- A copper-catalyzed approach for the synthesis of asymmetrical disubstituted 1,2,4-thiadiazoles via elemental sulfur-mediated decarboxylative redox cyclization
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The variety of asymmetrical disubstituted 1,2,4-thiadiazoles are smoothly prepared by copper-catalyzed approach, which employed arylacetic acids and amidines as substrates, and elemental sulfur to mediate decarboxylative redox cyclization. The advantages of this method are simple, efficient, and ligand-free. In addition, this method can provide products in moderate to good yields.
- Liu, Yafei,Zhang, Yurong,Zhang, Jun,Hu, Liang,Han, Shiqing
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Read Online
- Visible-light promoted serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles via oxidative dimerization of thiobenzamides
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In the present manuscript, we report serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles with the aid of a household compact fluorescent lamp (CFL). In presence of α-bromo-β-diketone, thiobenzamides undergo oxidative dimerization to generate corresponding 3,5-diaryl-1,2,4-thiadiazoles in excellent yields in just 5 min instead of expected 2-aryl-4-methyl-5-acylthiazoles. Inhibition of the reaction by free radical scavenger (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) indicates that the dimerization takes place through a free radical process. The synthetic value of the developed protocol was established by synthesizing over eleven diverse 1,2,4-thiadiazoles in a shorter duration with exceptionally high purity and simple work-up procedure under environment benign additive-free conditions.
- Aggarwal, Ranjana,Hooda, Mona
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- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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p. 3398 - 3402
(2021/06/25)
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- Highly efficient synthesis of 1,2,4-thiadiazoles from thioamides utilizing tetra(n-butyl)ammonium peroxydisulfate
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A new synthetic approach to 1,2,4-thiadiazoles using tetra(n-butyl)ammonium peroxydisulfate via oxidative dimerization of thioamides is described. This new oxidative protocol is simple, highly efficient, and allows the practical synthesis of 1,2,4-thiadiazoles from various primary thioamides in good to excellent yields.
- Lee, Kieseung,Lee, Richard S.,Kim, Yong Hae
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supporting information
p. 1774 - 1779
(2020/06/01)
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- Method for synthesizing 1,2,4-thiadiazole derivative
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The invention relates to a method for synthesizing a 1,2,4-thiadiazole derivative, and belongs to the technical field of chemical preparation. The method comprises the following steps: taking and dissolving a phenylacetic acid compound and a benzylamidine hydrochloride compound in an organic solvent according to a mass ratio of (1-2):1, adding a catalyst, an oxidant and an alkaline medium, and stirring at 130-140 DEG C for 18-24 h to react in order to obtain the 1,2,4-thiadiazole derivative; and cooling, extracting, drying, evaporating under reduced pressure to remove the solvent, and carryingout column chromatography to obtain the pure product. The method for synthesizing thiadiazole has the following advantages: (1) the reaction conditions are mild, the product selectivity is high, andthe substrate expansion range is wide; and (2) the used raw materials are low in price and cost, and the reaction operation is simple, safe and convenient.
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Paragraph 0023-0076
(2020/05/01)
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- An alternatively metal-free synthesis of 1,3,5-triazines or 1,2,4-thiadiazoles from benzyl chlorides and benzylamines mediated by elemental sulfur
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An elemental sulfur mediated reaction of benzyl chlorides with benzylamines is developed, which allows the practical synthesis of valuable 1,3,5-triazines. This protocol that is metal free, ligand free, and uses inexpensive elemental sulfur as oxidant or raw material displays mild reaction conditions, a broad substrate scope and moderate to good yields. Moreover, the modified sulfur-mediated reaction system can also be used to synthesize 1,2,4-thiadiazoles, by simply switching the stoichiometry of sulfur powder from 0.75 equivalents to 5 equivalents.
- Zhang, Yurong,Liu, Yafei,Zhang, Jun,Gu, Ren,Han, Shiqing
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- Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation
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A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.
