One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles

Article abstract of DOI:10.1134/S1070363217050280

A wide variety of 2-amino-4H-chromene derivatives with diverse substituents on the 4H-chromene ring were efficiently prepared via one-pot three-component reaction of an aromatic aldehyde and malononitrile with 2-hydroxynaphthalene-1,4-dione, ethyl acetoac

Full text of DOI:10.1134/S1070363217050280

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 5, pp. 1064–1072. © Pleiades Publishing, Ltd., 2017.
One-Pot Synthesis
of Some 2-Amino-4H-chromene Derivatives
Using Triethanolamine as a Novel Reusable Organocatalyst
under Solvent-Free Conditions and Its Application
in Electrosynthesis of Silver Nanoparticles1
B. Malekia*, M. Baghayeria, S. Sheikhb, S. Babaeec, and S. Farhadia
a Department of Chemistry, Hakim Sabzevari University, Sabzevar, 96179-76487 Iran
*e-mail: b.maleki@hsu.ac.ir
b Department of Chemistry, Faculty of Science, University of Birjand, Birjand, 97179-414 Iran
c Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683 Iran
Received February 16, 2017
Abstract—A wide variety of 2-amino-4H-chromene derivatives with diverse substituents on the 4H-chromene
ring were efficiently prepared via one-pot three-component reaction of an aromatic aldehyde and malononitrile
with 2-hydroxynaphthalene-1,4-dione, ethyl acetoacetate, or naphthols in the presence of triethanolamine as a
new organocatalyst under solvent-free conditions. The procedure is transition metal-free and environmentally
friendly approach to various 2-amino-4H-chromene derivatives. Its advantages include short reaction time, high
yields, low cost, and straightforward work-up. Triethanolamine is an efficient reusable catalyst. 2-Amino-4H-
benzo[g]chromenes (ABgC) were applied as novel components of electro synthesis of silver nanoparticles.
Keywords: triethanolamine, 2-amino-4H-chromenes, transition metal-free catalysis, green chemistry, electro-
synthesis
DOI: 10.1134/S1070363217050280
INTRODUCTION
materials such as metal nanoparticles (MNs) to
enhance their utility toward a target analyte [19–21].
1-Naphthylamine was used for making an efficient
ethanol chemical sensor [22]. Li and co-workers [23]
reported a flexible multi-walled carbon nanotube
(MWCNT)–polydimethylsiloxane nanocomposite for
electrochemical DNA sensors. Salimi and co-authors
[24] developed a SiC nanoparticles/amine terminated
ionic liquid for highly sensitive detection of nitrite.
Multicomponent reactions (MCRs) are used efficiently
in organic synthesis [1]. 4H-Chromene derivatives
were detected in natural compounds [2] and demon-
strate pharmacological and biological activities [3–9].
Some synthetic approaches to 2-amino-4H-chromene
derivatives via three components one-pot reactions
involved such catalysts as triethylbenzylammonium
chloride [10], DMF/AcOH [11], Et3N [12], DBU [13],
ionic liquids [14], NH4OAc [15], KF [16], urea [17],
and some others. Most of these methods suffer from
such drawbacks as complex workup procedure, high
temperature, strong acidic conditions, prolonged reac-
tions time, large amounts of catalysts involved, and
low yields.
Herein, synthesis of 2-amino-4-(phenyl)-5,10-
dihydro-5,10-dioxo-4H-benzo[g]chromene-3-carbonitrile
(2-amino-DDBC) as an efficient and stable base for
electrochemical synthesis of silver nanoparticles
(Ag NPs) on 2-amino-DDBC modified glassy carbon
electrode (2-amino-DDBC–GCE) is presented.
Electrochemical behavior of the resulting Ag NPs was
studied by cyclic voltammetry (CV). Electrocatalytic
capability of the as-prepared Ag NPs–2-amino-DDBC–
GC electrode was studied in oxidation of glucose.
Organic compounds have been offered as sensing-
base materials [18], that interact with other sensing
1 The text was submitted by the authors in English.
1064

ONE-POT SYNTHESIS OF SOME 2-AMINO-4H-CHROMENE DERIVATIVES
1065
Scheme 1.
O
OH
O
O
O
NH2
CN
3
room temperature
O
Ar
7a−7k
O
O
O
Ar
OEt
Me
CN
NH2
4
EtO
100οC
Me
O
OH
8l−8q
TEA
ArCHO+ CH2(CN)2
Solvent-free
O
NH2
CN
5
1
2
110οC
Ar
9r−9u
OH
O
NH2
CN
6
110οC
Ar
10v−10x
RESULTS AND DISCUSSION
Initially the catalytic activity of triethanolamine in
synthesis of 2-amino-4H-benzo[g]chromenes via three-
component condensation was studied. Reaction of
benzaldehyde (1 mmol) with malononitrile (1.2 mmol)
and 2-hydroxy-1,4-naphthaquinone (1 mmol) was
carried out in the presence of various amounts of
triethanolamine under different conditions (Table 1).
