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

Jules Yoda; Salfo Ouédraogo; Adama Saba

doi:doi:10.11648/j.sjc.20190704.12

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

Jules Yoda, Salfo Ouédraogo, Adama Saba

Published in Science Journal of Chemistry (Volume 7, Issue 4)

Received: 20 September 2019 Accepted: 14 October 2019 Published: 23 October 2019

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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.

Published in	Science Journal of Chemistry (Volume 7, Issue 4)
DOI	10.11648/j.sjc.20190704.12
Page(s)	77-81
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Coumarins, 3-Hydroxycoumarin, Chromen-2, 3-Dione, Fluorescence Properties

References

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[4]	Symeonidis T., Chamilos M., Hadjipavlou-Litina D. J., Kallitsakis M., & Litinas K. E. Synthesis of hydroxycoumarins and hydroxybenzo [f]-or [h]coumarins as lipid peroxidation inhibitors. Bioorganic & Medicinal Chemistry Letters 2009, 19 (4): pp. 1139–1142.
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[6]	Au N., Rettie A E. Pharmacogenomics of 4-hydroxycoumarin anticoagulants. Drug Metab. Rev. 2008, 40 (2): pp. 355–375.
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[8]	Dong Y., Nakagawa-Goto K., Lai C., Morris-Natschke S., Bastow K., Lee K. Antitumor agents 278. 4-Amino-2H-benzo [h]chromen-2-one (abo) analogs as potent in vitro anticancer agents. Bioorg. Med. Chem. Lett. 2010, 20, pp. 4085–4087.
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[14]	Liang C., Jiang H., Zhou, Z., Lei D., Xue Y., Yao Q. Ultrasound-promoted greener synthesis of novel trifurcate 3-substituted-chroman-2, 4-dione derivatives and their drug-likeness evaluation. Molecules 2012, 17, pp. 14146–14158.
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APA Style

Jules Yoda, Salfo Ouédraogo, Adama Saba. (2019). 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Science Journal of Chemistry, 7(4), 77-81. https://doi.org/10.11648/j.sjc.20190704.12

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ACS Style

Jules Yoda; Salfo Ouédraogo; Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci. J. Chem. 2019, 7(4), 77-81. doi: 10.11648/j.sjc.20190704.12

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AMA Style

Jules Yoda, Salfo Ouédraogo, Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci J Chem. 2019;7(4):77-81. doi: 10.11648/j.sjc.20190704.12

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@article{10.11648/j.sjc.20190704.12,
  author = {Jules Yoda and Salfo Ouédraogo and Adama Saba},
  title = {2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties},
  journal = {Science Journal of Chemistry},
  volume = {7},
  number = {4},
  pages = {77-81},
  doi = {10.11648/j.sjc.20190704.12},
  url = {https://doi.org/10.11648/j.sjc.20190704.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20190704.12},
  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 (IF). 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.},
 year = {2019}
}

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TY - JOUR
T1 - 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties
AU - Jules Yoda
AU - Salfo Ouédraogo
AU - Adama Saba
Y1 - 2019/10/23
PY - 2019
N1 - https://doi.org/10.11648/j.sjc.20190704.12
DO - 10.11648/j.sjc.20190704.12
T2 - Science Journal of Chemistry
JF - Science Journal of Chemistry
JO - Science Journal of Chemistry
SP - 77
EP - 81
PB - Science Publishing Group
SN - 2330-099X
UR - https://doi.org/10.11648/j.sjc.20190704.12
AB - 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 (IF). 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.
VL - 7
IS - 4
ER -

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Author Information

Jules Yoda

Department of Medicine, Traditional Pharmacopeia and Pharmacy / Research Institute for Health Sciences, Ouagadougou, Burkina Faso; Laboratory of Molecular Chemistry and Materials, University Joseph KI-Zerbo, Ouagadougou, Burkina Faso
Salfo Ouédraogo

Department of Medicine, Traditional Pharmacopeia and Pharmacy / Research Institute for Health Sciences, Ouagadougou, Burkina Faso
Adama Saba

Laboratory of Molecular Chemistry and Materials, University Joseph KI-Zerbo, Ouagadougou, Burkina Faso

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Jules Yoda, Salfo Ouédraogo, Adama Saba. (2019). 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Science Journal of Chemistry, 7(4), 77-81. https://doi.org/10.11648/j.sjc.20190704.12

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ACS Style

Jules Yoda; Salfo Ouédraogo; Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci. J. Chem. 2019, 7(4), 77-81. doi: 10.11648/j.sjc.20190704.12

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AMA Style

Jules Yoda, Salfo Ouédraogo, Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci J Chem. 2019;7(4):77-81. doi: 10.11648/j.sjc.20190704.12

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@article{10.11648/j.sjc.20190704.12,
  author = {Jules Yoda and Salfo Ouédraogo and Adama Saba},
  title = {2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties},
  journal = {Science Journal of Chemistry},
  volume = {7},
  number = {4},
  pages = {77-81},
  doi = {10.11648/j.sjc.20190704.12},
  url = {https://doi.org/10.11648/j.sjc.20190704.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20190704.12},
  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 (IF). 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.},
 year = {2019}
}

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