7336-15-4Relevant academic research and scientific papers
Nucleophilic addition to iminium ethers in the preparation of functionalized N-alkyl heterocycles
Fenster, Erik,Smith, Brenton T.,Gracias, Vijaya,Milligan, Gregory L.,Aube, Jeffrey
, p. 201 - 205 (2008/09/16)
(Chemical Equation Presented) Bicyclic iminium ethers can be synthesized by the reactions of ketones with hydroxyalkyl azides. These cationic species react with a variety of nucleophiles via two possible pathways. The initially formed, kinetic product arises from direct addition to the iminium carbon in the substrate. In some cases, the initial adduct reverts to the starting iminium ether and the ultimate product arises from nucleophilic displacement at the O-alkyl group to afford the terminally functionalized N-substituted amide. The behavior of a range of nucleophiles was studied by using several iminium ethers. In general, the relevant pathway could be identified by characterization of the product formed. For hydroxide addition, which can afford only one product regardless of mechanism, the reaction was shown to arise by the kinetic pathway, using 18O-labeled hydroxide. A one-pot synthesis of functionalized lactams entailing treatment of ketones first with hydroxyalkyl azides followed by nucleophilic addition was also developed.
A facile synthesis of the intermediates of the bicyclic organic bases: DBU and TBD
Cheng,Liu
, p. 3191 - 3194 (2007/10/02)
Intermediates of DBU and TBD, N-(3-aminoproply) - ε -caprolactam and bis- (3-aminopropyl)-amine were prepared by the hydrogenolysis of N-(2-cyanoethyl) - ε - caprolactam and di- (β-cyanoethyl)-amine respectively over Raney-Ni in the presence of NaBH4 under atmospheric pressure with mild condition and good yield.
