- A new one-pot synthesis of thiocarbamates from isocyanates and disulfides in the presence of Zn/AlCl3 system
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A novel method has been developed for the synthesis of S-alkyl(aryl) thiocarbamates. The route involves, first, the formation of zinc thiolates by reductive cleavage of disulfides in the presence of Zn/AlCl3 system; then subsequent reaction of
- Movassagh, Barahman,Zakinezhad, Yousef
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- Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates
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A new route to S-alkylcarbamothioates is disclosed. In a first step, N-(2-aminophenyl)-4-methyl-thiazolin-2-thione is transformed into a mono- or disubstituted urea at nitrogen, and then in a second step, alkylated at sulfur. The resulting salts, after treatment with a base, gave S-alkylcarbamothioates in high isolated yields together with 3-methyl[1,3]thiazolo[3,2-a]benzimidazole under very mild conditions.
- Doukara, Abdallah Larbi,Mehdid, Mohammed Amine,Djafri, Ayada,Andreoli, Federico,Vanthuyne, Nicolas,Roussel, Christian
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experimental part
p. 1852 - 1858
(2010/04/04)
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- A selenium-catalysed synthesis of thiocarbamates from nitroarenes, carbon monoxide and thiols under mild conditions
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An improved method for the selenium-catalysed synthesis of thiocarbamates under mild conditions has been developed. With acetone as solvent, the one-pot selenium-catalysed carbonylation of nitroarenes and thiols with carbon monoxide proceeds smoothly at atmospheric pressure and ambient temperature.
- Zhang, Xiao-Peng,Lu, Shi-Wei
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experimental part
p. 589 - 591
(2009/08/15)
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- One-pot direct synthesis of thiocarbamates from aniline, carbon monoxide, and thiols catalyzed by selenium
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Catalyzed by selenium, oxidative carbonylation of aniline and thiols with carbon monoxide and oxygen affords the corresponding thiocarbamates mostly in moderate to good yields under solvent-free conditions at ambient temperature. Copyright Taylor & Franci
- Zhang, Xiaopeng,Lu, Shiwei
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p. 3291 - 3299
(2008/02/12)
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- A novel one-pot solvent-free, triethylamine-assisted, selenium-catalyzed synthesis of thiocarbamates from nitroarenes, carbon monoxide, and thiols
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A novel one-pot solvent-free synthesis of a series of thiocarbamates is reported. Nitroarenes, carbon monoxide, and thiols are the starting materials, with cheap element selenium as catalyst; this method offers a simple access to thiocarbamates mostly in moderate to good yields. The selenium catalyst can be easily recovered and recycled. Georg Thieme Verlag Stuttgart.
- Zhang, Xiaopeng,Lu, Shiwei
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p. 1535 - 1538
(2007/10/03)
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- Potent inhibitory effects of N-aryl S-alkylthiocarbamate derivatives on the dopa oxidase activity of mushroom tyrosinase
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This study reports the potent inhibitory effect of N-aryl S-alkylthiocarbamate derivatives on mushroom tyrosinase (MT) activity. N-Aryl S-alkylthiocarbamate derivatives were found to exhibit a potent inhibitory effect on the dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Most of the N-aryl S-alkylthiocarbamate derivatives (compounds from A to J) exhibited higher inhibitory effects than kojic acid (IC50=318 μm), a well known tyrosinase inhibitor. Tyrosinase was the most inhibited by S-phenetyl N-phenylthiocarbamate (compound E, IC50=7.25 μM), and this inhibition was 44 times stronger than that of kojic acid. Compound E exhibited 95.0% of inhibition at 100 μM. A kinetic study of MT inhibition by compound E using the Lineweaver-Burk plots analysis was performed. And the kinetics profiles observed suggest that compound E competitively inhibits MT.