- Tian, Ting,Dong, An-Shun,Chen, Dan,Cao, Xian-Ting,Wang, Guannan
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p. 7664 - 7668
(2019/08/30)
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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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- One-pot synthesis of 3,5-disubstituted 1,2,4-thiadiazoles from nitriles and thioamides: Via I2-mediated oxidative formation of an N-S bond
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A simple and practical method for I2-mediated one-pot synthesis of 3-alkyl-5-aryl-1,2,4-thiadiazoles has been developed; the one-pot reaction includes sequential intermolecular addition of thioamides to nitriles, and intramolecular oxidative coupling of N-H and S-H bonds mediated by molecular iodine. Meanwhile the protocol uses readily available nitriles and thioamides as the starting materials, molecular iodine as the oxidant, and generates various 1,2,4-thiadiazoles in moderate to good yields with a wide array of functional groups. This method is an efficient approach for the synthesis of unsymmetrically disubstituted 1,2,4-thiadiazoles.
- Chai, Ling,Xu, Yuanqing,Ding, Tao,Fang, Xiaomin,Zhang, Wenkai,Wang, Yanpeng,Lu, Minghua,Xu, Hao,Yang, Xiaobo
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p. 8410 - 8417
(2017/10/19)
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- Multicomponent reactions (MCRs) of arylmethyl bromides, arylamidines and elemental sulfur toward unsymmetric 3,5-diaryl 1,2,4-thiadiazoles
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A base-promoted three-component reaction between arylmethyl bromides, arylamidines and elemental sulfur was developed, leading to unsymmetric 3,5-diaryl-1,2,4-thiadiazoles in moderate to good yields with chemical diversity and complexity. This procedure shows broad substrates scope by employing elemental sulfur and commercially available starting materials under transition-metal free conditions.
- Zhou, Zhen,Liu, Miaochang,Sun, Song,Yao, En,Liu, Suqin,Wu, Zhiwen,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
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supporting information
p. 2571 - 2573
(2017/06/13)
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- A Three-Component Approach to 3,5-Diaryl-1,2,4-thiadiazoles under Transition-Metal-Free Conditions
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A novel route is disclosed for the synthesis of 1,2,4-thiadiazoles starting from amidines, elemental sulfur, and 2-methylquinolines or aldehydes under transition-metal-free conditions. This three-component approach affords efficient and rapid access to 3,
- Xie, Hao,Cai, Jinhui,Wang, Zilong,Huang, Huawen,Deng, Guo-Jun
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supporting information
p. 2196 - 2199
(2016/06/01)
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- A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
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A novel and efficient process for the synthesis of 3,5-diaryl-1,2,4- thiadiazoles from aryl nitriles in 1-butyl-3-methylimidazolium bromide promoted by (NH4)2S and TCT-DMSO is described.
- Noei, Jalil,Khosropour, Ahmad Reza
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- Suzuki-Miyaura coupling reactions of 3,5-dichloro-1,2,4-thiadiazole
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3,5-Dichloro-1,2,4-thiadiazole was allowed to react with different arylboronic acids under different Suzuki-Miyaura coupling conditions: at room temperature 5-aryl-3-chloro-1,2,4-thiadiazoles were obtained and at toluene reflux temperature the products we
- Farahat, Abdelbasset A.,Boykina, David W.
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p. 2437 - 2448
(2012/10/30)
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- Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
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Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).
- Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
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p. 510 - 520
(2012/03/10)
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- Novel Conversion of 6H-1,3,5-Oxathiazine S-Oxides into 5-Membered Heterocyclic Compounds
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5H-1,2,4-oxathiazoles were efficiently synthesized from 6H-1,3,5-oxathiazine S-oxides by thermal cycloreversion of the substrates and the products were effectively converted into 1,2,4-thiadiazoles.
- Rafiqul, Islam Md.,Shimada, Kazuaki,Aoyagi, Shigenobu,Takikawa, Yuji,Kabuto, Chizuko
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p. 175 - 186
(2007/10/03)
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- Novel generation and ring closure of 1,3-thiaza-1,3-butadiene S-oxides through thermal cycloreversion of 6H-1,3,5-oxathiazine S-oxides
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Heating of 6H-1,3,5-oxathiazine S-oxides efficiently afforded 1,2,4-oxathiazoles through the mechanism involving thermal cycloreversion of the substrates and the subsequent ring closure of the intermediary 1,3-thiaza-1,3-butadiene S-oxides.
