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

Chia Wai Li, Tzu Hsuan Shen, Tzenge Lien Shih*

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

7 Scopus citations

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.

Original languageEnglish
Pages (from-to)4644-4652
Number of pages9
JournalTetrahedron
Volume73
Issue number31
DOIs
StatePublished - 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

  • Azachalcone
  • Chalcone
  • Claisen-Schmidt condensation
  • Michael reactionxretro-aldol reaction
  • Tandem reaction

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