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An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes

Rana Chatterjee 1
Rana Chatterjee
, 
Anindita Mukherjee 2
Anindita Mukherjee
, 
Sougata Santra 2
Sougata Santra
, 
Grigory Vasil'evich Zyryanov 2, 3
Grigory Vasil'evich Zyryanov
, 
Oleg Nikolaevich Chupakhin 2, 3
Oleg Nikolaevich Chupakhin
, 
Adinath Majee 1
Adinath Majee
10.1016/j.mencom.2021.01.039
Published 2020-12-30
Communication , Volume 31, Issue 1, 123-124
5
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Chatterjee R. et al. An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes // Mendeleev Communications. 2020. Vol. 31. No. 1. pp. 123-124.
GOST all authors (up to 50) Copy
Chatterjee R., Mukherjee A., Santra S., Zyryanov G. V., Chupakhin O. N., Majee A. An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes // Mendeleev Communications. 2020. Vol. 31. No. 1. pp. 123-124.
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TY - JOUR
DO - 10.1016/j.mencom.2021.01.039
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.039
TI - An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes
T2 - Mendeleev Communications
AU - Chatterjee, Rana
AU - Mukherjee, Anindita
AU - Santra, Sougata
AU - Zyryanov, Grigory Vasil'evich
AU - Chupakhin, Oleg Nikolaevich
AU - Majee, Adinath
PY - 2020
DA - 2020/12/30
PB - Mendeleev Communications
SP - 123-124
IS - 1
VL - 31
ER -
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@article{2020_Chatterjee,
author = {Rana Chatterjee and Anindita Mukherjee and Sougata Santra and Grigory Vasil'evich Zyryanov and Oleg Nikolaevich Chupakhin and Adinath Majee},
title = {An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes},
journal = {Mendeleev Communications},
year = {2020},
volume = {31},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.039},
number = {1},
pages = {123--124},
doi = {10.1016/j.mencom.2021.01.039}
}
MLA
Cite this
MLA Copy
Chatterjee, Rana, et al. “An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes.” Mendeleev Communications, vol. 31, no. 1, Dec. 2020, pp. 123-124. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.039.

Keywords

p-toluenesulfonic acid
4-hydroxycoumarin
benzylation
solvent-free
styrene

Abstract

An efficient straightforward solvent-free C(3)-benzylation of 4-hydroxycoumarin with styrenes is performed by heating the reactants in the presence of p-toluenesulfonic acid. By this procedure, benzylated 4-hydroxycoumarin derivatives which exhibit various biological activities were obtained.

References

2.
Coumarin heterocyclic derivatives: chemical synthesis and biological activity
Medina F.G., Marrero J.G., Macías-Alonso M., González M.C., Córdova-Guerrero I., Teissier García A.G., Osegueda-Robles S.
Natural Product Reports, 2015
3.
10.1016/j.mencom.2021.01.039_bib0015
Athanasellis
Synthesis, 2004
4.
Recent progress in the development of coumarin derivatives as potent anti‐HIV agents
Yu D., Suzuki M., Xie L., Morris-Natschke S.L., Lee K.
Medicinal Research Reviews, 2003
5.
New synthesis and anti-HIV and antiviral properties of 3-arylsulfonyl derivatives of 4-ydroxycoumarin and 4-hydroxyquinolone
Kirkiacharian B.S., De Clercq E., Kurkjian R., Pannecouque C.
Pharmaceutical Chemistry Journal, 2008
6.
Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin
Chohan Z.H., Shaikh A.U., Rauf A., Supuran C.T.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
7.
Intestinal Anti-inflammatory Activity of Coumarin and 4-Hydroxycoumarin in the Trinitrobenzenesulphonic Acid Model of Rat Colitis
Luchini A.C., Rodrigues-Orsi P., Cestari S.H., Seito L.N., Witaicenis A., Pellizzon C.H., Di Stasi L.C.
Biological and Pharmaceutical Bulletin, 2008
8.
10.1016/j.mencom.2021.01.039_bib0040
Chiarino
Eur. Pat. Appl., 1988
9.
Long-Chain 3-Acyl-4-hydroxycoumarins: Structure and Antibacterial Activity
Cravotto G., Tagliapietra S., Cappello R., Palmisano G., Curini M., Boccalini M.
Archiv der Pharmazie, 2006
10.
Antitrypanosomal and antioxidant properties of 4-hydroxycoumarins derivatives
Pérez-Cruz F., Serra S., Delogu G., Lapier M., Maya J.D., Olea-Azar C., Santana L., Uriarte E.
Bioorganic and Medicinal Chemistry Letters, 2012
11.
Recent advances and therapeutic journey of coumarins: current status and perspectives
Barot K.P., Jain S.V., Kremer L., Singh S., Ghate M.D.
Medicinal Chemistry Research, 2015
12.
Pharmacogenomics of 4-Hydroxycoumarin Anticoagulants
Au N., Rettie A.E.
Drug Metabolism Reviews, 2008
14.
Fatykhov R.F., Savchuk M.I., Starnovskaya E.S., Bobkina M.V., Kopchuk D.S., Nosova E.V., Zyryanov G.V., Khalymbadzha I.A., Chupakhin O.N., Charushin V.N., Kartsev V.G.
Mendeleev Communications, 2019
20.
A General and Efficient Iron-Catalyzed Benzylation of 1,3-Dicarbonyl Compounds
Kischel J., Mertins K., Michalik D., Zapf A., Beller M.
Advanced Synthesis and Catalysis, 2007
21.
Nitrimines as Reagents for Metal-Free Formal C(sp2)-C(sp2) Cross-Coupling Reactions
Angeles-Dunham V.V., Nickerson D.M., Ray D.M., Mattson A.E.
Angewandte Chemie - International Edition, 2014