year":"2014","journal-title":"Mol. Biol. Rep."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Woollins, J.D., and Laitinen, R.S. (2011). Selenium and Tellurium Chemistry. From Small Molecules to Biomolecules and Materials, Springer.","DOI":"10.1007\/978-3-642-20699-3"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Santi, C. (2014). Organoselenium Chemistry: Between Synthesis and Biochemistry, Bentham Science Publishers.","DOI":"10.2174\/97816080583891140101"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2125","DOI":"10.1021\/cr000426w","article-title":"Chemistry of Biologically Important Synthetic Organoselenium Compounds","volume":"101","author":"Mugesh","year":"2001","journal-title":"Chem. Rev."},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Lenardao, E.J., Santi, C., and Sancineto, L. (2018). New Frontiers in Organoselenium Compounds, Springer International Publishing AG.","DOI":"10.1007\/978-3-319-92405-2"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1016\/S0040-4020(00)01033-4","article-title":"Recent advances in selenocyclofunctionalization reactions","volume":"57","author":"Petragnani","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2606","DOI":"10.2174\/1385272820666160614081513","article-title":"Electrophilic Selenocyclofunctionalization in the Synthesis of Biologically Relevant Molecules","volume":"20","author":"Divac","year":"2016","journal-title":"Curr. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.molstruc.2018.07.091","article-title":"An introduction to the kinetics of the triethylamine-mediated selenocyclofunctionalization of 4-pentenoic acid","volume":"1175","author":"Divac","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"9118","DOI":"10.1039\/C5OB01297J","article-title":"7-Endo Selenocyclization reactions on chiral 3-prenyl- and 3-cinnamyl-2-hydroxymethylperhydro-1,3-benzoxazine derivatives. A way to enantiopure 1,4-oxazepanes","volume":"13","author":"Nieto","year":"2015","journal-title":"Org. Biomolec. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"8854","DOI":"10.1021\/jo061547k","article-title":"Diastereoselective Synthesis of Enantiopure Morpholines by Electrophilic Selenium-Induced 6-exo Cyclizations on Chiral 3-Allyl-2-hydroxymethylperhydro-1,3-benzoxazine Derivatives","volume":"71","author":"Pedrosa","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_54","first-page":"395","article-title":"Selenocyclofunctionalization of \u03b2-ketoamides: Synthesis of substituted dihydrofurans","volume":"171\u2013172","author":"Stefani","year":"2001","journal-title":"Phosphorus Sulfur. Silicon Relat. Elements"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"6837","DOI":"10.1021\/acs.chemrev.5b00400","article-title":"Use of Bromine and Bromo-Organic Compounds in Organic Synthesis","volume":"116","author":"Saikia","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2751","DOI":"10.1021\/jo302676g","article-title":"Iodide-Catalyzed Halocyclization\/Cycloaddition\/Elimination Cascade Reaction","volume":"78","author":"Kloeckner","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1021\/acs.joc.7b02299","article-title":"Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of S-Allyl Thioimidate Salts","volume":"83","author":"Parker","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4392","DOI":"10.1021\/jo102440k","article-title":"Thia-, Aza-, and Selena[3.3.1]bicyclononane Dichlorides: Rates vs Internal Nucleophile in Anchimeric Assistance","volume":"76","author":"Accurso","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1023\/A:1024742119781","article-title":"Synthesis of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes","volume":"39","author":"Potapov","year":"2003","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1373","DOI":"10.1023\/B:RUJO.0000010549.08131.18","article-title":"New Methods for Preparation of Organoselenium and Organotellurium Compounds from Elemental Chalcogens","volume":"39","author":"Potapov","year":"2003","journal-title":"Russ. J. Org. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1070\/RCR4795","article-title":"Organoelement chemistry: Promising growth areas and challenges","volume":"87","author":"Abakumov","year":"2018","journal-title":"Russ. Chem. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1702","DOI":"10.1134\/S107042801411030X","article-title":"Regioselective synthesis of bis[(2,3-dihydro-1-benzofuran-2-yl)methyl]selenide","volume":"50","author":"Musalov","year":"2014","journal-title":"Russ. J. Org. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1035","DOI":"10.1134\/S1070428018070114","article-title":"Synthesis of Fused Compounds on the Basis of Chalcogen Chlorides and 2-Allylphenols","volume":"54","author":"Musalov","year":"2018","journal-title":"Russ. J. Org. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1134\/S1070363217020359","article-title":"Bis(1,3-dioxolan-2-ylmethyl)selenide","volume":"87","author":"Kurkutov","year":"2017","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1007\/s10593-017-2031-y","article-title":"Selenium dihalides: New possibilities for the synthesis of selenium-containing heterocycles","volume":"53","author":"Musalov","year":"2017","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1715","DOI":"10.1134\/S1070428016110312","article-title":"Effective synthesis of bis(1,4-dioxan-2-ylmethyl)selenide and selenoxide","volume":"52","author":"Potapov","year":"2016","journal-title":"Russ. J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1134\/S1070428016100304","article-title":"Reaction of selenium dihalides with 2-(allylsulfanyl)ethanol","volume":"52","author":"Musalov","year":"2016","journal-title":"Russ. J. Org. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2973","DOI":"10.1007\/s11172-015-1258-y","article-title":"Efficient method for the synthesis of bis(tetrahydro-2H-pyran-2-ylmethyl) selenide","volume":"64","author":"Potapov","year":"2015","journal-title":"Russ. Chem. Bull."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1134\/S1070428016030088","article-title":"Synthesis of new functionalized organoselenium compounds by heterocyclization of selenium dihalides with pent-4-en-1-ol","volume":"52","author":"Potapov","year":"2016","journal-title":"Russ. J. Org. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"18476","DOI":"10.1039\/C9NJ04707G","article-title":"A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation\u2013methoxylation reactions of selenium dihalides","volume":"43","author":"Musalov","year":"2019","journal-title":"New J. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"2258","DOI":"10.1134\/S1070428020120350","article-title":"Synthesis of Functional Dihydro-1,4-benzoxaselenines from Carvacrol Allyl Ether and Selenium Dihalides","volume":"56","author":"Musalov","year":"2020","journal-title":"Russ. J. Org. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1021\/op900324p","article-title":"Use of Diethoxymethane as a Solvent for Phase Transfer-Catalyzed O-Alkylation of Phenols","volume":"14","author":"Coleman","year":"2010","journal-title":"Org. Proc. Res. Develop."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"282","DOI":"10.1021\/ar50140a003","article-title":"Episulfonium ions: Myth and reality","volume":"12","author":"Smit","year":"1979","journal-title":"Acc. Chem. Res."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1080\/01961770308047977","article-title":"New Sulfenyl Chloride Chemistry: Synthesis, Reactions and Mechanisms toward Carbon-Carbon Double Bonds","volume":"24","author":"Harpp","year":"2003","journal-title":"Sulfur. Rep."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"548","DOI":"10.1070\/RC1977v046n06ABEH002155","article-title":"The Addition of Sulphenyl Chlorides to Unsaturated Compounds","volume":"46","author":"Rasteikiene","year":"1977","journal-title":"Russ. Chem. Rev."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"365","DOI":"10.24820\/ark.5550190.p010.351","article-title":"Regioselective syntheses of bis(2-haloalkyl) selenides and dihalo[bis(2-haloalkyl)]-\u03bb4-selanes from selenium dihalides and 1-alkenes, and the methoxyselenenylation reaction","volume":"iii","author":"Musalov","year":"2017","journal-title":"Arkivoc"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"4606","DOI":"10.1016\/j.tetlet.2011.06.071","article-title":"Reactions of selenium dichloride and dibromide with unsaturated ethers. Annulation of 2,3-dihydro-1,4-oxaselenine to the benzene ring","volume":"52","author":"Potapov","year":"2011","journal-title":"Tetrahedron Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3729\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:18:33Z","timestamp":1760163513000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3729"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,6,18]]},"references-count":77,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2021,6]]}},"alternative-id":["molecules26123729"],"URL":"https:\/\/doi.org\/10.3390\/molecules26123729","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,6,18]]}}}