Application of triethanolamine (0.1 mL) as the reaction
medium led to the desired product, 2-amino-4-(phenyl)-
5,10-dihydro-5,10-dioxo-4H-benzo[g]chromene-3-
carbonitrile (7a), in 82% yield within 10 min (Table 1,
entry 7).
Highly efficient one-pot synthesis of a variety of
chromene derivatives including substituted 2-amino-
4H-benzo[g]chromenes (7a–7k), 2-amino-3-cyano-4H-
pyrans (8l–8q) and 2-amino-2-chromenes (9r–9u,
10v–10x) catalyzed by triethanolamine under solvent-
free conditions is presented. The processes completed
within 4–13 min with high yields. Triethanolamine is
used as organic additive [25, 26], as metallic com-
plexing agent [27], in synthesis of nanomaterials [28],
and chemical fixation of CO2 with epoxides [29]. In
continuation of our study of methods that involve
efficient and environmentally benign reagents and
catalysts [30–51], we determined triethanolamine to be
a recyclable base and reaction medium in three-
component synthesis of various 2-amino-4H-chromene
derivatives (Scheme 1).
Reactions of diversely substituted aromatic com-
pounds with malononitrile and 4-hydroxy-coumarin at
room temperature under solvent-free conditions in the
presence of triethanolamine (0.1 mL) gave the cor-
responding 2-amino-4H-benzo[g]chromenes (Table 2,
entries 1–12) in high yields.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1066
MALEKI et al.
Table 1. Conditions of synthesis of 2-amino-4-(phenyl)-
5,10-dihydro-5,10-dioxo-4H-benzo[g]chromene-3-carbo-
nitrile (7a)
entry 13). A series of differently substituted 2-amino-3-
cyano-4H-pyrans (8l–8q) derivatives were prepared
from various aromatic aldehydes bearing electron-
withdrawing and electron-donating groups using the
same catalyst at 1000C under solvent-free conditions
in high yields (Scheme 1, Table 2, entries 13–18).
O
CHO
OH
+ CH2(CN)2
+
Generality and versatility of the catalyst was tested
in the synthesis of 2-amino-2-chromenes (9r–9u, 10v–
10x) by one-pot condensation of aromatic aldehydes
(1 mmol) with malononitrile (1.2 mmol) and α- or β-
naphthol (1 mmol) at 1100C under solvent-free
conditions in the presence of triethanolamine (0.1 mL)
(Scheme 1). Diversely substituted aromatic aldehydes
underwent the reaction with malononitrile and α- or β-
naphthol to produce 2-amino-2-chromenes (9r–9u,
10v–10x) in high yields (Table 2, entries 19–25).
O
1
2
O
O
NH2
CN
Conditions
The plausible mechanism of formation of 2-amino-
4H-chromene derivatives is proposed in Scheme 2.
3
According to the data presented in Table 3, tri-
ethanolamine could be recovered and reused five times
without significant loss in the catalytic activity.
Time, Yield,
Entry
Catalyst
Solvent, heating
min
%
H2O,
room temperature
1
2
TEA (0.1 mL)
20
60
Electrochemical characteristics of Ag NPs–2-
amino-DDBC–GCE. Attachment of Ag NPs to 2-
amino-DDBC was performed by using amperometric
method (see Eexperimental). Cyclic voltammograms
of GCE, 2-amino-DDBC–GCE and Ag NPs–2-amino-
DDBC–GCE in phosphate buffer solution (PBS, pH =
7.0) are presented in Fig. 1. In case of Ag NPs–2-
amino-DDBC–GCE two significant oxidative and
reductive peaks are observed. A clear oxidation peak at
about +0.4 V corresponds to oxidation of Ag NPs and
metal oxide formation. The cathodic peak at –0.1 V
that appear in the return cycles is related to the
reduction of silver oxides [31]. The surface coverage
(Γ) was calculated by integration of the anodic peak
charge, Q, in CV by using the equation of Γ = Q/nFA,
where n is the number of electron transferred, F is
Faraday constant, A is the surface area of the electrode.
Upon the background correction, Γ was calculated to
be 1.23×10–7 mol/cm2.