- Lee, Kun Ho,Koketsu, Mamoru,Choi, Sang Yoon,Lee, Kang Jin,Lee, Pyeongjae,Ishihara, Hideharu,Kim, Sun Yeou
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p. 747 - 749
(2007/10/03)
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- A new and facile route for the synthesis of thiocarbamates from aniline, carbon monoxide, and thiols mediated by selenium
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A new and facile route for the synthesis of thiocarbamates was reported. Mediated by selenium, aniline reacts very readily with carbon monoxide and thiols in the presence of triethylamine, to afford the corresponding thiocarbamates mostly in moderate to excellent yields under mild reaction conditions. Selenium can be easily recovered and recycled. Copyright
- Zhang, Xiaopeng,Lu, Shiwei
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p. 606 - 607
(2007/10/03)
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- Synthesis of N-aryl S-alkylthiocarbamates
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The synthesis of N-aryl S-alkylthiocarbamates was discussed. The carbamates were synthesized by reactions of isocyanates with LiAlHSH and then with alkyl halides. Melting points were determined by using Yanagimoto micromelting point apparatus and were corrected. It was found that LiAlHSH behaved in a similar fashion as LiAlHSeH.
- Koketsu, Mamoru,Kobayashi, Chikashi,Ishihara, Hideharu
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p. 374 - 378
(2007/10/03)
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- The Kinetics and Mechanism of the Thallium(III) Ion-promoted Hydrolysis of Thiolurethanes in Aqueous Solution. A Metal Ion-promoted Elimination
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The hydrolysis of thiolurethanes R1C6H4NHCOSC6H4R2 (1), in dilute aqueous perchloric acid, under conditions where the spontaneous hydrolysis is negligible, is promoted by Ti3+ ions.The organic products are the corresponding anilinium ion and the thalium salt of the thiophenol.The effects of substituent changes (R1,R2) of changes in +>, temperature, ionic strength, and of replacement of the NH proton by Me, are all compatible with hydrolysis occurring by elimination-addition mechanisms via the isocyanate as a reactive intermediate; thalium ion-promoted E1 cb and E2 routes are implicated.In effect the elimination-addition type of mechanism which is important for these esters at higher pH has been made available at low pH by complexation with Tl3+ ions.With the thiolurethanes RC6H4NHCOSEt, (2) which are less susceptible to the spontaneous and base-catalysed elimination-addition mechanisms of hydrolysis than are thiolurethanes (1), the presence of Tl3+ ions can also lead to promoted hydrolysis via elimination, but an AAc1-like route (with Tl3+ taking the role of H+) seems to be available to the N-Me derivatives.
- Satchell, Derek P. N.,Satchell, Rosemary S.,Wassef, Wasfy N.
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p. 1199 - 1202
(2007/10/02)
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- N-Nitroso Compounds. IV. Reaction of N-Nitrosourea with Thiol. A New Synthesis of Thiocarbamic S-Esters
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Thirteen thiocarbamic S-esters have been prepared in good yield by the reaction of thiol with substituted N-methyl-N-nitrosourea in anhydrous acetonitrile.
- Yoshida, Kitaro,Isobe, Masayoshi,Yano, Kazuyuki,Nagamatsu, Kazuo
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p. 2143 - 2144
(2007/10/02)
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- New Heterocyclic Compounds : 5-Oxo/thio-4-aryl-2-phenylimino-1,3,4-dithiazolidines
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5-Oxo/thio-4-aryl-2-phenylimino-1,3,4-dithiazolidines (VI and IX) have been prepared by reaction of S-chloro-N-phenylisothiocarbamoyl chloride and triethylamine salts of arylthiocarbamic acids and aryldithiocarbamic acids respectively.VI and IX when boiled with benzylamine give the same product (XI).The structures of all these products have been assigned on the basis of chemical transformations and IR data.Probable mechanisms of these reactions are also suggested.
- Jadhav, R. T.,Nimdeokar, N. M.,Paranjpe, M. G.
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p. 970 - 974
(2007/10/02)
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