Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C–O Bond Forming Annulations

Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C–O Bond Forming Annulations
David Lankri, Dmitry Tsvelikhovsky, Ghassan Albarghouti, Mohamed Mahameed
The new reactivity of α,β-unsaturated enaminones driven by their “dual electronic attitude” is reported. We introduce unexplored, α-enaminone synthones and reveal the unusual functionalities of these building blocks. The feasibility of this new concept is demonstrated in the direct functionalization of enaminone precursors, such as alkylation; 1,2- 1,3-, or 1,4-addition; and C–O bond formation. The general and potential applicability is presented through the collective synthesis of several important classes of heterocycles via controlled cyclizations of easily accessible common precursors. The rapid composition of novel key α-enaminone synthones yields an assembly of oxazines, azaspirones, quinolinones, and quinolinols in a regio- and chemoselective fashion.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00516

DOI: 10.1021/acs.joc.7b00516

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