TEA (0.1 mL) H2O, reflux
7
79
EtOH,
room temperature
3
4
5
6
7
8
9
TEA (0.1 mL)
15
5
80
80
60
70
82
83
84
TEA (0.1 mL) EtOH, reflux
MeOH,
room temperature
TEA (0.1 mL)
20
10
10
TEA (0.1 mL) MeOH, reflux
Solvent-free,
TEA (0.1 mL)
room temperature
TEA (0.1 mL) Solvent-free, 35°C 10
Solvent-free,
TEA (0.15 mL)
TEA (0.05 mL)
No catalyst
10
20
60
room temperature
Solvent-free,
room temperature
10
11
80
Solvent-free,
room temperature
No
reaction
The results of SEM studies of GCE, 2-amino-DDBC–
GCE and Ag NPs–2-amino-DDBC–GCE demon-
strated that 2-amino-DDBC–GCE could be used as an
efficient supporting material for the electro-chemical
formation of Ag NPs.
The presented above protocol was extended to con-
densation of aldehydes with malononitrile and ethyl
acetoacetate. Benzaldehyde underwent three-com-
ponent condensation smoothly in the presence of
triethanolamine (0.1 mL) at 1000C under solvent-free
conditions to afford 96% of (8l) in 15 min (Table 2,
Electrocatalytic oxidation of glucose. Cyclic volt-
ammograms of glucose (0.1 mM) on the bare GCE, 2-
amino-DDBC–GCE and Ag NPs–2-amino-DDBC–
GCE in NaOH (0.1 M) (Fig. 2) demonstrated that bare
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

ONE-POT SYNTHESIS OF SOME 2-AMINO-4H-CHROMENE DERIVATIVES
1067
Table 2. One-pot synthesis of 2-amino-4H-chromene derivatives catalyzed by triethanolamine
mp, °C
calculated
Entry
Products
Ar
Time, min
Yield, %
found
262–264
247–248
252–254
270–272
254–256
238–240
254–256
1
2
3
4
5
6
7
7a
7b
7c
7d
7e
7f
C6H5
10
10
10
9
90
92
91
93
94
90
81
260–261 [14a]
248 [14a]
4-MeOC6H4
3-MeOC6H4
3,4-(MeO)2C6H3
4-Cl–C6H4
248–250 [14a]
272–273 [14a]
250 [14a]
8
2-Cl–C6H4
9
237 [14a]
7g
4-Br–C6H4
11
252–253 [14a]
8
7h
7i
4-F–C6H4
13
6
84
95
92
91
96
95
288–290
295–297
286–288
290–292
190–191
177–179
290–292 [14c]
248–250 [14a]
288 [14a]
9
3-NO2–C6H4
3,4-Cl–C6H3
2,3,4-(MeO)3C6H2
C6H5
11
12
13
14
7j
10
9
7k
8l
291–292 [14a]
190–192 [15]
177–178 [15]
15
4
8m
2-NO2–C6H4
15
16
17
18
19
20
21
22
23
24
25
8n
8o
3-NO2–C6H4
4-NO2–C6H4
2-Cl–C6H4
3-Cl–C6H4
C6H5
6
5
95
90
93
93
85
94
92
93
88
91
92
187–188
176–178
191–192
180
187–188 [15]
175–176 [15]
191–192 [15]
180–181 [15]
209–211 [16]
232 [16]
8p
8q
9r
4
10
7
209–210
230–231
238–240
212–214
118–120
187–188
280–282
9s
4-Cl–C6H4
2-Cl–C6H4
3-Cl–C6H4
4-MeOC6H4
4-NO2–C6H4
3-NO2–C6H4
4
9t
6
238–240 [16]
213–214 [16]
119–120 [16]
186 [16]
9u
10v
10w
10x
4
15
9
7
283–284 [16]
GCE (Fig. 2, curve 1) displayed no electrochemical
response in the presence of glucose, while a week
broad oxidation peak was observed for 2-amino-
DDBC–GCE (Fig. 2, curve 2) in the potential range
from 0.4 to 1.15 V. Upon addition of glucose
(0.1 mM), Ag NPs–2-amino-DDBC–GCE (Fig. 2,
curve 3) displayed a remarkable anodic current about
187 µA at 0.685 V vs the reference electrode that
confirmed the electrocatalytic activity of Ag NPs in
oxidation of glucose.
EXPERIMENTAL
Chemicals were obtained from Merck and Sigma-
Aldrich. Melting points were determined in open
capillary tubes in a Stuart BI Branstead Electrothermal
apparatus. IR spectra were recorded on a Shimadzu
1
435-U-04 spectrophotometer (KBr pellets). H NMR
spectra were measured on a Jeol FT NMR 300 MHz
spectrometer in CDCl3 or DMSO-d6 using TMS as an
internal reference. SEM images were recorded on a
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1068
MALEKI et al.
Scheme 2.
O
O
N
O
NH
CN
O
C
C
H
CN
H
O
Ar
O
Ar
Ar
O
Tautomerism
O
CN
EtO
OH
O
O
NH2
Me
O
NH2
CN
8l−8q
O
O
Tautomerism
TEA
O
Ar
Ar
O
7a−7k
H
CN
NH
O
EtO
Me
Ar
O
OH
O
O
O
OH
TEA
O
O
TEA
H
Me
EtO
EtO
Me
Ar
O
Ar
CN
CN
O
H
N
H
OH
HO
CN
EtO
H
C
O
H
OH
Me
H
N
NC
CN
TEA
NH
N
C
H
CN
O
CN
Ar
O
TEA
Tautomerism
O
NH2
CN
Ar
H
Ar
9r−9u
Hitachi S4160 instrument. Electrochemical experi-
ments including cyclic voltammetry (CV) were
recorded with a Metrohm (797 VA Computrace,
Switzerland) controlled by a personal computer. The
measurements were carried out using a conventional
three electrode cell using an Ag|AgCl|KCl (3 M)
electrode as the reference and Pt wire as the counter
(auxiliary) electrode. A glassy carbon electrode with a
geometrical area of 0.0314 cm2, bare or modified, was
used as a working electrode.
Synthesis of 2-amino-4H-benzo[g]chromenes (7a–
7k). A mixture of an aldehydes (1 mmol) with malono-
nitrile (1.2 mmol) and 2-hydroxy-1,4-naphthaquinone
(1 mmol) was stirred with triethanolamine (0.1 mL) at
room temperature for a certain period of time (Table 2)
(for solid aldehydes 5–10 drops of ethanol were
added). Upon completion of the reaction as indicated
by TLC (hexane: ethyl acetate, 4 : 1) hot EtOH (96%,
2 mL) was added and the mixture stirred for 2 min.
The resulting crude product was poured onto crushed
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

ONE-POT SYNTHESIS OF SOME 2-AMINO-4H-CHROMENE DERIVATIVES
I, μA
1069
I, μA
3
4
3
2
2
1
1
E, V
E, V
Fig. 2. (1) Cyclic voltammogram of AgNPs/2-amino-
DDBC/GCE in absence of glucose and cyclic
voltammograms of glucose (0.1 mM) in NaOH (0.1 M) at
the surface of different electrodes: bare (2) GCE), (3) 2-
amino-DDBC–GCE, and (3) AgNPs–2-amino-DDBC–
GCE at scan rate.
Fig. 1. Cyclic voltammogram of (1) bare GCE, (2) 2-amino-
DDBC–GCE, and (3) AgNPs–2-amino-DDBC–GCE in
0.1 M PBS (pH = 7.0) at scan rate 100 mV s–1.
ice and the solid product was filtered off and recrys-
tallized from ethanol (96%, 5 mL) to get the cor-
responding pure 2-amino-4H-benzo[g]chromene
derivative (Table 2).
the precipitated solid was recrystallized from ethanol
(96%, 5 mL) to afford pure 2-amino-2-chromene deri-
vatives (9r–9u, 10v–10x) (Table 2).
Preparation of Ag NPs–2-amino-DDBC–GCE.
The glassy carbon electrode (GCE) was polished with
alumina slurries and rinsed with distilled water in
ultrasonic bath for 3 min, rinsed with ethanol, nitric
acid, and doubly distilled water in ultrasonic bath. The
clean GCE was dried at ambient temperature prior to
modification. 2-Amino-DDBC (0.5 mg) was sonicated
in 1 mL of distilled water to obtain white suspension.
2-Amino-DDBC suspension (10 µL) was placed on the
surface of clean GCE. After being dried in the air
2-amino-DDBC functionalized GCE (2-amino-DDBC–
GCE) was immersed in 1 mM of AgNO3 solution.
Synthesis of 2-amino-3-cyano-4H-pyrans (8l–8q).
A mixture of an aldehyde (1 mmol) with malononitrile
(1.2 mmol) and ethyl acetoacetate (1 mmol) was
stirred at room temperature for 2 min, then tri-
ethanolamine (0.1 mL) was added and the mixture was
heated on an oil bath at 110°C with stirring for the
certain time (Table 2). Upon completion of the
reaction (TLC, hexane:ethyl acetate, 8 : 2), hot EtOH
(96%, 2 mL) was added and the mixture stirred for
2 min. Then the resulting reaction mixture was poured
onto crushed ice and the precipitated solid was recrys-
tallized from ethanol (96%, 5 mL) to afford the cor-
responding pure 2-amino-3-cyano-4H-pyran deriva-
tives (8l–8q) (Table 2).
