ARTICLE
Green synthesis of bis-coumarin derivatives using Fe(SD)
3
as a catalyst and investigation of their biological activities
Nosrat O. Mahmoodi
1
| Zeinab Jalalifard
2
| Ghanbari Pirbasti Fathanbari
1
1
Department of Chemistry, Faculty of
Sciences, University of Guilan, Rasht, Iran
2
Department of Chemistry, Ghadr Institute
of Higher Education, Kuchesfahan,
Rasht, Iran
Correspondence
Nosrat O. Mahmoodi, Department of
Chemistry, Faculty of Sciences, University
of Guilan, P.O. Box 41335-1914, Rasht,
Iran.
Email: mahmoodi@guilan.ac.ir
Abstract
A convenient, practical, green, and environmentally friendly method was devel-
oped for the synthesis of biscoumarins and corresponding tetrakis products from
the reaction of 4-hydroxycoumarin and various aldehydes. The bis-coumarins were
synthesized in high yield under mild reaction conditions. Products were obtained in
the presence of in situ prepared Fe(SD)
3
[Iron(III) dodecyl sulfate] as a combined
Lewis acid–surfactant catalyst (LASC) in water in short reaction times. Also, the
antibacterial activity of compounds was screened against Pseudomonas aeruginosa
and Escherichia coli as Gram-negative bacteria and Micrococcus luteus and Staph-
ylococcus aureus as Gram-positive bacterial strains. Products 3g, 3k–l were most
active than cefotaxime against E. coli and also compounds 3c and 3g were most
active than cefotaxime against S. aureus.
KEYWORDS
4-Hydroxycoumarin, bis-coumarins, green synthesis, terephthaldehyde, tetrakis-coumarins
1 | INTRODUCTION
Coumarin derivatives are an important class of heterocyclic
compounds and their biological activities make them inter-
esting targets for multicomponent reactions (MCRs). More-
over, their biological activities involve HIV inhibitory,
[1]
antibacterial,
[2]
anticancer,
[3]
anticoagulant,
[4]
antihepatitis C
virus,
[5]
vasorelaxants,
[6]
enzymatic inhibitors,
[7]
antitumor,
[8]
and spasmolytic
[9]
activities. Also, coumarins
are used as food and cosmetic additives and as brightening
agents.
[10,11]
Synthetic routes to coumarins include
Pechmann condensation, Perkin, Knoevenagel, and
Reformatsky reactions as well as flash vacuum pyrolysis.
[12]
Among these, the Knoevenagel reaction is the most com-
monly applied one, in which different types of acid catalysts
such as H
2
SO
4
, P
2
O
5
, AlCl
3
, I
2
, and F
3
CCO
2
H are
employed.
[13,14]
Many of the reactions are undesirable for
industrial purposes due to difficult conditions, longer reac-
tion times and corrosive reagents. Therefore, finding mild
and economical synthetic methods is necessary to overcome
the previous procedures. In 2009, Sangshetti et al. reported
the use of MnCl
2
.4H
2
O for condensation of
4-hydroxycoumarin and aldehydes in H
2
O at 100
C in mod-
erate to good yields (99%).
[15]
Other procedures that used
microwaves
[16]
and ultrasound irradiation
[17]
have been car-
ried out using catalysts such as molecular I
2
,
[18]
[bmim]
[BF4],
[19]
(Bu)
4
NBr (TBAB),
[20]
sodium dodecyl sulfate
(NaOSO
2
OC
12
H
25
) (SDS),
[21]
P
4
VPy–CuO-NPs,
[22]
RuCl
3
.
nH
2
O,
[23]
sulfated titania [TiO
2
/SO
4
2-
],
[24]
Melamine
trisulfonic acid (MTSA),
[25]
tetrabutylammonium hexa-
tungstate [TBA]
2
[W
6
O
19
],
[26]
Ni-NPs,
[27]
POCl
3
in dry
dimethylformamide (DMF),
[28]
TiO
2
@KSF,
[29]
ZnO
nanocomposite,
[30]
diethyl aluminum chloride (Et
2
AlCl),
[31]
LiClO
4
,
[32]
Piperidine,
[33]
nano-Fe
3
O
4
,
[34]
kit-6-mesoporous
silica-coated magnetic nanoparticles,
[35]
amino glucose-
functionalized silica-coated NiFe
2
O
4
nanoparticles,
[36]
Fe
3
O
4
@SiO
2
@KIT-6,
[37]
[BDBDMIm]Br-CAN,
[38]
citric
acid,
[39]
and SBPDSA.
[40]
More catalysts and different
Received: 19 November 2018 Revised: 22 April 2019 Accepted: 26 May 2019
DOI: 10.1002/jccs.201800444
© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–11. http://www.jccs.wiley-vch.de 1