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3-(2-Phenyl-oxo-ethoxy)-2H-chromen-2-one as New 3-Hydroxycoumarin Derivative: Synthesis, Characterization and Fragmentation Study in ESI-MS

Jules Yoda1, 2,, Siaka Sosso2, Abdoulaye Djandé2, Adama Saba2

1Department of Traditional Medicine and Pharmacopoeia-Pharmacy (MEPHATRA-Ph), Institute for Health Sciences Research (IRSS), Ouagadougou, Burkina Faso

2Laboratory of Molecular Chemistry and Materials (LCMM), Team of Organic Chemistry and Phytochemistry (ECOP), University Joseph Ki-Zerbo, Ouagadougou, Burkina Faso

World Journal of Organic Chemistry. 2020, 8(1), 11-16. DOI: 10.12691/wjoc-8-1-4
Received June 17, 2020; Revised July 18, 2020; Accepted July 28, 2020

Abstract

Coumarin derivatives are an important class of heterocyclic compounds with interesting physical and biological properties. 3-(2-phenyl-oxo-ethoxy)-2H-chromen-2-one is prepared by reacting 2-chloro-1-phenylethanone with 3-hydroxycoumarin in tetrahydrofuran using a suitable base. The structure of the newly obtained compound has been confirmed by conventional analytical methods such as infrared (IR), mass spectrometry (MS) and nuclear magnetic resonance spectrometry (NMR). In mass spectrometry, fragmentation was studied in the context of the correlation between the fragmentation process and the value of the electronic charges obtained by the semi-empirical method AM1. This method, recently introduced in the study of mass spectra, allows to improve the explanation of the fragmentation process in ESI-MS and EIMS and even to predict fragment ions. We were able to successfully synthesize the title compound. The proposed structure was elucidated by spectral analysis. Concerning the fragmentation process, a good correlation between the fragmentation pathways and the electronic charges of the atoms was obtained.

Keywords:

3-hydroxycoumarin, 3-(2-phenyl-oxo-ethoxy)-2H-chromen-2-one, AM1, electronic charges, fragmentation
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