115307-43-2Relevant academic research and scientific papers
Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene
Frost, Grant B.,Mittelstaedt, Michaela N.,Douglas, Christopher J.
, p. 1727 - 1732 (2019/01/09)
Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.
Axial Chirality about Boron-Carbon Bond: Atropisomeric Azaborines
Mazzanti, Andrea,Mercanti, Elia,Mancinelli, Michele
supporting information, p. 2692 - 2695 (2016/06/15)
The preparation of atropisomeric 2,1-borazaronaphthalenes is described. Resolution of the atropisomeric pair was achieved by preparative Chiral Stationary Phase HPLC (CSP-HPLC). The absolute configuration of the stereogenic axis was derived from Time-Depe
A Convenient Synthesis of Substituted Quinolines by Thermal Electrocyclic Rearrangement of o-Vinyl Anils under Nonacidic Conditions
Qiang, Lin Guo,Baine, Neil H.
, p. 4218 - 4222 (2007/10/02)
Anils 8a-g (Table II) underwent smooth rearrangement and oxidation to the quinolines 9a-g at 155-200 deg C via formation of the 2-3 carbon-carbon bond.These cyclizations proceeded in high yields under nonacidic conditions.It was often possible to prepare
