106718-57-4Relevant academic research and scientific papers
Intramolecular Fe(II)-Catalyzed N-O or N-N bond formation from aryl azides
Stokes, Benjamin J.,Vogel, Carl V.,Urnezis, Linda K.,Pan, Minjie,Driver, Tom G.
supporting information; experimental part, p. 2884 - 2887 (2010/08/21)
(Figure presented) Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
2,2-Disubstituted-1,2-dihydro-3H-indol-3-ones by Base- and Thermal-induced Cyclisations of o-Azidophenyl s-Alkyl Ketones and o-Azidobenzoyl Esters
Azadi-Ardakani, Manouchehr,Alkhader, Mohamed A.,Lippiatt, John H.,Patel, Dalpat I.,Smalley, Robert K.,Higson, Susan
, p. 1107 - 1112 (2007/10/02)
o-Azidophenyl s-alkyl ketones in ethanolic potassium hydroxide at room temperature undergo loss of nitrogen and cyclisation to 2,2-dialkyl-1,2-dihydro-3H-indol-3-ones in high yield.Kinetic data (E(act.) 62.4 and 71.6 kJ mol-1, respectively) obtained for the o-azidophenylisopropyl and o-azidophenylcyclohexyl ketones support an assisted nitrogen loss from the azide via the enolate ion, rather than a nitrene reaction. 1,2-Dihydro-3H-indol-3-ones, along with in some cases 2,1-benzisoxazoles, have been obtained by the thermolysis and spray vacuum pyrolysis of other o-azidophenyl alkyl ketones, diethyl o-azidobenzoyl malonate, and ethyl o- azidobenzoyl(phenyl)acetate.
