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Expedient synthesis of alpha-(2-azaheteroaryl) acetates via the addition of silyl ketene acetals to azine- N -oxides
A new and expedient synthesis of alpha-(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 alpha-(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.
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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem