Issue 32, 2020

Transition metal-free synthesis of sterically hindered allylarenes from 5-hexene-2-one

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).

Graphical abstract: Transition metal-free synthesis of sterically hindered allylarenes from 5-hexene-2-one

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2020
Accepted
16 Jul 2020
First published
16 Jul 2020

Org. Biomol. Chem., 2020,18, 6276-6286

Transition metal-free synthesis of sterically hindered allylarenes from 5-hexene-2-one

R. Shaw, I. Althagafi, A. Elagamy, R. Rai, C. Shah, V. Nemaysh, H. Singh and R. Pratap, Org. Biomol. Chem., 2020, 18, 6276 DOI: 10.1039/D0OB01318H

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