- Shimada, Kazuaki,Rafiqul, Islam Md.,Sato, Masanobu,Aoyagi, Shigenobu,Takikawa, Yuji
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p. 2517 - 2519
(2007/10/03)
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- Selenium heterocycles. XLIII. Syntheses of 3,5-diaryl-1,2,4- thiadiazoles and 3,5-diaryl-1,2,4-selenadiazoles
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Starting from readily available α-arylsulfonyl-α- bromoacetophenones 2 a series of 3,5-diaryl-1,2,4-thiadiazoles and 3,5-diaryl-1,2,4-selenadiazoles were prepared in moderate yield. Reaction of compounds 2 with thiourea or selenourea gave 2-amino-5-arylsu
- Shafiee,Ebrahimzadeh,Maleki
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p. 901 - 903
(2007/10/03)
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- Photoinduced molecular rearrangements. The photochemistry of 1,2,4-oxadiazoles in the presence of sulphur nucleophiles. Synthesis of 1,2,4-thiadiazoles
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The photochemistry of some 1,2,4-oxadiazoles in the presence of sulphur nucleophiles has been investigated. Irradiation of the 5-amino-3-phenyl- and 3,5-diphenyl-1,2,4-oxadiazole at λ = 254 nm in methanol in the presence of sodium hydrogen sulphide or thiols gave a photo-induced redox reaction at the ring O-N bond, leading to the corresponding N-substituted benzamidines. By contrast, irradiation of the 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioureas or thiocarbamates, essentially gave 3-phenyl-5-substituted 1,2,4-thiadiazoles, which presume an N-S bond formation between the ring-photolytic species and the sulphur nucleophile. In turn, irradiation of the same 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioamides again afforded the redox reaction; in addition, amounts of 3-phenyl-5-substituted-1,2,4-thiadiazoles were also formed. Some mechanistic considerations are reported and synthetic methodologies leading to 1,2,4-thiadiazoles are emphasized.
- Vivona, Nicolo,Buscemi, Silvestre,Asta, Stefano,Caronna, Tullio
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p. 12629 - 12636
(2007/10/03)
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- REACTION OF SULFUR WITH ORGANIC COMPOUNDS. XXVII. REACTION OF SULFUR WITH BENZYLAMINE
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The reaction of sulfur with benzylamine in a sealed tube at 25 deg C leads to a mixture of N-benzylidenebenzylamine, dibenzylaminohexasulfane, dibenzylaminooctasulfane, N-benzylazacyclononasulfane, and N-thiobenzoylazacyclononasulfane. At 180 deg C toluene, benzonitrile, benzylideneamine, phenylmethanethiol, thiobenzamide, E- and Z-stilbene, bibenzyl, dibenzyl sulfide, and dibenzyl disulfide, N-benzylthiobenzamide, 3,5-diphenyl-1,2,4-thiadiazole, and 2,4,6-triphenyl-1,3,5-triazine are formed.
- Pzhevotskii, K.,Voronkov, M. G.,Pzhevotskaya, L.,Malinskii, E.,Usov, V. A.
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p. 472 - 475
(2007/10/02)
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- Benzenetellurinic Mixed Anhydrides as Mild Oxidizing Agents
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Three benzenetellurinic mixed anhydrides. i. e. benzenetellurinyl acetate, trifluoroacetate, and trifluoromethanesulfonate, have been found to be mild oxidizing agents for various substrates such as thiol, phosphine, acyloin, α-hydroxy ester, catechol, hydroquinone, thiourea, and thioamide.The reactions towards the last two substrates are highly chemoselective, depending on both the reagent and substrate.
- Fukumoto, Takahiro,Matsuki, Toshiaki,Hu, Nan Xing,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
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p. 2269 - 2272
(2007/10/02)
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- Synthetic applications and spectroscopic investigations of the (NSCl)3-SO2Cl2 system
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Solutions of (NSCl)3 in the presence of excess SO2Cl2 behave as a source of the synthetic equivalent "NSCl3" in reactions with methacrylonitrile or thioacetamide to give 4-cyanoisothiazole (78percent) or 5-methyl-1,3,2,4-dithiadiazolium chloride (63percen
- Apblett, Allen,Chivers, Tristram
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p. 650 - 654
(2007/10/02)
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- PHOTOREACTION OF BENZENECARBOTHIOAMIDE WITH OLEFINS. SYNTHESES OF ISOTHIAZOLE DERIVATIVES AND PHENONES
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Photoreaction of benzenecarbothioamide (1) in the presence of olefins gave isothiazole derivatives (10, 12, and 13) and 3,5-diphenyl-1,2,4-thiadiazole (11) under aerobic conditions, whereas under nitrogen atmosphere gave phenones (3 and 4).
