24889-92-7Relevant academic research and scientific papers
Heterocycle Syntheses with Anionic N-Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions
Freese, Tyll,Lücke, Ana-Luiza,Namyslo, Jan C.,Nieger, Martin,Schmidt, Andreas
, p. 1646 - 1654 (2018/04/24)
Sydnone imines were deprotonated at the C4 position to give lithium-stabilized anions, which proved to be stable for several months in solution. These anions are elements of the intersection of the substance classes of N-heterocyclic carbenes and mesomeric betaines. They can be formulated as anionic N-heterocyclic carbenes. The negative charge translates into high-field shifts of the 13C NMR resonance frequencies of C4 in comparison to other NHCs. Similar to the chemistry of N-heterocyclic carbenes, reactions with isocyanates and isothiocyanates gave 4-(N-carbamoyl)-benzoylsydnone imines in trapping reactions. As a result of ring transformations involving the characteristic π-architecture of the mesoionic framework, imidazolidine-2,4-dithiones, imidazolin-2,4-diones and 1,2,4-triazol-5-ones were formed depending on the substitution pattern of the starting materials and the reaction conditions.
Preparation method for alpha-cyanoamine
-
Paragraph 0090; 0091, (2016/10/07)
The invention discloses a preparation method for alpha-cyanoamine. According to the method, the product alpha-cyanoamine is prepared through nucleophilic substitution in a mixed solvent in the presence of an oxidizing agent with an amine compound and cyanoacetic acid as reactants, iodide as a catalyst and sodium acetate as alkali. The catalyst used in the method has high reactivity; reaction conditions are mild; the application scope of a substrate is wide; post-treatment is convenient; the yield of the target product is high; preparation process is simple, green and environment-friendly; and used raw materials are widely available.
Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids
Wang, Hongxiang,Shao, Ying,Zheng, Hao,Wang, Hanghang,Cheng, Jiang,Wan, Xiaobing
supporting information, p. 18333 - 18337 (2015/12/24)
Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α-aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination-decarboxylation of cyanoacetic acid in this transformation.
Design, synthesis and glutathione peroxidase-like properties of ovothiol-derived diselenides
Bailly, Fabrice,Azaroual, Nathalie,Bernier, Jean-Luc
, p. 4623 - 4630 (2007/10/03)
Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione.