Table 3. Efficiency of the recycled triethanolamine in the
synthesis of 2-amino-4H-chromene derivatives
Comp.
no.
Number of
recycle
Synthesis of 2-amino-2-chromenes (9r–9u, 10v–10x).
A mixture of an aldehyde (1 mmol) with malononitrile
(1 mmol) and α- or β-naphthol (1 mmol) was stirred at
room temperature for 2 min. Upon following addition
of triethanolamine (0.1 mL) the mixture was heated on
an oil bath at 100°C with stirring for the time indicated
in Table 2. Upon completion of the reaction (TLC,
hexane:ethyl acetate, 8 : 2), hot EtOH (96%, 2 mL)
was added to the mixture and stirred for 2 min. Then
the reaction mixture was poured onto crushed ice and
1
2
3
4
5
6
7a
Yield, %
90 90 89 86 83 80
10 10 10 10 10 10
95 93 93 90 90 86
Time, min
Yield, %
8n
Time, min
6
6
6
6
6
6
10v Yield, %
88 86 84 84 82 80
15 15 15 15 15
Time, min
15
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1070
MALEKI et al.
5. Suresh, T., Arunima, V., Atin, K., Sandeep, G.,
Prarthana, V.R., and Ganesh, R.K., Acta. Pol. Pharm.,
2010, vol. 67, p. 423.
6. Jain, N., Xu, J., Kanojia, R.M., Du, F., Jian, Z.G.,
Emmanuel, P., and Sui, Z., J. Med. Chem., 2009,
vol. 52, no. 23, p. 7544. doi 10.1021/jm900146e
Synthesis of Ag NPs was performed by the electro-
deposition on 2-amino-DDBC–GCE at 0.0 V for 120 s
in 1 mM AgNO3 solution in the atmosphere of N2.
CONCLUSIONS
7. (a) Mun, J., Jabbar, A.A., Devi, N.S., Liu, Y., Van-
Meir, E.G., and Goodman, M.M., Bioorg. Med. Chem.,
2012, vol. 20, no. 14, p. 4590. doi 10.1016/
j.bmc.2012.04.064; (b) Banskota, A.H., Tezuka, Y.,
Tran, K.Q., Saiki, I., Miwa, Y., Taga, T., and Kadota, S.,
Bioorg. Med. Chem. Lett., 1998, vol. 8, no. 24, p. 3519.
doi 10.1016/S0960-894X(98)00644-1
8. Cheng, J. F., Ishikawa, A., Ono, Y., Arrhenius, T., and
Nadzan, A., Bioorg. Med. Chem. Lett., 2003, vol. 13,
no. 21, p. 3647. doi 10.1016/j.bmcl.2003.08.025
9. Denish, C K., Hetal, K.P., and Nilesh, K.G., Asian. J.
Biochem. Pharm. Res., 2012, vol. 2, p. 126.
10. Changsheng, Y., Chenxia, Y., Tuanjie, L., and Shujiang, T.,
Chin. J. Chem., 2009, vol. 27, no. 10, p. 1989. doi
10.1002/cjoc.200990334
A novel one-pot three-component reaction that led
to the of synthesis 2-amino-4H-chromene derivatives
under solvent free conditions is developed. Advantages
of the present method include simple procedure, high
yields, short process time, easy work-up, no organic
solvents and toxic reagents involved. For the first time
one of derivatives of 2-amino-4H-chromene, 2-amino-
DDBC, was used for electrochemical synthesis of
Ag NPs. The Ag NPs–2-amino-DDBC–GCE exhibited
good electrochemical behavior with well-defined
redox peaks recorded that indicated the direct electron
transfer between the matrix layer and the underlying
electrode. The Ag NPs–2-amino-DDBC–GCE demon-
strated good catalytic ability of glucose oxidation
indicating its potential application in electrochemical
sensors.
11. Wang, X.H., Zhang, X.H., Tu, S.J., Shi, F., Zou, X.,
Yan, S., Han, Z.G., Hao, W.J., Cao, X.D., and Wu, S.S.,
J. Heterocycl. Chem., 2009, vol. 46, no. 5, p. 832. doi
10.1002/jhet.153
ACKNOWLEDGMENTS
12. (a) Shaabani, A., Ghadari, R., Ghasemi, S., Pedarpour, M.,
Rezayan, A.H., Sarvary, A., and Ng, S.W. J., Comb.
