- Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea
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An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.
- Bagherzadeh, Nastaran,Sardarian, Ali Reza,Inaloo, Iman Dindarloo
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supporting information
p. 11852 - 11858
(2021/07/12)
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- Synthesis of primary thiocarbamates by silica sulfuric acid as effective reagent under solid-state and solution conditions
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A simple and efficient method for the conversion of alcohols and phenols to primary O-thiocarbamates and S-thiocarbamates in the absence of solvent (solvent-free condition) using silica sulfuric acid (SiO2OSO 3H) as a solid acid is described. The products are easily distinguished by IR, NMR and X-ray data. X-ray data of the compounds reveal a planar trigonal orientation of the NH2 nitrogen atom with the partial C,N double-bond character and the CS or CO groups in synperiplanar position with CarylO and CalkylS moieties, respectively. Moreover, the OCSNH2 group which is perpendicular to the plane of the benzene ring in 1c and the central thiocarbamate SCONH2 group in 2b are essentially planar.
- Modarresi-Alam, Ali Reza,Inaloo, Iman Dindarloo,Kleinpeter, Erich
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p. 156 - 162,7
(2012/12/12)
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- Synthesis and structure of substituted 5-phenoxy-1,2,4-dithiazole-3-ones
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Seven new substituted 5-phenoxy-1,2,4-dithiazole-3-ones were prepared in modest yield (53-76%) from corresponding O-phenyl thiocarbamates and chlorocarbonylsulfenyl chloride in dry ether at-10 °C. All of the compounds were characterized by NMR and elemental analysis and some of them by X-ray diffraction. Preliminary kinetic measurements showed that the parent 5-phenoxy-1,2,4-dithiazole-3-one is a very efficient sulfurizing agent toward triphenyl phosphite. Copyright
- Ponomarov, Oleksandr,Padelkova, Zdenka,Hanusek, Jiri
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p. 1225 - 1228
(2012/01/04)
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- Agonists and antagonists to nicotine as smoking deterents
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Agonists and antagonists to nicotine are used as smoking deterrents.The nicotinic antagonists have the following structural requirements:(1) Aromatic, cycloalkyl, and heterocyclic carbamic acid esters of di- and trialkylaminoalkyl alcohols.(2) Aromatic, cycloalkyl, and heterocyclic thiocarbamic acid esters of di- and trialkylaminoalkyl alcohols.(3) Aromatic, cycloalkyl, and heterocyclic carboxylic acid esters of di- and trialkylaminoalkyl alcohols.(4) Aromatic, cycloalkyl, and heterocyclic carboxylic acid esters of heterocyclic amino alcohols.(5) Lobelia alkaloids: lobeline, lobelanine, and lobelanidine.The nicotinic agonists (nicotine-like) have the following structural requirements:(1) methylcarbamic acid esters of di- and trialkylaminoalkyl alcohols.(2) methylthiocarbamic acid esters of di- and trialkylaminoalkyl alcohols.
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