- Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination
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An efficient inexpensive cobalt(iii)-catalyzed intermolecular amidation of N,N-dialkyl thiobenzamides with 1,4,2-dioxazol-5-ones via C-H bond activation is described. The reaction proceeds with high functional group tolerance under external oxidant free conditions, providing a straightforward approach for the direct modification of thioamide derivatives, which are prevalent organic motifs found in vital biological and pharmaceutical molecules. This journal is
- Gao, Pengpeng,Zhang, Xiaohui,Zheng, Qing-Zhong
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supporting information
p. 10332 - 10336
(2021/12/17)
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- Method for preparing aryl thioamide compound
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The invention discloses a method for preparing an aryl thioamide compound. The method comprises the following steps: under the protection of inert gas, performing stirring to react for 6-12 hours at the reaction temperature of room temperature to 60 DEG C by taking aryl methanol as a substrate, sublimed sulfur as a sulfur source, an alkali metal complex formed by combining alkali metal salt and ligand as a catalyst, alkali as an accelerant, formamide as a solvent and an amine source; and carrying out post-treatment on the reaction product to obtain the aryl thioamide compound. According to theinvention, cheap and easily available aryl methanol is used as a substrate for three-component reaction to prepare the corresponding thioamide compound; the method for preparing the aryl thioamide compound has the technical advantages of simple technological process, high yield, less pollution, safety, environmental protection, greenness, mildness and the like.
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Paragraph 0050-0052
(2021/03/31)
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- Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF
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We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.
- Zhang, Jin,Liu, Ying,Jia, Qiangqiang,Wang, Yue,Ma, Yangmin,Szostak, Michal
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supporting information
p. 6884 - 6890
(2020/09/15)
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- A convenient one-pot preparation of N-substituted thioamides
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A convenient one-pot preparation of N-substituted thioamides from acyl halides, amines and H2O/PSCl3/Et3N in good to excellent yield has been reported through a solvent-free, microwave assisted method.
- Pandey, Lokesh Kumar,Pathak, Uma,Mazumder, Avik,Mathura, Sweta
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experimental part
p. 1225 - 1228
(2010/12/20)
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- Mild method for the conversion of amides to thioamides
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Aqueous ammonium sulfide was found to be an ideal substitute for hydrogen sulfide for the thiolysis of activated amides. High yields of the corresponding thioamides were obtained for a broad range of substrates, using two different procedures that are both operationally simple and inexpensive, as well as amenable to large-scale preparation. Preliminary results indicate that aqueous ammonium sulfide may also replace hydrogen sulfide in the synthesis of thionoesters from amides.
- Charette, Andre B.,Grenon, Michel
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p. 5792 - 5794
(2007/10/03)
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- Effect of amine nature on reaction mechanism: Aminolyses of O-4-nitrophenyl thionobenzoate with primary and secondary amines
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Pseudo-first-order rate constants (kobs) have been measured spectrophotometrically for reactions of O-4-nitrophenyl thionobenzoate (2) with a series of primary and acyclic secondary amines. The plots of kobs vs amine concentration are linear for the reaction of 2 with primary amines. The slope of the Bronsted-type plot for the reaction of 2 with primary amines decreases from 0.77 to 0.17 as the amine basicity increases, indicating that the reaction proceeds through a zwitterionic addition intermediate in which the rate-determining step changes from the breakdown of the intermediate to the reaction products to the formation of the intermediate as the amine basicity increases. On the other hand, for reactions with all the acyclic secondary amines studied, the plot of kobs vs amine concentration exhibits an upward curvature, suggesting that the reaction proceeds through two intermediates, e.g., a zwitterionic addition intermediate and an anionic intermediate. The microscopic rate constants (k1, k-1, k2, and k3 where available) have been determined for the reactions of 2 with all the primary and secondary amines studied. The k1 value is larger for the reaction with the primary amine than for the reaction with the isobasic acyclic secondary amines, while the k-1 value is much larger for the latter reaction than for the former reaction. The k3 value for the reaction with secondary amine is independent of the amine basicity. The small k2/k-1 ratio is proposed to be responsible for the deprotonation process observed in aminolyses of carbonyl or thiocarbonyl derivatives.
- Um, Ik-Hwan,Lee, Seung-Eun,Kwon, Hey-Jin
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p. 8999 - 9005
(2007/10/03)
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- Enthalpies of combustion of thiobenzamide, N,N-dimethylthiobenzamide, and N,N-diethylthiobenzamide
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The standard (p0 = 0.1 MPa) molar enthalpies of combustion in oxygen at 298.15 K of crystalline thiobenzamide, N,N-dimethylthiobenzamide, and N,N-diethylthiobenzamide to produce CO2(g), N2(g), and H2SO4*115H2O(l) were measured by rotating-bomb calorimetry.The standard molar enthalpies of sublimation at 298.15 K were measured by microcalorimetry. These results form the basis of a bond-energy scheme to estimate ΔfH0m(C6H5CSNR2, g).
- Silva, Maria D. M. C. Ribeiro da,Souza, Pilar,Pilcher, Geoffrey
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p. 173 - 178
(2007/10/02)
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- X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 20. DECARBOXYLATION OF α-IMINO ACIDS. MECHANIZM AND APPLICATIONS TO THIOAMIDE SYNTHESIS
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α-Imino acids, prepared from α-keto acids and primary amines, undergo facile decarboxylation to the corresponding imines on heating at =80 deg C in benzene or methylene chloride.Decarboxylation proceeds via a 1,2-ylide which can be trapped by sulphur to give the corresponding secondary thioamides in good yield. 1,2-Ylides from secondary amines and α-keto acids can be generated in situ and trapped with sulphur to give tertiary thioamides in excellent yield.
- Aly, Moustafa F.,Grigg, Ronald
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p. 7271 - 7282
(2007/10/02)
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