21883-27-2Relevant articles and documents
Expedient synthesis of α-(2-azaheteroaryl) acetates via the addition of silyl ketene acetals to azine- N -oxides
Londregan, Allyn T.,Burford, Kristen,Conn, Edward L.,Hesp, Kevin D.
supporting information, p. 3336 - 3339 (2014/07/08)
A new and expedient synthesis of α-(2-azaheteroaryl) acetates is presented. The reaction proceeds rapidly under mild conditions via the addition of silyl ketene acetals to azine-N-oxides in the presence of the phosphonium salt PyBroP. This procedure affords diverse α-(2-azaheteroaryl) acetates which are highly desirable components/building blocks in molecules of pharmaceutical interest but are traditionally challenging to synthesize via contemporary methods. The reaction optimization and mechanism as well as a novel electronically enhanced PyBroP derivative are described.
