66913-75-5Relevant articles and documents
Silver-promoted regio- and stereoselective aminocyanation of alkynes for the synthesis of β-aminoacrylonitriles using N-isocyanoiminotriphenylphosphorane
Chen, Lingnan,Cao, Shanshan,Zhang, Jingping,Wang, Zikun
supporting information, p. 1678 - 1681 (2019/05/29)
The silver-promoted intermolecular aminocyanation of alkynes for the synthesis of (Z)-β-aminoacrylonitriles is reported, using N-isocyanoiminotriphenylphosphorane (NIITP) as both the nitrile and amine source. The transformation proceeds in moderate to good yields, and in a regio- and stereoselective manner, using a wide range of acetylenes.
The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)-cyanomethylamines. Part 2. Mechanism
Perosa, Alvise,Selva, Maurizio,Tundo, Pietro
, p. 1033 - 1037 (2007/10/03)
The mechanism of the rearrangement of N-(1-arylalkylidene)cyanomethylamines ArC(=NCH2CN)R 1 to the corresponding nitriles ArCH(CN)R2 (in DMF, at 150°C, with K2CO3) is described. Reaction 1 → 2 was investigated for different types of imine 1, and it was found that with a leaving group other than CN- the reaction does not proceed to yield the nitrile, whereas imines such as PhC(=NCH2CN)H, prepared starting from aldehydes rather than ketones, yield the expected phenylacetonitrile even at temperatures as low as 120°C. Evidence for the mechanism comes from a study of the reactivity of the postulated intermediates: 2-cyano-3-phenylaziridine 4c, and 2,2-diphenyl-2H-azirine 5b. The route involving aziridine 4c is ruled out, since this compound does not react at all under the investigated conditions. The 2H-azirine 5b instead, yields the corresponding diphenylacetonitrile in DMF with K2CO3, at 150°C. The transformation seems to involve an initial deprotonation, followed by an intramolecular ring closure-CN elimination step, which yields the 2H-azirine. The azirine then isomerizes to the nitrile. Additional evidence for the intermediacy of the 2H-azirine, based on 1H NMR monitoring of the reaction 1 → 2, is described. Finally, the results of a simple isotope exchange experiment provide a rationale for the previously observed scrambling of labels, and further confirm the proposed mechanism.
Reaction of Hydrogen Fluoride in Pyridine Solution with cis-Cyano-2- and cis-Amido-2-aziridines. Preparation of β-Fluoro-α-amino Acids and Esters by Means of Acidic Hydrolysis and Alcoholysis of β-Fluoro-α-Amino Nitriles and/or β-Fluoro-α-Amino Acid Amide
Ayi, Ayicoue I.,Guedj, Roger
, p. 2045 - 2051 (2007/10/02)
The addition of hydrogen fluoride generated from pyridinium poly(hydrogen fluoride) (i.e.Olah's reagent) to some cis-2-cyano- and cis-2-amido-aziridines has been examined.The reaction led to fluoroamine derivatives which upon acidic hydrolysis and alcohol
