- ISOTHIOCYANATE PRODUCTION METHOD, COMPOSITION FOR TRANSPORTING AND STORING N-SUBSTITUTED O-SUBSTITUTED THIOCARBAMATE, AND ISOTHIOCYANATE COMPOSITION
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The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.
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- Contrasting Reactivity of CS2 with Cyclic vs. Acyclic Amidines
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The interaction between carbon dioxide (CO2) and amidines such as 1,8-diazabicyclo[5.4.0]undecane (DBU) has been extensively studied, but the reaction of isovalent CS2 with such bases has been largely ignored, apart from a single crystallography report. Acyclic acetamidines are cleaved by CS2 at room temperature to give an isothiocyanate and a thioacetamide. Because the pathway to that cleavage involves a rotation that is difficult for cyclic amidines, the reaction of CS2 with cyclic amidines produces an entirely different product: a cyclic carbamic carboxylic trithioanhydride structure. The path to that product involves sp3 C-H activation leading to the formation of a new C-C bond at a carbon α to the central carbon of the amidine group. Alkylation and ring-opening of the cyclic carbamic carboxylic trithioanhydride has also been demonstrated under ambient conditions.
- Ang, M. Trisha C.,Phan, Lam,Alshamrani, Aliyah K.,Harjani, Jitendra R.,Wang, Ruiyao,Schatte, Gabriele,Mosey, Nicholas J.,Jessop, Philip G.
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p. 7334 - 7343
(2015/11/25)
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- ISOTHIOCYANATE PRODUCTION METHOD, COMPOSITION FOR TRANSPORTING AND STORING N-SUBSTITUTED O-SUBSTITUTED THIOCARBAMATE, AND ISOTHIOCYANATE COMPOSITION
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The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.
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- Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: Facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides
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Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.
- Li, Tian-Tian,Song, Xiang-Hai,Wang, Mei-Shuang,Ma, Ning
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p. 40054 - 40060
(2014/12/10)
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- Synthesis and structure-activity relationships of aliphatic isothiocyanate analogs as antibiotic agents
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Isothiocyanates (ITCs) are one of the many classes of breakdown products of glucosinolates found in plants and exhibit biologic activity against various pathogens. In this work, aliphatic isothiocyanates were prepared and the antimicrobial activities against plant pathogenic fungi and bacteria were tested to understand the structure-activity relationships. The results indicated that longer-chain derivatives exert a steric inhibition on toxicity of ITCs against Rhizoctonia solani because of steric hindrance and the order of the eight aliphatic ITCs was ethyl > n-propyl > methyl > n-hexyl > n-octyl > n-butyl > n-heptyl > n-pentyl. Because the hydrophobicity of ITCs was enhanced by increasing alkyl chain length, the antibacterial activity of ITCs against Erwinia carotovora was moderately intense with an increase in hydrophobicity and the order was n-octyl > n-pentyl > n-heptyl > n-hexyl > n-propyl > n-butyl > methyl > ethyl. The present study revealed that some of the compounds exhibited promising antimicrobial activity and could be used as an acceptable alternative to the traditional synthetic fungicides for controlling R. solani and E. carotovora.
- Li, Deguang,Shu, Yanan,Li, Pingliang,Zhang, Wenbing,Ni, Hanwen,Cao, Yongsong
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p. 3119 - 3125
(2013/07/11)
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- A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
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A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS2 followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.
- Sun, Nan,Li, Bin,Shao, Jianping,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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experimental part
p. 61 - 70
(2012/04/04)
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- Bronchorelaxing compounds
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A compound of the general formula (I) including its pharmaceutically acceptable acid addition salts wherein A is CHR9, wherein R9 is H, C1-C6 alkyl; n is 1-3; B is CHR10, wherein R10 is H, C1-C6 alkyl; m is 1 or 2; D is O or S or optionally NR16, wherein R16 is H, C1-C6 alkyl or C2-C6 acyl; E is CR11R12 or NR13, wherein R11 and R12 are, independent of each other, H or C1-C6 alkyl, R13 is H or C1-C6 alkyl; F is C1-C18 alkyl which may be mono- or di-unsaturated and/or substituted, is useful in treating and preventing pulmonary disease characterized by bronchoconstriction. Also disclosed are pharmaceutical compositions comprising the compound and methods for their manufacture.
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Page/Page column 16
(2010/02/13)
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- Efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding thiocyanates with in-situ-generated Ph3P(SCN) 2
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Immediate and efficient one-pot conversion of tetrahydropyranyl (THP) ethers to their corresponding thiocyanates by in-situ-generated Ph 3P(SCN)2 is described. Primary and secondary alkyls and also benzylic THP ethers are converted to their corresponding thiocyanates in excellent yields at room temperature by this method. Copyright Taylor & Francis Inc.
- Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza
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p. 2093 - 2096
(2007/10/03)
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- Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur
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Rhodium complexes RhH(PPh3)4 and Rh(acac)(CH 2CH2)2 catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.
- Arisawa, Mieko,Ashikawa, Masanori,Suwa, Atsushi,Yamaguchi, Masahiko
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p. 1727 - 1729
(2007/10/03)
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- Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur
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The direct molybdenum-catalyzed sulfuration of a variety of isonitriles with elemental sulfur or propene sulfide as sulfur donors affords the corresponding isothiocyanates in good yields and under mild reaction conditions. A catalytic cycle is suggested, in which the molybdenum oxo disulfur complex operates as the active sulfur-transferring species. A novel adduct between the isonitrile and the molybdenum complex has been characterized by X-ray analysis and its association constant determined by UV-vis spectroscopy, but this adduct appears not to be involved in the sulfur-transfer process.
- Adam, Waldemar,Bargon, Rainer M.,Bosio, Sara G.,Schenk, Wolfdieter A.,Stalke, Dietmar
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p. 7037 - 7041
(2007/10/03)
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- Synthesis of isothiocyanates by reaction of amides with carbon disulfide in the presence of solid potassium carbonate/sodium hydroxide mixture
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Readily available N-monosubstituted trifluoroacetamides are transformed into isothiocyanates in good yield by reaction, at room temperature, with carbon disulfide in acetonitrile in the presence of anhydrous sodium hydroxide/potassium carbonate basic mixture.
- Albanese,Penso
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p. 1001 - 1002
(2007/10/02)
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- A Method for the Simultaneous Preparation of Alkyl Isothiocyanates and Thiols
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Aus primaeren Alkylaminen wurden Ethyl-, Butyl-, Isobutyl- und n-Dodecyldithiocarbamate 2 hergestellt.Letztere lassen sich leicht zu den Isothiocyanaten 3 und Thiolen 4 pyrolisieren.Die Massenspektren der Ester sowie deren Pyrolyseprodukte wurden gemessen.
- Blotny, Grzegorz
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p. 1927 - 1932
(2007/10/02)
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