145134-48-1Relevant academic research and scientific papers
Electrochemically initiated hydrocyanomethylation of N-heteroaryl-substituted azomethines
Windeck, Anne-Kathrin,Hess, Ulrich,Steckhan, Eberhard,Reck, Guenter
, p. 1471 - 1476 (2007/10/03)
The acetonitrile anion (1-), generated by electrochemical initiation and chemical regeneration, may be used as cyanomethylation reagent for C,N double bond structures, e.g. for hydrocyanomethylation of π-deficient N-heteroaryl-substituted Schiff bases (2-12) yielding the β-aminonitriles (2a-12a). The synthesis is initiated by deprotonation of acetonitrile (1) to 1- by cathodically generated azomethine radical anions (2-? - 12-?) followed by nucleophilic reaction of 1 with 2-12 up to its complete consumption, in a cyclic self-reproducing process of 1-. Besides 2a-12a, 3,4-heteroaryl-substituted 4-amino-3-butenonitriles and 1,3-heteroaryl-substituted 1,3-diaminoisobutyronitiles are formed in the course of a nearly currentless reaction. VCH Verlagsgesellschaft mbH, 1996.
Electrocatalyzed Cyanomethylation of Azomethines: A New Synthesis for β-Aminonitriles
Hess, U.,Raasch, A.-K.,Schulze, M.
, p. 487 - 490 (2007/10/02)
Certain Schiff-bases (2-7) react in acetonitrile (1) at a Hg-cathode in a new electrocatalyzed cyanomethylation method in good yields without sideproducts to β-aminonitriles (2a-7a).The synthesis is initiated by an electrochemical deprotonation of 1 by azomethine-radical anions in catalytical amount to acetonitril anions (B-).During nucleophilic reaction of B- with 2-7 up to its complete consumption, the cyanomethylation synthon B- is regenerated in a cyclic, self-reproducing process.Quantum chemical calculation in context with cyanomethylation product analysis permit mechanistical insights and exact prediction of suitable azomethines and coupling position for B-.