Chem., 2009, vol. 11, no. 6, p. 956. doi 10.1021/
cc900101w; (b) Magedov, I.V., Kireev, A.S., Jenkins, A.R.,
Evdokimov, N.M., Lima, D.T., Tongwa, P., Altig, J.,
Steelant, W.F.A., Slambrouck, S.V., Antipin, M.Y., and
Kornienko, A., Bioorg. Med. Chem. Lett., 2012, vol. 22,
no. 16, p. 5195. doi 10.1016/j.bmcl.2012.06.073
13. Khurana, J.M., Nand, B., and Saluja, P., Tetrahedron,
2010, vol. 66, no. 30, p. 5637. doi 10.1016/
j.tet.2010.05.082
14. (a) Shaterian, H.R. and Mohammadnia, M., J. Mol. Liq.,
2013, vol. 177, p. 353. doi 10.1016/j.molliq.2012.10.012;
(b) Yu, Y., Guo, H., and Li, X., J. Heterocycl. Chem.,
2011, vol. 48, no. 6, p. 1264. doi 10.1002/jhet.747;
(c) Khorami, F. and Shaterian, H.R., Res. Chem.
Intermed., 2015, vol. 41, no. 5, p. 3171. doi:10.1007/
s11164-013-1423-6
The authors are thankful to the Research Council of
Hakim Sabzevari University for partial support of this
work.
REFERENCES
1. (a) Veisi, H., Maleki, B., Hamelian, M., and Sedigh
Ashrafi, S., RSC Adv., 2015, vol. 5, no. 9, p. 6365;
(b) Maleki, B., Org. Prep. Proced. Int., 2015, vol. 47,
no. 2, p. 173178; (c) Maleki, B., and Taimazi, F., Org.
Prep. Proced. Int., 2014, vol. 46, no. 3, p. 252;
(d) Maleki, B., Rezaei-Seresht, E., and Ebrahimi, Z.,
Org. Prep. Proced. Int., 2015, vol. 47, no. 2, p. 149.
2. (a) Hatakeyama, S., Ochi, N., Numata, H., and Takano, S.,
J. Chem. Soc. Chem. Commun., 1988, vol. 17, p. 1202;
(b) Singh, K., Singh, J., and Singh, H., Tetrahedron,
1996, vol. 52, no. 45, p. 14273; (c) Martín, N., Martínez‐
Grau, A., Seoane, C., Marco, J.L., Albert, A., and
Cano, F.H., Lieb. Ann. Chem., 1993, vol. 7, no. 7, p. 801.
15. Shaterian, H.R. and Kangani, M., Sci. Iran., 2013,
vol. 20, no. 3, p. 571. doi 10.1016/j.scient.2012.11.019
16. Maleki, B., Babaee, S., and Tayebee, R., Appl.
Organomet. Chem., 2015, vol. 29, no. 29, p. 408. doi
10.1002/aoc.3306
3. Kidwai, M., Saxena, S., Rahman-Khan, M.K., and
Thukral, S.S., Bioorg. Med. Chem. Lett., 2005, vol. 15,
no. 19, p. 4295.
17. Brahmachari, G. and Banerjee, B., ACS Sustain. Chem.
Eng., 2014, vol. 2, no. 3, p. 411. doi 10.1021/sc400312n
18. Khan, A.T., Lal, M., Ali, S., and Khan, M.M.,
Tetrahedron Lett., 2011, vol. 52, no. 41 , p. 5327. doi
10.1016/j.tetlet.2011.08.019
4. (a) Pospisil, J. and Marko, I. E., J. Am. Chem. Soc.,
2007, vol. 129, no. 12, p. 3516. doi 10.1021/ja0691728;
(b) El-Saghier, A.M., Naili., M.B., Rammash, B.K.,
Saleh, N.A., and Kreddan, K.M., Arkivoc, 2007, vol. 16,
p. 83.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

ONE-POT SYNTHESIS OF SOME 2-AMINO-4H-CHROMENE DERIVATIVES
1071
19. Kumar, D., Reddy, V.B., Sharad, S., Dube, U., and
Kapur, S., Eur. J. Med. Chem., 2009, vol. 44, no. 9,
p. 3805. doi 10.1016/j.ejmech.2009.04.017
38. Baghayeri, M., Nazarzadeh Zare, E., and Namadchian, M.,
Sensor Actuat. B-Chem., 2013, vol. 182, p. 467. doi
10.1016/j.snb.2013.07.028
20. Moshtaghi Zonouz, A., Moghani, D., and Okhravi, S.,
39. Baghayeri, M., Nazarzadeh Zare, E., and Mansour
Lakouraj, M., Acta., 2015, vol. 182, nos. 3–4, p. 771.
doi 10.1007/s00604-014-1387-2
Current. Chem. Lett., 2014, vol. 3, no. 2, p. 71.
