{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T13:36:43Z","timestamp":1785159403284,"version":"3.55.0"},"reference-count":127,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2021,6,11]],"date-time":"2021-06-11T00:00:00Z","timestamp":1623369600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>3H-1,2-Dithiole-3-thiones are among the best studied classes of polysulfur-containing heterocycles due to the almost explosive recent interest in these compounds as sources of hydrogen sulfide as an endogenously produced gaseous signaling molecule. This review covers the recent developments in the synthesis of these heterocycles, including both well-known procedures and important novel transformations for building the 1,2-dithiole-3-thione ring. Diverse ring transformations of 3H-1,2-dithiole-3-thiones into various heterocyclic systems through 1,3-dipolar cycloaddition, replacement of one or two sulfur atoms to form carbon- and carbon-nitrogen containing moieties, and other unexpected reactions are considered.<\/jats:p>","DOI":"10.3390\/molecules26123595","type":"journal-article","created":{"date-parts":[[2021,6,11]],"date-time":"2021-06-11T12:44:37Z","timestamp":1623415477000},"page":"3595","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6609-4087","authenticated-orcid":false,"given":"Oleg","family":"Rakitin","sequence":"first","affiliation":[{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, Russia"},{"name":"Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,6,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2654","DOI":"10.1002\/cber.188401702203","article-title":"Ueber den Sulfovaleraldehyd","volume":"17","author":"Barbaglia","year":"1884","journal-title":"Chem. Ber."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"944","DOI":"10.1016\/S0891-5849(00)00175-1","article-title":"Chemoprotective 3H-1,2-dithiole-3-thione induces antioxidant genes in vivo","volume":"28","author":"Otieno","year":"2000","journal-title":"Free Radic. Biol. Med."},{"key":"ref_3","first-page":"835","article-title":"Lack of NQOl induction in human tumor cells is not due to changes in the promoter region of the gene","volume":"20","author":"Begleiter","year":"2002","journal-title":"Int. J. Oncol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1502","DOI":"10.1124\/mol.107.044347","article-title":"Abrogation of hyperosmotic impairment of insulin signaling by a novel class of 1,2-dithiole-3-thiones through the inhibition of S6K1 activation","volume":"73","author":"Bae","year":"2008","journal-title":"Mol. Pharmacol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1016\/j.bmc.2008.11.074","article-title":"Diaryldithiolanes and -isothiazoles: COX-1\/COX-2 and 5-LOX-inhibitory, OH scavenging and anti-adhesive activities","volume":"17","author":"Scholz","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5368","DOI":"10.1016\/j.bmc.2016.08.060","article-title":"Synthesis and biological evaluation of novel hydrogen sulfide releasing nicotinic acid derivatives","volume":"24","author":"Sun","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5995","DOI":"10.1039\/C4OB00830H","article-title":"Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents","volume":"12","author":"Wang","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2355","DOI":"10.1016\/j.bmcl.2016.03.012","article-title":"Synthesis and antitumor activity of ATB-429 derivatives containing a nitric oxide-releasing moiety","volume":"26","author":"Wang","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3093","DOI":"10.1128\/AAC.48.8.3093-3102.2004","article-title":"1,2-Dithiole-3-ones as potent inhibitors of the bacterial 3-ketoacyl acyl carrier protein synthase III (FabH)","volume":"48","author":"He","year":"2004","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1002\/jcb.240590815","article-title":"Oltipraz, a novel inhibitor of human-immunodeficiency-virus type-1 (hiv-1) replication","volume":"59","author":"Prochaska","year":"1995","journal-title":"J. Cell. Biochem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2640","DOI":"10.1016\/j.bmcl.2014.04.073","article-title":"Evaluation of the antiviral efficacy of bis[1,2]dithiolo[1,4]thiazines and bis[1,2]dithiolopyrrole derivatives against the nucelocapsid protein of the Feline Immunodeficiency Virus (FIV) as a model for HIV infection","volume":"24","author":"Asquith","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1609","DOI":"10.1093\/carcin\/19.9.1609","article-title":"Identification of dithiolethiones with better chemopreventive properties than oltipraz","volume":"19","author":"Maxuitenko","year":"1998","journal-title":"Carcinogenesis"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3005","DOI":"10.1016\/j.ejmech.2010.03.029","article-title":"Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity","volume":"45","author":"Chen","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","unstructured":"Bian, J., Cai, Z., and Wu, H. (2012). S-Danshensu Compound, Its Synthesis Method and Application for Protecting Sperm and Treating Male Infertility Diseases. (102417501 A), CN Patent."