TY - JOUR
T1 - Multifaceted α-Enaminone
T2 - Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations
AU - Lankri, David
AU - Albarghouti, Ghassan
AU - Mahameed, Mohamed
AU - Tsvelikhovsky, Dmitry
N1 - Funding Information:
This project was financially supported by Yissum Research Development Company of the Hebrew University of Jerusalem.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/7/21
Y1 - 2017/7/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85025124882&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b00516
DO - 10.1021/acs.joc.7b00516
M3 - Article
C2 - 28627896
AN - SCOPUS:85025124882
SN - 0022-3263
VL - 82
SP - 7101
EP - 7113
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -