54920-46-6Relevant academic research and scientific papers
Alternative tandem cyclisation pathways in the reaction between imines and enones
Girling, P. Ricardo,Batsanov, Andrei S.,Calow, Adam D.J.,Shen, Hong C.,Whiting, Andrew
, p. 1105 - 1113 (2016)
Dihydroisoquinoline reacts with Danishefsky's diene under Lewis acidic conditions or neat, to give low to moderate yields of the formal aza-Diels-Alder, [4+2]-cycloadduct. However, using methoxyvinyl methylketone with Lewis acid catalysis does not give the aza-Diels-Alder adduct, rather a formal [2+2+2]-cycloaddition occurs to provide access to a diacetyl dihydropyridine. Increased Lewis acid loading results in reduced dihydropyridine formation, and instead, a trimerisation reaction of the methoxyvinyl methyl ketone occurs, to give 1,3,5-triacetylbenzene from a different formal [2+2+2]-cycloaddition. The formal [4+2]-cycloaddition reaction of methoxyvinyl methylketone requires a cyclic imine in order to form the dihydropyridine because the reaction with acyclic imines produced a dihydropyridine from a formal [1+2+1+2]-cycloaddition. Evidence resulting from the isolation of reaction intermediates and in situ spectroscopic studies, shows that the reaction between 3,4-dihydroisoquinoline and methyl vinyl ketone, catalysed by oxy-philic Lewis acids, proceeds via a Mannich-Michael pathway and an imminium ion species. All reactions occur by one-pot cascade routes.
Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one
Um, Ik-Hwan,Lee, Eun-Ju,Min, Ji-Sook
, p. 9585 - 9589 (2007/10/03)
Second-order rate constants (kN) for the Michael-type reaction of 3-butyn-2-one (1) with a series of anilines in H2O have been determined spectrophotometrically. The kN values are dependent on the free aniline fraction (F