21. Moshtaghi Zonouz, A., Eskandari, I., and Moghani, D.,
Chem. Sci. Trans., 2012, vol. 1, no. 1, p. 91. doi
10.7598/cst2012.143
22. Sánchez, A., Hernández, F., Cruz, P.C., Alcaraz, Y.,
Tamariz, J., Delgado F., and Vázquez, M.A., J. Mex.
Chem. Soc., 2012, vol. 56, no. 2, p. 121.
40. Baghayeri, M., Nazarzadeh Zare, E., and Mansour
Lakouraj, M., Sensor. Actuat. B: Chem., 2014, vol. 202,
p. 1200. doi 10.1016/j.snb.2014.06.019
41. Baghayeri, M., Nazarzadeh Zare, E., and Mansour
Lakouraj, M., Biosens. Bioelectron., 2014, vol. 55,
p. 259. doi 10.1016/j.bios.2013.12.033
23. Bihani, M., Bora, P.P., and Bez, G., J. Chem., 2013,
p. 785930. doi 10.1155/2013/785930
42. Ameen, S., Akhtar, M.S., Umar, A., and Shin, H.S.,
Chem. Eng. J., 2013, vol. 229, p. 267. doi 10.1016/
j.cej.2013.05.112
24. Heravi, M.M., Beheshtiha, Y.S., Pirnia, Z., Sadjadi, S.,
and Adibi, M., Synth. Comm., 2009, vol. 39, no. 20,
p. 3663. doi 10.1080/00397910902796102
43. Li, J. and Lee, E.C., Biosens. Bioelectron., 2015,
25. Heravi, M.M., Zakeri, M., and Mohammadi, N., Chin. J.
Chem., 2011, vol. 29, no. 6, p. 1163. 10.1002/
cjoc.201190217
vol. 71, p. 414. doi 10.1016/j.bios.2015.04.045
44. Salimi, A., Kurd, M., Teymourian, H., and Hallaj, R.,
Sensor. Actuat. B: Chem., 2014, vol. 205, p. 136. doi
10.1016/j.snb.2014.08.035
26. Babu, N.S., Pasha, N., Rao, K.V., Prasad, P.S., and
Lingaiah, N., Tetrahedron. Lett., 2008, vol. 49, no. 17,
p. 2730. doi 10.1016/j.tetlet.2008.02.154
45. (a) Khoraamabadi-Zad, A., Azadmanesh, M., Karamian, R.,
Asadbegy, M., and Akbari, M., RSC Adv., 2014, vol. 4,
p. 47721; (b) Li, H.J. and Wang, L., Eur. J. Org. Chem.,
2006, vol. 22, p. 5099.
27. Wang, X.S., Zhou, J. X., Zeng, Z.S., Li, Y.L., Shi, D.Q.,
and Tu, S., Arkivoc, 2006, vol. 11, p. 107.
28. Rathod, S., Arbad, B., and Land, M., Chin. J. Catal.,
2010, vol. 31, no. 6, p. 631. doi 10.1016/S1872-2067
(09)60078-4
46. Sohoni, S., Sridhar, R., and Mandal, G., Powder.
Technol., 1991, vol. 67, p. 277.
47. Kirillov, A.M., Kopylovich, M.N., Kirillova, M.V.,
Haukka, M., da-Silva, M.F., and Pombeiro, A., J. Angew.
Chem. Int. Ed., 2005, vol. 44, p. 4345.
29. Li, Y., Chen, H., Shi, C., and Ji, S., J. Comb. Chem.,
2010, vol. 12, no. 2, p. 231. doi 10.1021/cc9001185
30. Heravi, M.M., Baghernejad, B., and Oskooie, H.A.,
J. Chin. Chem. Soc., 2008, vol. 55, no. 3, p. 659. doi
10.1002/jccs.200800098
48. (a) Pati, R.K., Ray, J.C., and Pramanik, P., J. Am.
Ceram. Soc., 2001, vol. 84, p. 2849; (b) Liu, Y.Q. and
Gao, L., J. Am. Ceram. Soc., 2003, vol. 86, p. 1651.
31. Mosaddegh, E. and Hassankhani, A., Ultrason.
Sonochem., 2013, vol. 20, no. 6, p. 1436. doi 10.1016/
j.ultsonch.2013.04.008
49. Xiao, B., Sun, J., Wang, J., Liu, C., and Cheng, W.,
Synth. Commun., 2013, vol. 43, p. 2985.