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1072","DOI":"10.1016\/j.neuint.2013.04.001","article-title":"Differential mechanisms underlying neuroprotection of hydrogen sulfide donors against oxidative stress","volume":"62","author":"Jia","year":"2013","journal-title":"Neurochem. Int."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1111\/j.1471-4159.2010.06580.x","article-title":"Hydrogen sulfide as a gasotransmitter","volume":"113","author":"Gadalla","year":"2010","journal-title":"J. Neurochem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1152\/physrev.00017.2011","article-title":"Physiological implications of hydrogen sulfide: A whiff exploration that blossomed","volume":"92","author":"Wang","year":"2012","journal-title":"Physiol. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Yamashita, Y., Tomura, M., and Zaman, M.B. (1998). Synthesis and properties of novel tetrathiafulvalene vinylogues. Chem. Commun., 1657\u20131658.","DOI":"10.1039\/a803531h"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6937","DOI":"10.1021\/jo990100r","article-title":"Electron acceptors of the fluorene series. Derivatives of 9-(1,2-dithiol-3-ylidene)-, 9-(1,3-dithiol-2-ylidene)-, and 9-(1,3-selenathiol-2-ylidene)fluorenes: Synthesis, intramolecular charge transfer, and redox properties","volume":"64","author":"Mysyk","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1487","DOI":"10.1016\/S0379-6779(00)01017-1","article-title":"Push-pull dithiole\u2014fluorene accepters as electron transport materials for holography","volume":"121","author":"Perepichka","year":"2001","journal-title":"Synth. Met."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"10401","DOI":"10.1039\/c1cc13511b","article-title":"Different donor-acceptor structures of dithiafulvalene-fused semiconducting polymers with different band gaps","volume":"47","author":"Hou","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_22","first-page":"569","article-title":"1,2-Dithioles","volume":"Volume 3","author":"Shinkai","year":"1996","journal-title":"Comprehensive Heterocyclic Chemistry II"},{"key":"ref_23","first-page":"893","article-title":"1,2-Dithioles","volume":"Volume 4","author":"Joule","year":"2008","journal-title":"Comprehensive Heterocyclic Chemistry III"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/S0065-2725(08)60396-7","article-title":"1,2-Dithiole-3-thiones and 1,2-dithiol-3-ones","volume":"31","author":"Pedersen","year":"1982","journal-title":"Adv. Heterocycl. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1080\/01961779508048738","article-title":"1,2-Dithiole-3-thiones and 1,2-dithiol-3-ones","volume":"16","author":"Pedersen","year":"1995","journal-title":"Sulfur Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1070\/RC2012v081n07ABEH004231","article-title":"Reactivity of 1,2-dithioles","volume":"81","author":"Ogurtsov","year":"2012","journal-title":"Russ. Chem. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1016\/S0040-4020(01)93760-3","article-title":"Studies on organophosphorus compounds. 28. Syntheses of 3H-1,2-dithiole-3-thiones and 4H-1,3,2-oxazaphosphorine derivatives from the dimer of para-methoxyphenylthionophosphine sulfide and derivatives of 3-oxo carboxylic-acids","volume":"35","author":"Pedersen","year":"1979","journal-title":"Tetrahedron"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"5829","DOI":"10.1016\/j.bmcl.2014.10.005","article-title":"Synthesis and structure\u2013activity relationships study of dithiolethiones as inducers of glutathione in the SH-SY5Y neuroblastoma cell line","volume":"24","author":"Brown","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"520","DOI":"10.1016\/j.ejmech.2016.06.055","article-title":"4,5-Diaryl-3H-1,2-dithiole-3-thiones and related compounds as combretastatin A-4\/oltipraz