- Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N -Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions
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A highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of subst
- Lu, Yuhan,Sun, Yadong,Abdukader, Ablimit,Liu, Chenjiang
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supporting information
p. 1044 - 1048
(2021/05/05)
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- Synthesis method of 1, 2, 3-thiadiazole derivative
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The invention belongs to the technical field of compound preparation, and discloses a synthesis method of a 1, 2, 3-thiadiazole derivative. The synthesis method of the 1, 2, 3-thiadiazole derivative comprises the following steps: taking an N-tosylhydrazon
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Paragraph 0109-0140
(2021/08/28)
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- Selective transformations of 2-(p-toluenesulfonyl)-N-tosylhydrazones to substituted 1,2,3-thiadiazoles
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Selective transformations of 2-(p-toluenesulfonyl)-N-tosylhydrazones with different sulfur sources have been established. A series of 4-aryl-1,2,3-thiadiazoles and novel 4-aryl-5-tosyl-1,2,3-thiadiazoles were selectively constructed by the adjustment of reaction conditions. These protocols feature short reaction time, good compatibility of functional group, easily available materials, and good selectivity.
- Feng, Yijiao,He, Jing,Li, Weiwei,Yang, Zhen,Wei, Yueting,Liu, Ping,Zhao, Jixing,Gu, Chengzhi,Wang, Wenli
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supporting information
(2020/12/09)
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- I2/CuCl2-promoted one-pot three-component synthesis of aliphatic or aromatic substituted 1,2,3-thiadiazoles
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An efficient I2/CuCl2-promoted one-pot three-component strategy for the construction of 1,2,3-thiadiazoles from aliphatic- or aromatic-substituted methyl ketones, p-toluenesulfonyl hydrazide, and potassium thiocyanate has been develo
- Wang, Can,Geng, Xiao,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Cui, Yan-Fang,Wu, An-Xin
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supporting information
p. 8134 - 8137
(2019/07/15)
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- Preparation method of thiadiazole containing aryl group and alkyl group
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The invention discloses a preparation method of thiadiazole containing an aryl group and an alkyl group. Methyl ketone, p-toluenesulfonhydrazide and potassium thiocyanate which are used as a substrateundergo a three-component one-pot reaction in DMSO used
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Paragraph 0020-0024
(2019/08/30)
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- Metal- and Oxidant-free Electrosynthesis of 1,2,3-Thiadiazoles from Element Sulfur and N-tosyl Hydrazones
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A metal- and oxidant-free electrochemical method for synthesizing 1,2,3-thiadiazoles by inserting element sulfur into N-tosyl hydrazones is reported. This electrochemical transformation engages electrons as reagents to achieve redox processes, and avoid e
- Mo, Shi-Kun,Teng, Qing-Hu,Pan, Ying-Ming,Tang, Hai-Tao
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supporting information
p. 1756 - 1760
(2019/02/24)
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- Perylenequinonoid-Catalyzed [4 + 1] and [4 + 2] Annulations of Azoalkenes: Photocatalytic Access to 1,2,3-Thiadiazole/1,4,5,6-Tetrahydropyridazine Derivatives
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Nitrogen-containing heterocycles are especially considered "privileged" structural scaffolds for the development of new drugs. However, traditional methods of organic synthesis are mainly based on thermal cycloaddition reaction; thus, the exploration of n
- Zhang, Yan,Cao, Yuan,Lu, Liushen,Zhang, Shiwei,Bao, Wenhao,Huang, Shuping,Rao, Yijian
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supporting information
p. 7711 - 7721
(2019/06/17)
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- Cascade Trisulfur Radical Anion (S3?-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles
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Trisulfur radical anion (S3?-) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3?- is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C-S and N-S bonds via S3?- addition and electron detosylation under mild conditions.
