80393-37-9Relevant academic research and scientific papers
The BF3·OEt2-assisted conversion of nitriles into thioamides with Lawesson's reagent
Nagl, Michael,Panuschka, Claudia,Barta, Andrea,Schmid, Walther
experimental part, p. 4012 - 4018 (2009/05/27)
A method for the thiolysis of nitriles by applying Lawesson's reagent and facilitated by the addition of boron trifluoride-diethyl ether complex is reported. The method opens an easy access to primary thioamides. Aromatic, benzylic, and aliphatic nitriles were converted into the corresponding thioamides in high to quantitative yields (even in unfavorable cases, e.g., ortho-substitut-ed benzonitriles). The reaction was performed in 1,2-dimethoxyethane-tetrahydrofuran or toluene-diethyl ether solvent mixtures at 20-50°C, and exhibited considerable selectivity in the case of multifunctional nitrile substrates, such as cyanomethyl N-acetylphenylalaninate, benzoylacetonitrile, 4-cyanobenzamide, 4-acetylbenzonitrile, or pent-3-enenitrile. Georg Thieme Verlag Stuttgart.
Syntheses of N-substituted thymine thioacetamides. A novel approach to site selective acylation of diaminoalkanes
Spycha?a, Jaros?aw
, p. 7981 - 7986 (2007/10/03)
A new series of N-substituted thiocarbamoyl derivatives containing histamine, tryptamine, and other moieties having at least one amino group attached to an aliphatic chain, has been synthesized from (1-thyminyl)thioacetamide in good isolated yields (69-86%). N-[2-(4-Imidazolyl)ethyl](1-thyminyl)thioacetamide was hydrolyzed to its amide on prolonged heating in water. Ammonium sulfide (20-22% solution in water) has found interesting new applications in the efficient synthesis of N-[2-(3-indolyl)ethyl](1-thyminyl)thioacetamide and site selective acylation of diaminoalkanes, starting directly from nitriles. (C) 2000 Elsevier Science Ltd.