hybrids: Synthesis, molecular modelling and evaluation as antiproliferative agents and inhibitors of tubulin","volume":"122","author":"Wang","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2843","DOI":"10.1016\/j.bmc.2016.04.054","article-title":"Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor","volume":"24","author":"Lee","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6461","DOI":"10.1021\/jo0256742","article-title":"Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane","volume":"67","author":"Curphey","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2214","DOI":"10.1021\/acs.jafc.9b06360","article-title":"Synthesis of dithiolethiones and identification of potential neuroprotective agents via activation of Nrf2-driven antioxidant enzymes","volume":"68","author":"Song","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2137","DOI":"10.1016\/0040-4039(96)00209-2","article-title":"One-pot synthesis of 5-alkylthio-3H-1,2-dithiole-3-thiones","volume":"37","author":"Aimar","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1749","DOI":"10.1055\/s-2000-8202","article-title":"One-Pot Synthesis of 5-Alkylthio-3H-1,2-dithiole-3-thiones: Advantages and scope","volume":"2000","author":"Aimar","year":"2000","journal-title":"Synthesis"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1947","DOI":"10.1016\/S0040-4039(02)00180-6","article-title":"One-pot synthesis of 3H-1,2-dithiole-3-thione derivatives from dithiolmalonic esters","volume":"43","author":"Aimar","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6977","DOI":"10.1016\/S0040-4039(00)01191-6","article-title":"Dianions of 3-oxodithioic acids: Preparation and conversion to 3H-1,2-dithiole-3-thiones","volume":"41","author":"Curphey","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1682","DOI":"10.1080\/10426507.2014.887075","article-title":"Oxoketene dithiols: Synthesis of some heterocycles as antimicrobials utilizing shrimp chitin as a natural catalyst","volume":"189","author":"Zayed","year":"2014","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_38","first-page":"4509","article-title":"Dihydropyrimidines as precursors for synthesizing of oxoketene gem-dithiol and 1,2-dithiol-3-thione, a facile synthesis and convenient reaction transformations","volume":"63","author":"Hassan","year":"2020","journal-title":"Egypt. J. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"11594","DOI":"10.1021\/acs.joc.6b01802","article-title":"Switching selectivity of \u03b1-enolic dithioesters: One pot access to functionalized 1,2- and 1,3-dithioles","volume":"81","author":"Koley","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5809","DOI":"10.1016\/S0040-4039(02)01179-6","article-title":"Fluorinated ketene dithioacetals. Part 9: Synthesis and some chemical properties of new fluorinated 3H-1,2-dithiole-3-thiones","volume":"43","author":"Timoshenko","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1021\/cr60234a004","article-title":"The chemistry of 1,2-dithiole-3-thiones","volume":"65","author":"Landis","year":"1965","journal-title":"Chem. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1349","DOI":"10.1055\/s-0035-1560603","article-title":"Synthesis of amino-ADT provides access to hydrolytically stable amide-coupled hydrogen sulfide releasing drug targets","volume":"27","author":"Hammers","year":"2016","journal-title":"Synlett"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/j.ejmech.2019.04.046","article-title":"Appendix A. dithioloquinolinethiones as new potential multitargeted antibacterial and antifungal agents: Synthesis, biological evaluation and molecular docking studies","volume":"175","author":"Kartsev","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1577","DOI":"10.1039\/C4MD00180J","article-title":"Cytoprotective effects of hydrogen sulfidereleasing N-methyl-D-aspartate receptor antagonists mediated by intracellular sulfane sulfur","volume":"5","author":"Marutani","year":"2014","journal-title":"Med. Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"7671","DOI":"10.1016\/j.tetlet.2004.08.091","article-title":"A convenient route to 4-mercapto-1,2-dithiole-3-thiones from terminal alkynes","volume":"45","author":"Adams","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"5283","DOI":"10.1016\/j.tetlet.2014.07.104","article-title":"Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes","volume":"55","author":"Adams","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1016\/j.jorganchem.2004.01.022","article-title":"Formation of 5-phenyl-1,2-dithiole-3-thione from molybdenum dithiopropiolato complexes","volume":"689","author":"Mathur","year":"2004","journal-title":"J. Organomet. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3911","DOI":"10.1002\/adsc.201800846","article-title":"Copper-catalyzed defluorinative thioannulation of trifluoropropynes for the synthesis of 1,2-dithiole-3-thiones","volume":"360","author":"Wei","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7894","DOI":"10.1021\/acs.joc.9b00685","article-title":"Copper-catalyzed tandem sulfuration\/annulation of propargylamines with sulfur via C-N bond cleavage","volume":"84","author":"Xu","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1070\/RC2014v083n03ABEH004354","article-title":"Sulfur monochloride in organic syntheses","volume":"83","author":"Konstantinova","year":"2014","journal-title":"Russ. Chem. Rev."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/S0065-2725(07)00004-9","article-title":"Sulfur monochloride in the synthesis of heterocyclic compounds","volume":"96","author":"Konstantinova","year":"2008","journal-title":"Adv. Heterocycl. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.mencom.2009.03.001","article-title":"Design of sulfur heterocycles with sulfur monochloride: Retrosynthetic analysis and prospects","volume":"19","author":"Konstantinova","year":"2009","journal-title":"Mendeleev Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"837","DOI":"10.1007\/s10593-020-02740-2","article-title":"Synthesis of sulfur-containing heterocycles by electrophilic addition reactions of disulfur dichloride","volume":"56","author":"Rakitin","year":"2020","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1002\/anie.199702811","article-title":"From Hunig\u2019s base to bis[1,2]dithiolo[1,4]thiazines in one pot: The fast route to highly sulfurated heterocycles","volume":"36","author":"Marcos","year":"1997","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2189","DOI":"10.1021\/jo971864e","article-title":"Selective syntheses of bis[1,2]dithiolothiazines and bis[1,2]dithiolopyrroles from Hunig\u2019s base","volume":"63","author":"Rees","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5010","DOI":"10.1021\/jo9902345","article-title":"Synthesis of bis[1,2]dithiolo[1,4]thiazines and a [1,2]dithiolo[1,4]thiazine from tertiary diisopropylamines","volume":"64","author":"Rees","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3421","DOI":"10.1039\/b005068g","article-title":"Synthesis of N-unsubstituted bis[1,2]dithiolo[1,4]thiazines and bis[1,2]dithiolopyrroles","volume":"1","author":"Konstantinova","year":"2000","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Barriga, S., Garc\u00eda, N., Marcos, C.F., Neo, A.G., and Torroba, T. (2002). New chemistry of bis[1,2]dithiolo[1,4]thiazines and bis[1,2]dithiolopyrroles. ARKIVOC, 212\u2013223.","DOI":"10.3998\/ark.5550190.0003.619"},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Marcos, C.F., Polo, C., Rakitin, O.A., Rees, C.W., and Torroba, T. (1997). One-pot synthesis and chemistry of bis[1,2]dithiolopyrroles. J. Chem. Soc. Chem. Commun., 879\u2013880.","DOI":"10.1039\/a701340j"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2409","DOI":"10.1039\/b105243h","article-title":"Synthesis of bis[1,2]dithiolo[1,4]thiazine imines from Hunig\u2019s base","volume":"1","author":"Amelichev","year":"2001","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1070\/MC2001v011n05ABEH001493","article-title":"New reactions of Hunig\u2019s base with S2Cl2: Formation of monocyclic 1,2-dithioles","volume":"11","author":"Konstantinova","year":"2001","journal-title":"Mendeleev Commun."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1007\/s11172-006-0228-9","article-title":"Synthesis of 5-mercapto-1,2-dithiole-3-thiones and their transformation into 5-chloro-1,2-dithiol-3-ones","volume":"55","author":"Konstantinova","year":"2006","journal-title":"Russ. Chem. Bull."},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Marcos, C.F., Rakitin, O.A., Rees, C.W., Souvorova, L.I., Torroba, T., White, A.J.P., and Williams, D.J. (1998). Tertiary amine\u2014S2Cl2 chemistry: Interception of reaction intermediates. J. Chem. Soc. Chem. Commun., 453\u2013454.","DOI":"10.1039\/a708396c"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1021\/ol034145x","article-title":"Synthesis, chemistry, and dynamic NMR study of new atropisomeric 4-dialkylamino-5-chloro-1,2-dithiole-3-thiones","volume":"5","author":"Pascual","year":"2003","journal-title":"Org. Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1007\/s11172-014-0469-y","article-title":"Synthesis of 4,8-dihydro-7H-[1,2]dithiolo[3,4-b][1,2,5]oxadiazolo-[3,4-e] pyrazine-7-thione as a new heterocyclic system","volume":"63","author":"Konstantinova","year":"2014","journal-title":"Russ. Chem. Bull."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"4376","DOI":"10.1021\/jo9825005","article-title":"Synthesis of sulfur rich 1,2- and 1,3-dithiolodisulfides and thiodesaurines from diisopropyl sulfide","volume":"64","author":"Rees","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1070\/MC2004v014n03ABEH001912","article-title":"Regioselective synthesis of pentathiepino-fused pyrroles and indoles","volume":"14","author":"Konstantinova","year":"2004","journal-title":"Mendeleev Commun."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2178","DOI":"10.1016\/j.tet.2009.01.069","article-title":"A one-pot synthesis and 1,3-dipolar cycloaddition of [1,2]dithiolo[4,3-b]indole-3(4H)-thiones","volume":"65","author":"Konstantinova","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1055\/s-0037-1611692","article-title":"Exploration and development of a C-H activated route to access the [1,2]dithiolo[4,3-b]indole-3(4H)-thione core and related derivatives","volume":"30","author":"Asquith","year":"2019","journal-title":"Synlett"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4621","DOI":"10.1021\/om9003972","article-title":"An unexpected sequence: From phosphole sulfide to phosphole- and thiophene-annulated 1,2-dithiole-3-thiones","volume":"28","author":"Ciric","year":"2009","journal-title":"Orgametallics"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"5725","DOI":"10.1021\/ol052557v","article-title":"Abnormally mild synthesis of bis(dithiolo)pyrroles from 2,5-dimethylpyrroles","volume":"7","author":"Amelichev","year":"2005","journal-title":"Org. Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"5555","DOI":"10.1021\/acs.orglett.0c01914","article-title":"Selective [3 + 2] cycloaddition of cyclopropenone derivatives and elemental chalcogens","volume":"22","author":"Wu","year":"2020","journal-title":"Org. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"2341","DOI":"10.1080\/10426507.2011.600743","article-title":"A facile synthesis of 3H-benzo[1,2]dithiole-3-thiones and their condensation with active methylene compounds","volume":"186","author":"Jin","year":"2011","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"802","DOI":"10.1055\/s-1977-24588","article-title":"Eine einfache und ergiebige Herstellung von 3-Thioxo-1,2-dithiol (1,2-Trithion)","volume":"1977","author":"Meinetsberger","year":"1977","journal-title":"Synthesis"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1754","DOI":"10.1007\/s11176-005-0095-3","article-title":"New ways of synthesis of 1,2-dithiole-3-thione","volume":"74","author":"Korchevin","year":"2004","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"8861","DOI":"10.1016\/S0040-4039(96)02063-1","article-title":"Polyacetyl-substituted tetrathiafulvalenes and 1,3-dithiolic derivatives from hex-3-yn-2,5-dione","volume":"37","author":"Leriche","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2205","DOI":"10.1080\/10426500701407730","article-title":"Thiafulvenes and thiafulvalenes in organic chemistry: Synthesis and study its behavior towards some chemical reagents","volume":"182","author":"Zayed","year":"2007","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1070\/MC2003v013n02ABEH001750","article-title":"4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles","volume":"13","author":"Ogurtsov","year":"2003","journal-title":"Mendeleev Commun."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1021\/jo501473z","article-title":"Structural conformers of (1,3-dithiol-2-ylidene)ethanethioamides: The balance between thioamide rotation and preservation of classical sulfur-sulfur hypervalent bonds","volume":"80","author":"Fuertes","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1021\/ol0476669","article-title":"Synthesis of thienopyrantiones by a new molecular rearrangement","volume":"7","author":"Ogurtsov","year":"2005","journal-title":"Org. Lett."