150596-76-2Relevant academic research and scientific papers
Highly selective N-Alkylation of amines promoted on silica: An efficient and recyclable surface
Basu, Basudeb,Paul, Susmita,Nanda, Ashis K.
experimental part, p. 1115 - 1120 (2010/05/02)
N-Alkylation of amines suffers from competing over alkylations. At the same time, use of strong base and other harsh conditions greatly limits providing a practical, generalized and selective procedure. Activated silica gel has been found to promote N-alkylations of amines. Here, we studied N-alkylation of amines with various types of alkyl halides, which finally constitute practical, highly selective and eco-friendly conditions for mono- or bis-alkylated amines at ambient temperature with recyclability of silica.
Microwave-assisted aza-Cope rearrangement of N-allylanilines
González, Israel,Bellas, Iria,Souto, Ana,Rodríguez, Ramón,Cruces, Jacobo
, p. 2002 - 2004 (2008/09/19)
The aza-Cope rearrangement of N-allylanilines is described. The use of BF3·OEt2 and microwave irradiation allows to run the transformation under mild conditions and in reaction times of minutes.
Lewis Acid-Promoted 3-Aza-Cope Rearrangement of N-Alkyl-N-allylanilines
Beholz, Lars G.,Stille, John R.
, p. 5095 - 5100 (2007/10/02)
The 3-aza-Cope rearrangement of N-alkyl-N-alkylaniline substrates, which required 250 deg C to proceed thermally, was promoted by Lewis acid reagents at 111-140 deg C.Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent.Of the many Lewis acids investigated, ZnCl2 (140 deg C) and Et2O*BF3 (111 deg C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement.With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of rearrangement and produced moderate site selectivity on the aromatic ring.Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring.Overall, both ZnCl2 and Et2O*BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.