- Oda, Kazuaki,Machida, Minoru
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p. 983 - 991
(2007/10/02)
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- Preparation and reactions of 5-Aryl-1,4,2-dithiazolium salts
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S-Thioaroylsulfenamides (ArCSSNH2), formed by reaction of ArCSS-Na+ with hydroxylamine-O-sulfonic acid, were aroylated or acylated to give N-aroyl- or N-acyl-S-thioaroylsulfenamides, respectively, which were then cyclized with dehydration to afford 3-substituted 5-aryl-1,4,2-dithiazolium salts. The behavior of 3,5-diphenyl-1,4,2-dithiazolium Perchlorate toward nucleophiles such as active methylene and amino compounds was studied systematically. The reaction can be classified into two cases depending on fission modes of initial adducts, i.e., ring opening-ring closure reaction (Path B) and fragmentation of dithiazole ring (Path C), and in some cases the initial adducts were isolated.
- Yonemoto, Katsumi,Shibuya, Isao,Tsuchiya, Tohru,Masahiko Yasumoto,Taguchi, Yoichi
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p. 2933 - 2937
(2007/10/02)
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- Oxidative heterocyclization using diethyl azodicarboxylate
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The reactions of amidinothioureas, imidoylthioureas, thioacylamidines, O-methyl-1-aryl-2-thioisobiurets, and 1-aryl-isodithiobiurets with diethyl azodicarboxylate (DEAD, diethyl diazenedicarboxylate) gave the corresponding thiadiazoles by the oxidative cy
- Kihara,Kabashima,Uno,Okawara,Yamasaki,Furukawa
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p. 1020 - 1023
(2007/10/02)
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- HETEROCYCLIZATION OF DERIVATIVES OF THIONCARBOXYLIC ACIDS TO 1,3,4-THIADIAZOLES UNDER THE ACTION OF TERT-BUTYL HYPOCHLORITE
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A method for synthesis of 2-alkyl-5-aryl- and 2,5-diaryl-1,3,4-thiadiazoles by successive reaction of thioamides with tert-butyl hypochlorite and benzothiohydrazides was developed.The first step in the formation of 1,3,4-thiadiazoles consists of oxidation
- Demchuk, D. V.,Lutsenko, A. I.,Troyanskii, E. I.,Nikishin, G. I.
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p. 1690 - 1695
(2007/10/02)
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- Indirect Electrolytic Oxidation of Thioamides Using Organotellurium as a Mediator
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Bis(p-methoxyphenyl) telluride (1) electrochemically reacted with supporting electrolytes such as tetrabutylammonium acetate and tetraethylammonium tosylate under anhydrous conditions to give tellurium(IV) diacetate 2a and ditosylate 2b, respectively.On the other hand, 1 was electrolyzed in the presence of water to give telluroxide 3.It has turned out that the tellurium compounds 2a and 2b like telluroxide 3 are mild oxidizing agents, but 2b behaves differently in a reaction towards thioamide.Thus 2a and 3 converted it into nitrile, while 2b did it into 1,2,4-thiadiazole.An indirect electrolytic oxidation of thioamides with 1 as a mediator was examined under various conditions.As a result, nitriles or 1,2,4-thidiazoles could be chemoselectively formed, depending on the intermediacy of 2a or 3 as an active species for the formed and 2b for the latter.
- Matsuki, Toshiaki,Hu, Nan Xing,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
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p. 2117 - 2122
(2007/10/02)
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- SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND. XI. REACTION OF SELENIMIDES WITH THIOLS AND THIOAMIDES
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The oxidizing power of chalcogen imides in reactions with thiols and thioamides increases in the order S +-N- bond during the substitution of the phenyl radicals attached to the selenium atom by the electron-donating benzyl groups.
- Naddaka, V. I.,Avanesyan, K. V.,Cherkinskaya, M. L.,Minkin, V. I.
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p. 2245 - 2250
(2007/10/02)
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- Synthesis of Mesoionic 1,2,3,5-Thiatriazoles
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On treatment of 1-amino-1-alkyl-3-arylguanidines with thionyl chloride in pyridine, yellow complexes between mesoionic 1,2,3,5-thiatriazoles (anhydro-3-alkyl-4-arylamino-1,2,3,5-thiatriazolium hydroxides) and pyridinium chloride are formed.The strongly coloured mesoionic compounds are liberated by treatment with base (aryl = phenyl, 4-methylphenyl, 2-chlorophenyl; alkyl = methyl).On attempted synthesis of 5-phenyl-1,2,3,5-thiatriazole by treatment of benzamidrazone with thionyl chloride in pyridine, spontaneous evolution of nitrogen and formation of benzonitrile and sulfur were observed.
- Felding, Gitte,Holm, Arne
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- Organic Heterocyclothiazenes. Part 2. Reaction of Tetrasulphur Tetranitride with Phenylacetylene and Diphenylacetylene
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The reaction of S4N4 with diphenylacetylene in boiling toluene has been found to give 3,4-diphenyl-1,2,5-thiadiazole (1) as the major product and 3,5-diphenyl-1,4,2,6-dithiadiazine (4), a new heterocyclic system, as a minor product.The same reaction with
- Daley, Stephen T. A. K.,Rees, Charles W.
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p. 207 - 210
(2007/10/02)
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- Nitrile Sulphides. Part 3. Thermal Fragmentation of 1,3,4-Oxathiazoles: Formation of Nitrile Sulphides in a Retro-1,3-dipolar Cycloaddition Reaction
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On thermolysis at ca. 160 gradC 1,3,4-oxathiazoles undergo retro-1,3-dipolar cycloaddition forming nitrile sulphides and carbonyl-containing fragments.The nitrile sulphides either decompose to sulphur and nitriles or are trapped as their 1,3-dipolar cycloadducts in the presence of dipolarophiles (dimethyl acetylenedicarboxylate, ethyl cyanoformate, benzonitrile, ethyl propiolate).Similar ratios (1.32, l.34, 1.33, 1.31) of 4- and 5-ethoxycarbonyl-3-(p-methoxyphenyl)isothiazole obtained from four sources of p-methoxybenzonitrile sulphide with ethyl propriolate provide strong evidence for product formation from a discrete intermediate nitrile sulphide rather than via direct interaction of precursor with dipolarophile. 2-Dichloromethylene-1,3,4-oxathiazoles, prepared by dehydrochlorination of 2-trichloromethyloxathiazoles, prepared by dehydrochlorination of 2-trichlorometyloxathiazoles, likewise fragment to nitrile sulphides, but attempts to trap dichloroketene were unsuccessful.
- Paton, R. Michael,Robertson, Fiona M.,Ross, John F.,Crosby, John
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p. 1517 - 1522
(2007/10/02)
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- Cycloaddition Reaction of 1,4,2-Dithiazole-5-thiones
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1,4,2-Dithiazole-5-thiones can act either as the 2-atom or the 3-atom component in 2+3-cycloadditions.Benzonitrile N-phenylimine, generated in situ by dehydrochlorination of N-phenylbenzohydrazonoyl chloride, reacts at the exocyclic C=S double bond forming the thiadiazolethione (17) and the spiro compound (18) by collapse of the initial cycloadduct (19) and further 1,3-dipolar cycloaddition.The corresponding reaction with ethyl azidoformate yields a 5-ethoxycarbonylimino-1,4,2-dithiazole.On treatment-with dimethyl acetylenedicarboxylate and ethylcyanoformate the dithiazolethione itself acts as a 1,3-dipole forming 1,3-dithiole and 1,4,2-dithiazolethiones with expulsion of a nitrile fragment.
- Greig, Derek J.,McPherson, Michael,Paton, Michael R.,Crosby, John
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p. 1205 - 1208
(2007/10/02)
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- Convenient Preparations of 3,5-Disubstituted 1,2,4-Thiadiazoles by Oxidative Dimerization of Thioamides
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3,5-Disubstituted 1,2,4-thiadiazoles 2 were prepared by reaction of thioamides 1 with DMSO in the presence of such an electrophilic reagent as 1-methyl-2-chloropyridinium iodide, benzoyl chloride, acetyl chloride, hydrochloric acid, or trimethylsilyl chloride in organic solvents at room temperature in high yields.Thiadiazoles 2 were also obtained by reaction of 1 with NBS at room temperature in high yields.Thioamide S-oxides reacted with electrophilic reagents at room temperature to give the corresponding thiadiazoles 2 in high yields.
- Takikawa, Yuji,Shimada, Kazuaki,Sato, Katsuyuki,Sato, Shinichi,Takizawa, Saburo
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p. 995 - 999
(2007/10/02)
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- Reactions of Tetrasulphur Tetranitride with Alkynes; 1,4,2,6-Dithiadiazines and 1,3,2-Dithiazoles
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Reaction of S4N4 with diphenylacetylene and phenylacetylene gives two new, thermally stable heterocyclic systems, the 1,4,2,6-dithiadiazine (3) and the 1,3,2-dithiazolylimine (7), respectively, as minor products; these structures, determined by X-ray diff
- Daley, Stephen T. A. K.,Rees, Charles W.,Williams, David J.