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"2243","DOI":"10.3987\/COM-06-10849","article-title":"Novel formation of 1,2-dithiolane-3-thione from beta-dithiolactone","volume":"68","author":"Shigetomi","year":"2006","journal-title":"Hetetocycles"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1007\/BF02324643","article-title":"4,4-Dimethyl-4,5-dihydro-1,2-dithiolo-[3,4-c]quinoline-1-thiones in 1,3-dipolar cycloaddition reactions with acetylenic dipolarophiles","volume":"35","author":"Shikhaliev","year":"1999","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_83","first-page":"450","article-title":"New heterocyclic compounds derived from 8-R-4,4-dimethyl-2,3-dithiolo-[5,4-c]quinoline-1-thiones","volume":"70","author":"Shikhaliev","year":"2000","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"534","DOI":"10.1007\/s10593-006-0122-2","article-title":"Novel heterocyclic systems on the basis of 8-R-4,5-dihydro-4,4-dimethyl-2,3-dithiolo[3,4-c]-quinoline-1-thiones","volume":"42","author":"Medvedeva","year":"2006","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"6439","DOI":"10.1021\/jo020015a","article-title":"Synthesis of [1,3]dithiole and spiro[1,3]dithiole thiopyran derivatives of the [1,2]dithiolo[1,4]thiazine ring system","volume":"67","author":"Barriga","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"3672","DOI":"10.1021\/jo035748p","article-title":"Synthesis of highly branched sulfur-nitrogen heterocycles by cascade cycloadditions of [1,2]dithiclo[1,4]thiazines and [1,2]dithiolopyrroles","volume":"69","author":"Barriga","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"918","DOI":"10.1023\/A:1020913328392","article-title":"1,3-Dipolar cycloaddition of ethyl propiolate to 4,5-dihydro-4,4-dimethyl-1,2-dithiolo[5,4-c]quinoline-1 thiones","volume":"38","author":"Medvedeva","year":"2002","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1692","DOI":"10.1002\/asia.201000063","article-title":"A selective chromogenic probe for mercury(ii) and cyanide in aqueous buffered solution from a cycloaddition reaction of an ynamine to polycyclic dithiolethiones","volume":"5","author":"Fuertes","year":"2010","journal-title":"Chem. Asian J."},{"key":"ref_89","doi-asserted-by":"crossref","unstructured":"Granados, A.M., Fracaroli, A.M., de Rossi, R.H., Fuertes, P., and Torroba, T. (2008). Alkynyl Fischer carbene complex as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene: Synthesis of E-dithiafulvene thione and dithioesters. Chem. Commun., 483\u2013485.","DOI":"10.1039\/B715857B"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"2213","DOI":"10.1021\/jo500076c","article-title":"Synthesis of pyrrolidine-fused 1,3-dithiolane oligomers by the cycloaddition of polycyclic dithiolethiones to maleimides and evaluation as mercury(ii) indicators","volume":"79","author":"Fuertes","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1080\/00304949309457947","article-title":"The use of isocyanides in heterocyclic synthesis\u2014A review","volume":"25","author":"Marcaccini","year":"1993","journal-title":"Org. Prep. Proc. Int."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"5766","DOI":"10.1021\/jo010368u","article-title":"Synthesis of thiadiazole, dithietane, and imine derivatives of the [1,2]dithiolo[1,4]thiazine ring system","volume":"66","author":"Barriga","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"430","DOI":"10.1007\/s11172-010-0028-0","article-title":"Synthesis and thermal stability of imino-1,3-dithietanes. Influence of structural factors","volume":"58","author":"Ogurtsov","year":"2009","journal-title":"Russ. Chem. Bull."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1070\/MC2005v015n02ABEH002086","article-title":"Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones","volume":"15","author":"Ogurtsov","year":"2005","journal-title":"Mendeleev Commun."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1790","DOI":"10.1007\/s11172-008-0240-3","article-title":"A novel transformation of 1,2-dithiole-3-thiones into 1,3-thiazine-4-thiones","volume":"57","author":"Ogurtsov","year":"2008","journal-title":"Russ. Chem. Bull."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"4149","DOI":"10.1002\/ejoc.201900142","article-title":"Synthesis of 6,7-dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-dithiolo-3-(thi)ones","volume":"2019","author":"Ogurtsov","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1007\/s11172-012-0070-1","article-title":"Thiete-2-thiones in the synthesis of 1,3-thiazine-4-thiones from 1,2-dithiole-3-thiones","volume":"61","author":"Ogurtsov","year":"2012","journal-title":"Russ. Chem. Bull."