- Liu, Bei-Bei,Bai, Hui-Wen,Liu, Huan,Wang, Shun-Yi,Ji, Shun-Jun
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p. 10281 - 10288
(2018/07/25)
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- Stereochemistry and mechanistic insights in the [2t + 2i + 2i] annulations of thioketenes and imines
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Stereochemical models and mechanistic insights are proposed for [2t + 2i + 2i] annulations of thioketenes and imines on the basis of experimental and computational investigations. In the [2t + 2i + 2
- He, Wei,Zhuang, Junpeng,Du, Hongguang,Yang, Zhanhui,Xu, Jiaxi
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p. 9424 - 9432
(2017/11/22)
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- Coupled Flavin-Iodine Redox Organocatalysts: Aerobic Oxidative Transformation from N-Tosylhydrazones to 1,2,3-Thiadiazoles
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A bioinspired two-component redox organocatalyst system using 1,10-bridged flavinium and NH4I was developed to perform environmentally friendly aerobic oxidative ring formation of 1,2,3-thiadiazoles from N-tosylhydrazones and sulfur. The redox
- Ishikawa, Tatsuro,Kimura, Maasa,Kumoi, Takuma,Iida, Hiroki
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p. 4986 - 4989
(2017/08/17)
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- TBAI-Catalyzed Reaction between N-Tosylhydrazones and Sulfur: A Procedure toward 1,2,3-Thiadiazole
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A TBAI-catalyzed reaction between N-tosyl hydrazone and sulfur was developed, leading to 1,2,3-thiadiazoles in moderate to good yields. It represents a facile and practical procedure to access thiadiazole under metal-free conditions. This procedure serves
- Chen, Jiangfei,Jiang, Yan,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 271 - 275
(2016/01/15)
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- Ionic liquid as soluble support for synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles
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A convenient synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles was achieved using an ionic liquid as a novel soluble support. Ionic liquid-supported sulfonyl hydrazine was synthesized and reacted with a number of ketones to afford the corresponding ionic liquid-supported hydrazones that were converted to 1,2,3-thiadiazoles in the presence of thionyl chloride. The reaction of ionic liquid-supported hydrazones with selenium dioxide in acetonitrile afforded 1,2,3-selenadiazoles. The advantages of this methodology were the ease of workup, simple reaction conditions, and high purity.
- Kumar, Anil,Muthyala, Manoj Kumar,Choudhary, Sunita,Tiwari, Rakesh K.,Parang, Keykavous
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p. 9391 - 9396,6
(2012/12/11)
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- Formation of reagent-selective products from 2-(4,5-dihydrothi- azol-2-ylthio)-1-arylethanone with different nucleophiles
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The reactions of 2-(4,5-dihydrothiazol-2-ylthio)-1-arylethanone with different nucleophiles including semicarbazide hydrochloride, hydroxylamine hydrochloride, hydrazine, ethylenediamine and aminoethanol have been investigated, and the formation of a variety of products with different reagents is highlighted.
- Saravanan,Mohan,Muthusubramanian
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experimental part
p. 71 - 84
(2011/12/05)
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- Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives)
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A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N-H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56-50 μM.
- Hayat, Faisal,Salahuddin, Attar,Zargan, Jamil,Azam, Amir
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experimental part
p. 6127 - 6134
(2011/01/13)
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- Traceless solid-phase synthesis of 1,2,3-thiadiazole derivatives from resin-bound acylhydrazine
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A novel synthesis of 1,2,3-thiadiazole derivatives using a traceless solid-phase approach is described, in which many kinds of 1,2,3-thiadiazole derivatives were efficiently obtained in good yields and high purities via traceless cyclization cleavage of resin-bound acylhydrazones with thionyl chloride. Copyright Taylor & Francis Group, LLC.
- Liu, Zhanxiang,Mu, Yuanyuan,Lin, Jie,Chen, Yiya
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experimental part
p. 4407 - 4414
(2009/04/11)
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- Synthesis of lithium 1-alkynesulfenates by the mild oxidation of thiolates with a pinacolone-derived N-sulfonyloxaziridine
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Lithium 1-alkynethiolates, generated by a base-induced ring cleavage of 4-substituted 1,2,3-thiadiazoles, were efficiently converted into the corresponding sulfenate salts by mild oxidation using an N-sulfonyloxaziridine derived from pinacolone. In situ S
- Sandrinelli, Franck,Boudou, Cédric,Caupène, Caroline,Averbuch-Pouchot, Marie-Thérèse,Perrio, Stéphane,Metzner, Patrick
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p. 3289 - 3293
(2008/09/18)
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- 1,2,3-thiadiazole compounds, compositions and method of anti-thrombotic treatment
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Novel 1,2,3-thiadiazole compounds, new and old 1,2,3-thiadiazole compositions and method of anti-thrombotic treatment are systemically administered to a human or animal.
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- Electrosynthesis of (E)-Ethenyl-O-ethyl-thiocarbonates
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Electrochemical reductions of 4-aryl- and 4,5-diaryl-1,2,3-thiadiazols (1-5) in acetonitrile/0,1 M tetraalkylammonium-supporting-electrolyte at Hg-cathodes in the presence of ethylchloroformiate (CAE) yield (E)-S-(2-aryl) ethenyl- and S-(1,2-diaryl)etheny
- Hess, U.,Schulze, M.
