75784-90-6Relevant academic research and scientific papers
Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Junor, Glen P.,Romero, Erik A.,Chen, Xi,Jazzar, Rodolphe,Bertrand, Guy
supporting information, p. 2875 - 2878 (2019/02/13)
Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.
Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves
Varma, Rajender S.,Dahiya, Rajender
, p. 6293 - 6298 (2007/10/03)
A solvent-flee reductive amination of carbonyl compounds by wet montmorillonite K 10 clay supported sodium borohydride is described; microwave irradiation facilitates the procedure.
Base-initiated oxidation of alkylindeneanilines by oxygen
Grigoryan, G. S.,Tovmasyan, V. S.,Malkhasyan, A. Ts.,Martirosyan, G. T.,Beletskaya, I. P.
, p. 50 - 56 (2007/10/02)
Oxidation and alkylation processes compete in the oxidative transformation of alkylindeneanilines in an alkaline medium.Oxidation leads mainly to the formation of formanilide anbd the corresponding carbonyl compound.Alkylation leads to a product which easily eliminates the aniline molecule with the formation of a derivative of the 1-aza-1,3-diene.A combination of alkylation and oxidation led to derivatives of quinoline.It is assumed that the alkylation-dehydrocyclization-elimination of alkylindeneanilines to quinolines by the action of oxygen and alkali is a variant of the Doebner-Miller reaction.During oxidation in the presence of sodium borohydride the products from conjugate oxidation-reductiono, i.e., the α-imino and β-amino alcohols, are also formed in addition to quinolines and oxidation and alkylation products.