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1016\/j.jfluchem.2006.02.013","article-title":"Reduction of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione with sodium sulfide: Synthesis of fluoro-containing sulfur-rich heterocycles","volume":"127","author":"Fesun","year":"2016","journal-title":"J. Fluorine Chem."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"808","DOI":"10.1021\/jo052168e","article-title":"Synthesis of 1,3-dithiin dithioortho esters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones","volume":"71","author":"Granados","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"8037","DOI":"10.1016\/S0040-4039(02)01971-8","article-title":"Insertion of Fischer carbene complexes into the carbon-carbon bond. Ring expansion of a sulfur heterocycle from five- to six-membered","volume":"43","author":"Granados","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1002\/jhet.5570420114","article-title":"An approach to biologically important s-heterocycles, dithiocarbamyls, and their relevant phosphono derivatives","volume":"42","author":"Khidre","year":"2005","journal-title":"J. Heterocycl. Chem."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1080\/17415993.2010.499942","article-title":"Ring opening\u2013ring closure of 4-phenyl-1,2-dithiole-3-thione: Convenient route to novel thiinethione derivatives by the reaction with active methylene nitriles","volume":"31","author":"Barsy","year":"2010","journal-title":"J. Sulfur Chem."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/10426500008076320","article-title":"Ring-opening ringn-closure of 4-phenyl-1,2-dithiole-3-thione. novel synthesis of thio-pyrano[2,3-b]pyrane derivatives","volume":"165","author":"Barsy","year":"2000","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"2255","DOI":"10.1080\/713744568","article-title":"Ring opening-ring closure of 4-phenyl-1,2-dithiole-3-thione: Reaction with \u03b1, \u03b2-unsaturated nitriles","volume":"178","author":"Barsy","year":"2003","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1021\/jm991044p","article-title":"Synthesis and in vitro anti-Mycobacterium activity of N-alkyl-1,2-dihydro-2-thioxo-3-pyridinecarbothioamides. Preliminary toxicity and pharmacokinetic evaluation","volume":"43","author":"Pagani","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1016\/S0014-827X(00)00084-7","article-title":"3H-[1,2]Dithiolo[3,4-b]pyridine-3-thione and its derivatives\u2014Synthesis and antimicrobial activity","volume":"55","author":"Pregnolato","year":"2000","journal-title":"Farmaco"},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1016\/0040-4039(96)00941-0","article-title":"The formation of 1,2-propadiene-1,3-dithione (carbon subsulfide) from flash vacuum pyrolysis of 1,2-dithiole-3-thiones","volume":"37","author":"Pedersen","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1002\/jhet.5570360341","article-title":"Synthesis and X-ray structure of a novel 1,2,4-trithiolane","volume":"36","author":"Bryce","year":"1999","journal-title":"J. Heterocycl. Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"1692","DOI":"10.5012\/bkcs.2004.25.11.1692","article-title":"Sulfurization of trivalent phosphorus compounds with 1,2-dithiole-3-thione","volume":"25","author":"Drabowicz","year":"2004","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_110","doi-asserted-by":"crossref","unstructured":"Fracaroli, A.M., Kreiker, J., de Rossi, R.H., and Granados, A.M. (2007). Synthesis of 5-(alkylthio or arylthio)-3H-1,2-dithiol-3-one derivatives. ARKIVOC, 279\u2013284.","DOI":"10.3998\/ark.5550190.0008.424"},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1134\/S1070428006010192","article-title":"Chlorination and oxidation of 4-fluoro-5-tetrafluoroethyl-1,2-dithiole-3-thione","volume":"42","author":"Fesun","year":"2006","journal-title":"Russ. J. Org. Chem."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"946","DOI":"10.1071\/CH09517","article-title":"Synthesis and preliminary pharmacological evaluation of aryl dithiolethiones with cyclooxygenase-2-selective inhibitory activity and hydrogen sulfide-releasing properties","volume":"63","author":"Zanatta","year":"2010","journal-title":"Aust. J. Chem."