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Lankri D, Albarghouti G, Mahameed M, et al. 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. J Org Chem. 2017;82(14):7101-7113doi: 10.1021/acs.joc.7b00516.
Lankri, D., Albarghouti, G., Mahameed, M., & Tsvelikhovsky, D. (2017). 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. The Journal of organic chemistry, 82(14), 7101-7113. https://doi.org/10.1021/acs.joc.7b00516
Lankri, David, et al. "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." The Journal of organic chemistry vol. 82,14 (2017): 7101-7113. doi: https://doi.org/10.1021/acs.joc.7b00516
Lankri D, Albarghouti G, Mahameed M, Tsvelikhovsky D. 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. J Org Chem. 2017 Jul 21;82(14):7101-7113. doi: 10.1021/acs.joc.7b00516. Epub 2017 Jun 30. PMID: 28627896.
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J Org Chem. 2017 Jul 21;82(14):7101-7113. doi: 10.1021/acs.joc.7b00516. Epub 2017 Jun 30.

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.

The Journal of organic chemistry

David Lankri, Ghassan Albarghouti, Mohamed Mahameed, Dmitry Tsvelikhovsky

Affiliations

  1. The Institute for Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem , Jerusalem 91120, Israel.

PMID: 28627896 DOI: 10.1021/acs.joc.7b00516

Abstract

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.

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