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Sulfur reports Volume 21, 1998 - Issue 2
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Original Articles

Synthesis and Reactions of 1,2,3-Dithiazoles

Kyongtae Kim Department of Chemistry, Seoul National University, Seoul, 151-742, Korea
Pages 147-207 | Received 03 Mar 1998, Published online: 04 Oct 2006

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Vladimir Yarovenko, Igor Shedishev, Aleksandr Dudnik, Igor Zavarin & Michail Kraushkin. (2010) Synthesis and Reactivity of 2-(1,2,3-Dithiazol-5- Ylidene)Aminothiophenes. Phosphorus, Sulfur, and Silicon and the Related Elements 185:7, pages 1558-1570.
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Maria de Fatima Pereira, Valerie Thiery & Thierry Besson. (2006) Synthesis of novel 2,3-condensed thieno[2,3- ]pyrimidin-4-ones via Appel's salt chemistry. Journal of Sulfur Chemistry 27:1, pages 49-55.
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Alexandra Testard, Laurent Picot, Olivier Lozach, Melina Blairvacq, Laurent Meijer, Laurence Murillo, Jean-Marie Piot, Valérie Thiéry & Thierry Besson. (2005) Synthesis and evaluation of the antiproliferative activity of novel thiazoloquinazolinone kinases inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 20:6, pages 557-568.
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Articles from other publishers (45)

Andreas S. Kalogirou, Hans J. Oh & Christopher R. M. Asquith. (2023) The Synthesis and Biological Applications of the 1,2,3-Dithiazole Scaffold. Molecules 28:7, pages 3193.
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Konstantinos Plakas, Andreas S. Kalogirou, Andreas Kourtellaris & Panayiotis A. Koutentis. (2022) Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with 2-(Phenylsulfonyl)acetonitrile. Molbank 2022:1, pages M1322.
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Christos P. Constantinides, Maria Koyioni, Fadwat Bazzi, Maria Manoli, Daniel B. Lawson & Panayiotis A. Koutentis. (2021) Crystal Structure and Solid-State Packing of 4-Chloro-5H-1,2,3-dithiazol-5-one and 4-Chloro-5H-1,2,3-dithiazole-5-thione. Molecules 26:19, pages 5875.
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Kaitlyn A. Maffuid, Maria Koyioni, Chad D. Torrice, William A. Murphy, Heemaja K. Mewada, Panayiotis A. Koutentis, Daniel J. Crona & Christopher R.M. Asquith. (2021) Design and evaluation of 1,2,3-dithiazoles and fused 1,2,4-dithiazines as anti-cancer agents. Bioorganic & Medicinal Chemistry Letters 43, pages 128078.
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Ilia V. Baranovsky, Lidia S. Konstantinova, Mikhail A. Tolmachev, Vadim V. Popov, Konstantin A. Lyssenko & Oleg A. Rakitin. (2020) Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol-4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol-5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups. Molecules 25:17, pages 3768.
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Tuomo Laitinen, Ilia V. Baranovsky, Lidia S. Konstantinova, Antti Poso, Oleg A. Rakitin & Christopher R. M. Asquith. (2020) Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles. Antibiotics 9:7, pages 369.
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Boris Letribot, Régis Delatouche, Hervé Rouillard, Antoine Bonnet, Jean-René Chérouvrier, Lisianne Domon, Thierry Besson & Valérie Thiéry. (2018) Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones. Molecules 23:6, pages 1390.
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Lidia S. Konstantinova, Ilia V. Baranovsky, Elena A. Pritchina, Maksim S. Mikhailov, Irina Yu. Bagryanskaya, Nikolay A. Semenov, Irina G. Irtegova, Georgy E. Salnikov, Konstantin A. Lyssenko, Nina P. Gritsan, Andrey V. Zibarev & Oleg A. Rakitin. (2017) Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange. Chemistry - A European Journal 23:67, pages 17037-17047.
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Christopher R. M. Asquith, Lidia S. Konstantinova, Tuomo Laitinen, Marina L. Meli, Antti Poso, Oleg A. Rakitin, Regina Hofmann-Lehmann & Stephen T. Hilton. (2016) Evaluation of Substituted 1,2,3-Dithiazoles as Inhibitors of the Feline Immunodeficiency Virus (FIV) Nucleocapsid Protein via a Proposed Zinc Ejection Mechanism. ChemMedChem 11:19, pages 2119-2126.
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Mohamed S. Bekheit, Abdelbasset A. Farahat & Bakr F. Abdel-Wahab. (2016) Synthetic routes to thiazoloquinazolines. Chemistry of Heterocyclic Compounds 52:10, pages 766-772.
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Lidia Konstantinova, Ilia Baranovsky, Irina Irtegova, Irina Bagryanskaya, Leonid Shundrin, Andrey Zibarev & Oleg Rakitin. (2016) Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties. Molecules 21:5, pages 596.
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Maria Koyioni, Maria Manoli & Panayiotis A. Koutentis. (2015) The Reaction of DABCO with 4-Chloro-5 H -1,2,3-dithiazoles: Synthesis and Chemistry of 4-[ N -(2-Chloroethyl)piperazin-1-yl]-5 H -1,2,3-dithiazoles . The Journal of Organic Chemistry 81:2, pages 615-631.
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Andreas Kalogirou & Panayiotis Koutentis. (2015) A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride. Molecules 20:8, pages 14576-14594.
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Andreas S. Kalogirou, Sophia S. Michaelidou, Andrew J.P. White & Panayiotis A. Koutentis. (2015) Transformation of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile into 4-aminopyrido[2,3-d]pyrimidines and 2-(pyrid-2-yl)guanidines. Tetrahedron 71:12, pages 1799-1807.
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David C. McCutcheon, William B. Porterfield & Jennifer A. Prescher. (2015) Rapid and scalable assembly of firefly luciferase substrates. Organic & Biomolecular Chemistry 13:7, pages 2117-2121.
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Andreas S. Kalogirou, Irene C. Christoforou, Heraklidia A. Ioannidou, Manolis J. Manos & Panayiotis A. Koutentis. (2014) Ring transformation of (4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitriles to 3-haloisothiazole-5-carbonitriles. RSC Adv. 4:15, pages 7735-7748.
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Styliana I. Mirallai, Manolis J. Manos & Panayiotis A. Koutentis. (2013) One-Step Conversion of 2-Amino- N ′-arylbenzamidines into 3-Aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles Using 4,5-Dichloro-1,2,3-dithiazolium Chloride . The Journal of Organic Chemistry 78:19, pages 9906-9913.
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Panayiotis A. Koutentis, Maria Koyioni & Sophia S. Michaelidou. (2013) The conversion of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines into azine fused thiazole-2-carbonitriles. Org. Biomol. Chem. 11:4, pages 621-629.
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Paul M. Lahti. 2011. 93 169 .
Irene C. Christoforou, Andreas S. Kalogirou & Panayiotis A. Koutentis. (2009) The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry. Tetrahedron 65:48, pages 9967-9972.
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Sophia S. Michaelidou & Panayiotis A. Koutentis. (2009) The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine. Tetrahedron 65:40, pages 8428-8433.
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Alicia Foucourt, Elizabeth Chosson & Thierry Besson. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Andreas S. Kalogirou & Panayiotis A. Koutentis. (2009) The degradation of 4,5-dichloro-1,2,3-dithiazolium chloride in wet solvents. Tetrahedron 65:34, pages 6859-6862.
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Andreas S. Kalogirou & Panayiotis A. Koutentis. (2009) The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with DMSO: an improved synthesis of 4-chloro-1,2,3-dithiazol-5H-one. Tetrahedron 65:34, pages 6855-6858.
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Lidia S. Konstantinova, Oleg I. Bol’shakov, Natalia V. Obruchnikova, Hélène Laborie, Annabelle Tanga, Valérie Sopéna, Isabelle Lanneluc, Laurent Picot, Sophie Sablé, Valérie Thiéry & Oleg A. Rakitin. (2009) One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity. Bioorganic & Medicinal Chemistry Letters 19:1, pages 136-141.
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Maria de Fatima Pereira, Valérie Thiéry & Thierry Besson. (2007) Microwave-assisted regioselective N-alkylation of cyclic amidines. Tetrahedron Letters 48:43, pages 7657-7659.
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Maria de Fatima Pereira, Valérie Thiéry & Thierry Besson. (2007) Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles. Tetrahedron 63:4, pages 847-854.
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Alexandra Testard, Cédric Logé, Benoît Léger, Jean-Michel Robert, Olivier Lozach, Mélina Blairvacq, Laurent Meijer, Valérie Thiéry & Thierry Besson. (2006) Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3. Bioorganic & Medicinal Chemistry Letters 16:13, pages 3419-3423.
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Anne Beauchard, Hadjila Chabane, Sourisak Sinbandhit, Pierre Guenot, Valérie Thiéry & Thierry Besson. (2006) Synthesis of original thiazoloindolo[3,2-c]quinoline and novel 8-N-substituted-11H-indolo[3,2-c]quinoline derivatives from benzotriazoles. Part I. Tetrahedron 62:8, pages 1895-1903.
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Sonia Macho, Daniel Miguel, Teresa Gómez, Teresa Rodríguez & Tomás Torroba. (2005) From Cyclopentanone Oximes to Bis[1,2,3]dithiazolo- s -indacenes, Cyclopenta[ c ][1,2]thiazine, Pentathiepino-, Tetrathiino-, and Thienocyclopenta[1,2,3]dithiazoles as a Rich Source of New Materials . The Journal of Organic Chemistry 70:23, pages 9314-9325.
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Moon-Kook Jeon, Dong-Su Kim, Hyun Ju La, Deok-Chan Ha & Young-Dae Gong. (2005) Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives. Tetrahedron Letters 46:44, pages 7477-7481.
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François-René Alexandre, Amaya Berecibar, Roger Wrigglesworth, Laurence Perreux, Jean Guillon, Jean-Michel Léger, Valérie Thiéry & Thierry Besson. (2005) Synthesis of novel 1,3,4-benzotriazepine derivatives from 4-oxo-3,1-benzoxazine and 3,1-benzothiazine-2-carbonitriles. Tetrahedron 61:34, pages 8288-8294.
