Reinvestigation of synthesis of halo-substituted 3-phenyl-1-(2-pyridyl)-2-propen-1-ones (azachalcones). A tandem reaction for formation of penta-substituted cyclohexanols

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Title:	Reinvestigation of synthesis of halo-substituted 3-phenyl-1-(2-pyridyl)-2-propen-1-ones (azachalcones). A tandem reaction for formation of penta-substituted cyclohexanols
Authors:	Li, Chia-Wai;Shen, Tzu-Hsuan;Shih, Tzenge-Lien
Keywords:	Azachalcone;Chalcone;Claisen-Schmidt condensation;Michael reactionxretro-aldol reaction;Tandem reaction
Date:	2017-08-03
Issue Date:	2017-07-18 02:10:31 (UTC+8)
Publisher:	Pergamon Press
Abstract:	A systematic study of the synthesis of halo-substituted azachalcones was conducted. During the reaction course, we obtained not only the target azachalcones, but also penta-substituted cyclohexanols, which are seldom reported in the literatures. The formation of penta-substituted cyclohexanols was dependent on equivalents of base used and reaction time. Their formation followed a tandem reaction: Claisen-Schmidt condensation, three Michael reactions, retro-aldol reaction, and intramolecular aldol cyclization.
Relation:	Tetrahedron 73(31), p.4644–4652
DOI:	10.1016/j.tet.2017.06.033
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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