Semisynthesis and DFT Study of New Michael Adducts using (E)-Α-Atlantone, Isolated from Cedrus Atlantica Essential Oil-Reference-Cited by-同舟云学术

Semisynthesis and DFT Study of New Michael Adducts using (E)-Α-Atlantone, Isolated from Cedrus Atlantica Essential Oil

Published:2024-07-15 Issue: Volume:21 Page:
ISSN:1570-1786
Container-title:Letters in Organic Chemistry
language:en
Short-container-title:LOC

Author:

Nejjari Rida¹,Bashir Maryam²,Raji Houria³,Es-Sounni Bouchra¹,Adardour Mohamed⁴,Siddique Farhan²,Bakhouch Mohamed¹,Mouzdahir Abdelkrim¹,Benharref Ahmed³,Mazoir Noureddine¹,Chtita Samir⁵

Affiliation:

1. Bioorganic Chemistry Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 24, 24000 El Jadida, Morocco

2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bahauddin Zakariya University 60800, Multan. Pakistan

3. Laboratory of Natural Substances Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, P.O. Box 2390, 40000, Marrakech, Morocco

4. Laboratory of Molecular Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, P.O. Box 2390, 40000, Marrakech, Morocco

5. Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M’Sik, Hassan II University of Casablanca, P.O. Box 7955 Casablanca, Morocco

Abstract

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.

Publisher

Bentham Science Publishers Ltd.