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Updated: Dec 13, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Transition metal-free synthesis of sterically hindered allylarenes from 5-hexene-2-one
Ranjay Shaw1, Ismail Althagafi2, Amr Elagamy1
1Department of Chemistry, University of Delhi, North Campus, Delhi-110007, India. rpratap@chemistry.du.ac.in ramendrapratap@gmail.com.
Abstract:
A simple, efficient and transition metal-free strategy was established for the synthesis of highly functionalized, sterically hindered allylarenes (6, 7 & 8) by base-mediated ring transformation of 2-oxo-6-aryl-4-(methylthio/sec-amino)-2H-pyran-3-carbonitriles (3/4) with 5-hexene-2-one (5). This provides a method for the synthesis of allylarenes functionalized with different electron donating and withdrawing groups in one pot. The structures of isolated products 6c and 7a were ascertained by spectroscopic and single crystal X-ray diffraction analyses. In addition, we have performed a molecular docking study to predict the biological activity of the synthesized molecules for binding to estrogen receptor alpha (ERα) and estrogen receptor beta (ERβ).
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