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"1721","DOI":"10.1080\/10426500307824","article-title":"Synthesis of 5-formyl and 5-acyl-1,2-dithiole-3-ones","volume":"178","author":"Gargadennec","year":"2003","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.jorganchem.2008.10.002","article-title":"Substituent effects of 1,2-dithiole groups on the electrochemical oxidation of some ferrocenyl-1,2-dithiole compounds","volume":"694","author":"Abasq","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"2307","DOI":"10.1080\/10426500600616860","article-title":"The 3-thioxo-1,2-dithiol-4-yl group: A versatile one endowed also with a -R electronic effect","volume":"181","author":"Krugler","year":"2006","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"3690","DOI":"10.1021\/jo991884b","article-title":"A facile and convenient synthesis of 3-alkylamino-5-arylthiophenes with a variety of substituents at C-2 and studies of reaction mechanisms","volume":"65","author":"Kim","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_117","first-page":"624","article-title":"N2S2 Tetradentate ligands for soft cationic species\u2014preparation of new ligands of potential interest in nuclear-medicine","volume":"132","author":"Guemas","year":"1995","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"1243","DOI":"10.1135\/cccc20031243","article-title":"Syntheses and structure study on 3,3a lambda(4),4-trithia-1-azapentalenes and their 3-oxa analogues","volume":"68","author":"Marek","year":"2003","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_119","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1135\/cccc20060650","article-title":"Transformation of 1,2-dithiole-3-thiones into 1,6,6a lambda(4)-trithiapentalenes via reaction with bromoethanones","volume":"71","author":"Pazdera","year":"2006","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1002\/jhet.5570400121","article-title":"Structural aspects of 5-methylthio-1-oxa-6,6a lambda(IV)-dithia-2-azapentalenes","volume":"40","author":"Finner","year":"2003","journal-title":"J. Heterocycl. Chem."},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1134\/S1070428002120187","article-title":"Synthesis of 3-imino and 3-ylideno derivatives of 4-fluoro-5-polyfluoroalkyl-1,2-dithiolenes","volume":"42","author":"Fesun","year":"2006","journal-title":"Russ. J. Org. Chem."},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1016\/S0223-5234(97)89857-1","article-title":"Antimicrobial activity of N-hydroxyalkyl 1,2-benzisothiazol-3(2H)-ones and their thiono analogues","volume":"31","author":"Borgna","year":"1996","journal-title":"Eur. J. Med. Chem."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"847","DOI":"10.1002\/jhet.5570320328","article-title":"Synthesis of 3H-thieno[3,2-c]-1,2-dithiole-3-thione and its reaction with n-butylamine","volume":"32","author":"Pregnolato","year":"1995","journal-title":"J. Heterocycl. Chem."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1007\/s11030-013-9499-x","article-title":"A serendipitous one-step conversion of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: An experimental and theoretical study","volume":"18","author":"Couto","year":"2014","journal-title":"Mol. Divers."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"1076","DOI":"10.1007\/s11172-013-0144-8","article-title":"Synthesis of 1-[(1,2-dithiol-3-ylidene)methyl]pyrrolo[1,2-a]pyrazines and 2-[(1,2-dithiol-3-ylidene)methyl]pyridines from 1,2-dithiole-3-thiones","volume":"62","author":"Ogurtsov","year":"2013","journal-title":"Russ. Chem. Bull."},{"key":"ref_126","first-page":"50","article-title":"Reactions of trialkyl phosphites with 5-p-chlorophenyl-4-cyano-1,2-dithiole-3-thione and with 5-phenyl-1,2,4-dithiazol-3-one and its thione derivative","volume":"26","author":"Abdou","year":"1995","journal-title":"J. Chem. Res. S"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"3421","DOI":"10.1016\/S0040-4020(01)81633-1","article-title":"Reactivity of substituted 1,2-dithiole-3-thiones with sodium ethanethiolate\u2014a convenient route to a novel heterocycle","volume":"43","author":"Largeron","year":"1987","journal-title":"Tetrahedron"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3595\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:13:31Z","timestamp":1760163211000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3595"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,6,11]]},"references-count":127,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2021,6]]}},"alternative-id":["molecules26123595"],"URL":"https:\/\/doi.org\/10.3390\/molecules26123595","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,6,11]]}}}