Title:Semisynthesis and DFT Study of New Michael Adducts using
(E)-α-Atlantone, Isolated from Cedrus atlantica Essential Oil
Volume: 22
Issue: 3
Author(s): Rida Nejjari, Maryam Bashir, Houria Raji, Bouchra Es-Sounni, Mohamed Adardour, Farhan Siddique, Mohamed Bakhouch, Abdelkrim Mouzdahir, Ahmed Benharref, Noureddine Mazoir and Samir Chtita*
Affiliation:
- Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M’Sik, Hassan II University of Casablanca, P.O. Box 7955 Casablanca, Morocco
Keywords:
Semisynthesis, Cedrus atlantica, (E)-α-atlantone, Michael adducts, DFT, Mechanistic study.
Abstract: This work is devoted to the synthesis of divers Michael adducts from (E)-α-atlantone as an
α,β-unsaturated ketone isolated from Cedrus atlantica essential oil. The (E)-α-atlantone is subjected to
ethyl cyanoacetate, phenylmagnesium bromide, and ethanol to produce the corresponding 1,4-Michael
adducts in good yields. The conjugate addition of the appropriate reagents onto (E)-α-atlantone proceeds
in a regiospecific manner, closely governed by the nucleophilicity of the reagents as well as
their stereospecific blocking. The structure of the obtained Michael adducts is established using NMR
(1H & 13C) spectroscopy and elemental analysis. Likewise, the DFT method was utilized to comprehend
the molecular properties, stability, and reactivity of the investigated compounds, as well as to
explain the proposed mechanism. The computed outcomes are in good agreement with the experimental
data.
