2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties

Abstract

Natural or synthetic coumarins are of great interest, since many of them show prominent biological activity and photochemical characteristics. In particular, hydroxycoumarins and their derivatives have been extensively studied in various fields such as biology, medicine, physics and chemistry. Among the well-known compounds is 7-hydroxycoumarin, also known as umbelliferone and 4-hydroxycoumarin. Against 3-hydroxycoumarin and its derivatives are less known and studied. In this study, new acyl derivatives were synthesized from 3-hydroxycoumarin or chromen-2,3-dione its tautomeric form and chloride acid in the presence of an appropriated base. The structures of the newly obtained compounds were confirmed by elemental analysis, mass spectrometry (MS), IR and NMR spectrometry and X-ray diffractometry. In addition, the fluorescence properties of the titre compounds were also studied in both liquid and solid state. In liquid media, the study concerned their behaviour in fluorescence emission spectrometry in 6 solvents of different polarities. The new heterocyclic compounds have been successfully synthesized. Fluorescence spectrum analyses show that these compounds are all fluorescent in both solid and liquid state with varying fluorescence intensities (I F ). On solvatochromic analyses, it appears that the behaviour of the spectrum depends strongly on the solvent. The fluorescence intensity and wavelength (λem) vary depending on the nature of the substituent (R) and especially that of the solvent. It should also be noted that chloroform is the solvent that most enhances the fluorescence of the compounds.

Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound

“…This is the case for carboxylates of 4-hydroxycoumarin [40][41][42] and 7-hydroxycoumarin [43][44][45][46]. In the case of 3-hydroxycoumarin, the crystalline structure has been established for compounds 30b, 30c, 30d, 30e, 30g, 30j, 30h [6][7][47][48][49][50][51]. The crystallographic data are here reported for compound 30b, 30e, 30g, 30h.…”

“…Previous work has shown that phenols, particularly hydroxycoumarins and some similar compounds such as homophthalic anhydrides, are suitable for acylation reactions with different results. Indeed, in the case of homophthalic anhydride, there is only C-acylation, where as in the case of hydroxycoumarin derivatives, acylation could be either O-acylation or C-acylation [6][7]32]. Several acylation processes for compound 1 have been described.…”

“…Hydroxycoumarins natural or synthetic are of great interest, since many of them show prominent biological activity and photochemical characteristics. Hydroxycoumarins and their derivatives have been extensively examined in various fields like such as biology, medicine, physics and chemistry [1][2][3][4][5][6][7][8]. Specifically, 3-hydroxycoumarin 1 and their derivatives represent less known class of hydroxycoumarin compounds.…”

“…This compound ( Figure 1) which known as 3-hydroxy-2H-chromen-2-one and 3-hydroxy-2H-1-benzopyran-2-one or 3-hydroxychromen-2-one in IUPAC system. Its structure contains two tautomeric keto-enol forms [6]. Also known as 3-hydroxychromenone, this compound represent nowadays, an important precursor in the realm of organic synthesis.…”

“…Also known as 3-hydroxychromenone, this compound represent nowadays, an important precursor in the realm of organic synthesis. Compounds possessing the 3-hydroxycoumarin nucleus are recently explore for their antioxydant activity [9], fluorescence and photopropecteur properties [6][7][8]. This review is not exhaustive, the objective is to enhance the title compound, its reactivity and its applications.…”