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p. 901 - 908
(2007/10/02)
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- Synthesis of 1,2,3-Thiadiazole-5-carbaldehydes and their Conversion into 6aλ4-Thia-1,2,5,6-tetraazapentalenes
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A convenient method for the synthesis of the virtually unknown 1,2,3-thiadiazole-5-carbaldehydes consists in monobromination of the 5-methyl derivatives, followed by treatment with sodium azide and decomposition in concentrated sulfuric acid (6 -> 7 -> 9
- L'abbe, Gerrit,Frederix, Ann
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p. 1415 - 1418
(2007/10/02)
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- Synthesis and platelet aggregation inhibitory activity of 4,5-bis(substituted)-1,2,3-thiadiazoles
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Routine screening of compounds for inhibition of collagen-induced platelet aggregation in vitro revealed 4,5-bis-(4-methoxyphenyl)-1,2,3-thiadiazole was active and it represents the first example of a 1,2,3-thiadiazole with possible antithrombotic activit
- Thomas,Nishizawa,Zimmermann,Williams
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p. 442 - 446
(2007/10/02)
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- NOVEL RING CONTRACTIONS OF 2,7-DIHYDRO-3,6-DIPHENYL-1,4,5-THIADIAZEPINE VIA A HALOGENATION-DEHALOGENATION PROCESS
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2,7-Dihydro-3,6-diphenyl-1,4,5-thiadiazepine undergoes novel ring contractions via a halogenation-dehalogenation process in methanol, giving sulfur-containing five-membered cyclic compounds: this result is a great contrast to the ring contraction with ext
- Kamata, Kichinosuke,Tsuge, Otohiko
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p. 1497 - 1500
(2007/10/02)
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- Kinetics and Mechanism of the Reaction of Thionyl Chloride with Substituted Acetophenone Semicarbazones. The Synthesis of 1,2,3-Thiadiazoles
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The reaction of thionyl chloride with a series of para-substituted acetophenone semicarbazones, which gives 1,2,3-thiadiazoles, involved an electrophilic attack.The rates correlated with the substituent ?+ constants and gave a Hammett ρ value o
- Butler, Richard N.,O'Donoghue, Denis A.
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p. 1223 - 1228
(2007/10/02)
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- Unsaturated Compounds containing Nitrogen. Part 4. Further Reactions of 1-Chloro-2,3-diazabutadienes with S-Nucleophiles
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1-Chloro-1,4-diaryl-2,3-diazabutadienes (Ar1CCl=NN=CHAr2), prepared by the reaction of thionyl chloride with aroylhydrazones (Ar1CONHN=CHAr2), react with thiosemicarbazide or thiocarbohydrazide to give 2-arylidenehydrazino-5-aryl-1,3,4-thiadiazoles, and with potassium thiocyanate to give 1-thiocyanato-1,4-diaryl-2,3-diazabutadienes which isomerize thermally to arylideneamino-5-aryl-1,3,4-thiadiazoles. 1-Chloro-1,4-diphenyl-2,3-diazabutadiene reacts with potassium ethylxanthate to give a 1-ethylxanthyl-2,3-diazabutadiene which on pyrolysis yields 2,5-diphenyl-1,3,4-thiadiazole.
- Flowers, William T.,Robinson, John F.,Taylor, David R.,Tipping, Anthony E.
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p. 349 - 355
(2007/10/02)
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- Reaction of Substituted Hydrazones with Thionyl Chloride and Sulfuryl Chloride
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Treatment of acetylhydrazones 2, ethoxycarbonylhydrazones 3, p-tolylsulfonylhydrazones 4 or semicarbazones 5 with thionyl chloride leads to the 1,2,3-thiadiazoles 6a-o.Sulfuryl chloride on the other hand accomplishes the transfer of chlorine without incorporating a sulfur atom.The new synthesized 1,2,3-thiadiazoles 6g-o are characterized in detail by spectroscopic methods.
- Meier, Herbert,Trickes, Georg,Laping, Elisabeth,Merkle, Ursula
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p. 183 - 192
(2007/10/02)
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- Methylation of 4-Phenyl-1,2,3-thiadiazole. Reaction of Nucleophiles with N-Methyl-1,2,3-thiadiazolium Salts and the Crystal Structure of the Products
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The methylation of 4-phenyl-1,2,3-thiadiazole yields both N-methylated products.These react differently with nucleophiles.The structure of the product of the reaction with morpholine has been determined through X-ray diffraction analysis.
- Auricchio, S.,Brueckner, S.,Giunchi, L. Malpezzi,Kozinsky, V. A.,Zelenskaja, O. V.
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p. 1217 - 1219
(2007/10/02)
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