154312-63-7Relevant articles and documents
Synthesis of N-cyanoalkyl-functionalized imidazolium nitrate and dicyanamide ionic liquids with a comparison of their thermal properties for energetic applications
Drab, David M.,Smiglak, Marcin,Shamshina, Julia L.,Kelley, Steven P.,Schneider, Stefan,Hawkins, Tommy W.,Rogers, Robin D.
, p. 1701 - 1717 (2011)
The synthesis of 10 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl- and N-butyl-N-((CH2)nCN)imidazolium; n = 1-4) nitrate and 11 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl-N-((CH2)nCN)imidazolium; n = 1-6, N-(2-cyanoethyl)-N-((CH2)nCN)imidazolium; n = 1,3-6) dicyanamide salts was achieved via N-alkylation of substituted imidazoles with commercially available haloalkylnitriles followed by anion exchange. Based on their observed melting points, all dicyanamide salts and all but one nitrate salt (1-cyanomethyl-3-methylimidazolium nitrate) had melting points 100 °C, as did 13 of the 17 halide precursors also reported here. Differential scanning calorimetry data indicated that melting points decreased by increasing the N-alkyl or N-cyanoalkyl chain length or by exchanging with the dicyanamide anion, which produced the lowest melting points in comparison to analogous halide or nitrate salts. Thermogravimetric analyses indicated that thermal stability increased for longer N-cyanoalkyl substituent lengths and decreased significantly for nitrates and more so for dicyanamides bearing short-chain N-cyanoalkyl substituents (e.g., N-cyanomethyl, N-(1-cyanoethyl), and N-(2-cyanoethyl)) in comparison to halide precursors. Furthermore, for many of the N-cyanoalkyl-substituted salts (especially the dicyanamides), there was a significant production of thermally-stable char - presumably due to by-products formed from the reaction of either N-cyanoalkyl substituents, dicyanamide anion, or both, which resulted in thermally-stable polymers or cycles.
Domino reaction of N-(cyanomethyl)-1,3-azolium quaternary salts with o-hydroxybenzaldehydes: Scope and limitations
Voskressensky,Festa,Storozhenko,Le,Nguyen,Varlamov
, p. 12442 - 12445 (2015)
A route towards chromenes, annulated with an imidazo[5,1-c][1,4]thiazine core through a base-promoted domino reaction of thiazolium quaternary salts, has been developed. The synthesised compounds show high cytotoxic activity against human tumour cell line
General Reductive Amination of Aldehydes and Ketones with Amines and Nitroaromatics under H2 by Recyclable Iridium Catalysts
Sui, Dejun,Mao, Fei,Fan, Haipeng,Qi, Zhengliang,Huang, Jun
supporting information, p. 1371 - 137 (2017/10/05)
Heterogeneous iridium catalysts were prepared and applied for the reductive amination of aldehydes and ketones with nitroaromatics and amines using H2. The iridium catalysts were prepared by pyrolysis of ionic liquid 1-methyl-3-cyanomethylimidazoulium chloride ([MCNI]Cl) with iridium chloride (IrCl3) in activated carbons. Iridium particles were well dispersed and stable in the N-doped carbon materials from [MCNI]Cl with activated carbon. The Ir@NC(600-2h) catalyst was found to be highly active and selective for the reductive amination of aldehydes and ketones using H2 and a variety of nitrobenzenes and amines were selectively converted into the corresponding secondary and tertiary amines. The Ir@NC(600-2h) catalyst can be reusable several times without evident deactivation.