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Vladimir N. Yarovenko, Andrey A. Esﾕkov, Pavel A. Kondrashev, Anatolii V. Ignatenko, Igor V. Zavarzin, Lidia G. Vorontsova, Igor P. Sedishev, Mikhail M. Krayushkin & Zoya A. Starikova. (2005) Synthesis and Reactivity of N-Vinyl-1,2,3-dithiazolimines. HETEROCYCLES 65:7, pages 1601.
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Maria de Fatima Pereira, François René Alexandre, Valérie Thiéry & Thierry Besson. (2004) A rapid and convenient synthesis of novel 1-imino-2,3-dihydro-1H-pyrazino[2,1,-b]quinazolin-5-ones. Tetrahedron Letters 45:15, pages 3097-3099.
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Vladimir N. Yarovenko, Andrey A. Es'kov, George V. Zatonsky, Igor V. Zavarzin, Mikhail M. Krayushkin, Boris B. Averkiev & Mikhail yu. Antipin. (2009) Synthesis of azomethylene derivatives of 4‐chloro‐5 H ‐1,2,3‐dithiazole . Journal of Heterocyclic Chemistry 41:1, pages 37-43.
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Leanne Beer, Jaclyn L. Brusso, A. Wallace Cordes, Robert C. Haddon, Mikhail E. Itkis, Kristin Kirschbaum, Douglas S. MacGregor, Richard T. Oakley, A. Alan Pinkerton & Robert W. Reed. (2002) Resonance-Stabilized 1,2,3-Dithiazolo-1,2,3-dithiazolyls as Neutral π-Radical Conductors. Journal of the American Chemical Society 124:32, pages 9498-9509.
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Moon-Kook Jeon & Kyongtae Kim. (2002) Synthesis of 3-(alkylamino and anilino)-4-benzyloxycarbonyl-1H-pyrrole-2,5-diones via 5-[(alkylamino and anilino)(cyano)]-2,2-dimethyl-1,3-dioxane-4,6-diones. Tetrahedron Letters 43:18, pages 3415-3418.
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Kyongtae Kim & Pramod K. Mohanta. (2002) New Synthetic Route to Tetracyclic Quinazolin-4(3H)-one Ring System. HETEROCYCLES 57:8, pages 1471.
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Leanne Beer, A. Wallace Cordes, Robert C. Haddon, Mikhail E. Itkis, Richard T. Oakley, Robert W. Reed & Craig M. Robertson. (2002) A π-stacked 1,2,3-dithiazolyl radical. Preparation and solid state characterization of (Cl 2 C 3 NS)(ClC 2 NS 2 ) . Chem. Commun.:17, pages 1872-1873.
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Leanne Beer, James F. Britten, A. Wallace Cordes, Owen P. Clements, Richard T. Oakley, Maren Pink & Robert W. Reed. (2001) Benzo[2,1- c :3,4- c ‘ ]bis(1,2,3-thiaselenazole) (BSe) and Its Charge Transfer Chemistry. Crystal and Electronic Structure of [BSe] 3 [ClO 4 ] 2 . Inorganic Chemistry 40:18, pages 4705-4709.
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Tosha M. Barclay, Leanne Beer, A. Wallace Cordes, Richard T. Oakley, Kathryn E. Preuss, Robert W. Reed & Nicholas J. Taylor. (2001) 5,5‘-Bridged Bis(1,2,3-dithiazoles):  Spin States and Charge-Transfer Chemistry. Inorganic Chemistry 40:12, pages 2709-2714.
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Moon-Kook Jeon & Kyongtae Kim. (1999) Synthesis of new5-alkylidene-4-chloro-5H-1,2,3-dithiazoles and their stereochemistry. Tetrahedron 55:32, pages 9651-9667.
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T. M. Barclay, L. Beer, A. W. Cordes, R. C. Haddon, M. I. Itkis, R. T. Oakley, K. E. Preuss & R. W. Reed. (1999) trans -4,4‘-Dichloro-1,1‘,2,2‘,3,3‘-tetrathiadiazafulvalene (DC-TAF) and Its 1:1 Radical Cation Salts [DC-TAF][X]:  Preparation and Solid-State Properties of BF 4 - , ClO 4 - , and FSO 3 - Derivatives . Journal of the American Chemical Society 121:28, pages 6657-6663.
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Kyongtae Kim. (2010) ChemInform Abstract: Synthesis and Reactions of 1,2,3‐Dithiazoles. ChemInform 30:10.
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Kyongtae Kim & Yong-Goo Chang. (1999) A Facile Synthesis of N-Arylcyanoformamidoximes, 4-Aryl-3-cyano-1,2,4-oxadiazin-5(6H)-ones, 2-Cyanoquinazoline-3-oxides, and 2-Cyanoquinazolines via 5-Arylimino-4-chloro-5H-1,2,3-dithiazoles. HETEROCYCLES 51:11, pages 2653.
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