179104-61-1Relevant articles and documents
Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles
Massaro, Nicholas P.,Chatterji, Aayushi,Sharma, Indrajeet
, p. 13676 - 13685 (2019)
Ketenimines are versatile synthetic intermediates capable of performing novel transformations in organic synthesis. They are normally generated in situ due to their inherent instability and high level of reactivity. Herein, we report pyridine-stabilized ketenimine zwitterionic salts, which are prepared through click chemistry from readily accessible alkynes and sulfonyl azides. To demonstrate their synonymous reactivity to ketenimines, these salts have been utilized in a cascade sequence to access highly functionalized quinolines including the core structures of an antiprotozoal agent and the potent topoisomerase inhibitor Tas-103.
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.
Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange
Sapountzis, Ioannis,Dube, Henry,Lewis, Robert,Gommermann, Nina,Knochel, Paul
, p. 2445 - 2454 (2007/10/03)
(Chemical Equation Presented) Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40°C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.