-
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- The Triethylamine Catalyzed Reaction of N,N-Disubstituted Thioamide-Bromine Adducts With Unsubstituted Thiobenzamide
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The reaction of N,N-disubstituted thioamide-bromine adducts with unsubstituted thioamide, followed by treatment with triethylamine, affords novel N'-thiobenzoylamidines along with smaller amounts of secondary products.A mechanism is proposed for the formation of the amidines.The results give an insight into the initial steps of the mechanism by which thioamides are converted into 1,2,4-thiadiazoles.
- Corsaro, Antonino,Compagnini, Anna,Perrini, Giancarlo,Purrello, Giovanni
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p. 897 - 900
(2007/10/02)
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- PHOTOCYCLOADDITION OF ARYLCARBOTHIOAMIDES WITH UNSATURATED SYSTEMS. SYNTHESIS OF 3,5-DIARYL-1,2,4-THIADIAZOLES AND 3-ARYL-4,4,5,5-TETRAMETHYLISOTHIAZOLINES VIA PHOTOGENERATED NITRILE SULFIDES
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On irradiation arylcarbothioamides (1) undergo, in the absence of oxygen, the Paterno-Buechi reaction with olefins followed by cleavage, whereas under aerobic conditions the photoreaction proceeds to give 4 and 5 probably via nitrile sulfide intermediates
- Machida, Minoru,Oda, Kazuaki,Kanaoka, Yuichi
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p. 409 - 410
(2007/10/02)
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- REACTION OF N-CHLORO-N'-ARYLSULFONYL- AND N'-BENZOYLBENZAMIDINES WITH SULFUR AND SULFUR DICHLORIDE
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N-(N'-Arylsulfonylbenzimidoyl)dichlorosulfimides are obtained in the reaction of N-chloro-N'-arylsulfonylbenzamidines with sulfur or sulfur dichloride.N-Chloro-N'-benzoylbenzamidine reacts with sulfur dichloride in the presence of pyridine to form N-(N'-benzoylbenzimidoyl)dichlorosulfimide.Thermolysis of the latter gives 1,3,5-triphenyl-sym-triazine.When N-chloro- or N,N-dichloro-N'-benzoylbenzamidines are heated with an excess of sulfur dichloride, 2,4-diphenyl-1,3,5-thiadiazole is formed.The reaction of N-chloro-N'-benzoylbenzamidine with thionyl chloride gives N-(N'- benzoylbenzimidoyl)sulfinylamine, which decomposes with the formation of 1,3,5-triphenyl-sym-triazine when heated in inert solvents.
- Borovikova, G. S.,Levchenko, E. S.,Borovik, E. I.,Darmokhval, E. A.
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p. 171 - 176
(2007/10/02)
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- REACTION OF SULFUR DICHLORIDE WITH NITRILE IN THE PRESENCE OF LEWIS ACID FORMING 1,2,4-THIADIAZOLE.
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Formation of 3,5-disubstituted 1,2,4-thiadiazoles by the reaction of sulfur dichloride with nitriles in the presence of a Lewis acid was found. For example, 3,5-diphenyl-1,2,4-thiadiazole was obtained with its chlorinated products, 3-o-chlorophenyl-5-phen
- Komatsu,Shibata,Ohshiro,Agawa
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p. 180 - 183
(2007/10/02)
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- Sulfur Nitride in Organic Chemistry. 9. The Reaction of Tetrasulfur Tetranitride with Benzyl Ketones. Preparation of 3,4-Disubstituted-1,2,5-thiadiazoles
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The reaction of tetrasulfur tetranitride (1) with various aryl and benzyl ketones (2a-o), oxindole (11), benzyl α-pyridyl ketone (12) and α-phenacylpyridine (13) afforded the corresponding 1,2,5-thiadiazoles (3a-n, 11 and 14).The scope and limitations of the above reaction were investigated and the evidences suggesting the radical anion mechanism are presented.
- Mataka, Shuntaro,Hosoki, Akira,Takahashi, Kazufumi,Tashiro, Masashi
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p. 1681 - 1685
(2007/10/02)
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