32. Jin, T.S., Xiao, J.C., Wang, S.J., and Li, T.S., Ultrason.
Sonochem., 2004, vol. 11, no. 6, p. 393. doi 10.1016/
j.ultsonch.2003.10.002
50. (a) Maleki, B., Hemmati, S., Sedrpoushan, A., and
Sedigh Ashrafi, S., RSC Adv., 2014, vol. 4, p. 40505;
(b) Maleki, B., and Sedigh Ashrafi, S., RSC Adv., 2014,
vol. 4, p. 42873; (c) Maleki, B., Sedigh Ashrafi, S., and
Tayebee, R., RSC Adv., 2014, vol. 4, p. 41521;
(d) Tayebee, R., Jarrahi, M., Maleki, B., Kargar Razi, M.,
Mokhtari, Z.B., and Baghbanian, S.M., RSC Adv., 2015,
vol. 5, p. 10869; (e) Tayebee, R., Jomei, M., Maleki, B.,
Kargar Razi, M., Veisi, H., and Bakherad, M., J. Mol.
Liq., 2015, vol. 206, p. 119; (f) Maleki, B., Barat Nam
Chalaki, S., Sedigh Ashrafi, S., Rezaee Seresht, E.,
Moeinpour, F., Khojastehnezhad, A., and Tayebee. R.,
Appl. Organomet. Chem., 2015, vol. 4, p. 290;
(g) Maleki, B., Akbarzadeh, E., and Babaee, S., Dyes.
Pigm., 2015, vol. 123, p. 222; (h) Maleki, B., Eshghi, H.,
Khojastehnezhad, A., Tayebee, R., Sedigh Ashrafi, S.,
Esmailian Kahoo, G., and Moeinpour, F., RSC Adv.,
2015, vol. 5, p. 64850; (i) Veisi, H., Naeimi, A.R.,
33. Behbahani, F.K. and Sadeghi, M., J. Korean. Chem.
Soc., 2013, vol. 57, no. 3, p. 357. doi 10.5012/
jkcs.2013.57.3.357
34. Dekamin, M.G., Eslami, M., and Maleki, A.,
Tetrahedron, 2013, vol. 69, no. 3, p. 1074. doi 10.1016/
j.tet.2012.11.068
35. Maleki, B. and Sheikh, S., RSC Advances., 2015, vol. 5,
no. 54 , p. 42997. doi 10.1039/C5RA04458H
36. Sabitha, G., Bhikshapathi, M., Nayak, S., Srinivas, R.,
and Yadav, J.S., J. Heterocycl. Chem., 2011, vol. 48,
no. 2, p. 267. doi 10.1002/jhet.544
37. Maleki, B. and Sheikh, S., Org. Prep. Proced. Int.,
2015, vol. 47, no. 5, p. 368. doi 10.1080/
00304948.2015.1066647
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1072
MALEKI et al.
Maleki, B., Sedigh Ashrafi, S., and Sedrpoushan, A.R.,
10.1080/00304948.2016.1127102; (n) Maleki, B., Org.
Prep. Proced. Int., 2016, vol. 48, no. 1, p. 81. doi
10.1080/00304948.2016.1127104; (o) Maleki, B.,
Sheikh, E., Rezaei Seresht, E., Eshghi, H., Sedigh
Ashrafi, S., Khojastehnezhad, A., and Veisi, H., Org.
Prep. Proced. Int., 2016, vol. 48, no. 1, p. 37. doi
10.1080/00304948.2016.1127098; (p) Maleki, B.,
Davoodi, A., Vakili Azghandi, M., Baghayeri, M.,
Akbarzadeh, E., Veisi, H., Sedigh Ashrafi, S., and Raei, M.,
New J. Chem., 2016, vol. 40, no. 2, p. 1278. doi
10.1039/C5NJ02707A
Org. Prep. Proced. Int., 2015, vol. 47, p. 309;
(j) Maleki, B., Eshghi, H., Barghamadi, M., Nasiri, N.,
Khojastehnezhad, A., Sedigh Ashrafi, S., and
Pourshiani. O., Res. Chem. Int., 2016, vol. 42, p. 3071,
doi 10.1007/s11164-015-2198-8; (k) Maleki, B.,
Mohammadi Zonoz, F., and Akhlaghi, H.A., Org. Prep.
Proced. Int., 2015, vol. 47, no. 5, p. 361. doi
10.1080/00304948.2015.1066646; (l) Maleki, B.,
Esmailian Kahoo, G., and Tayebee, R., Org. Prep.
Proced. Int., 2015, vol. 47, no. 6, p. 461. doi
10.1080/00304948.2015.1088757; (m) Maleki, B., Raei, M.,
Akbarzadeh, E., Ghasemnejad-Bosra, H., Sedrpoushan, A.R.,
Sedigh Ashrafi, S., and Nabi Dehdashti, M., Org. Prep.
Proced. Int., 2016, vol. 48, no. 1, p. 62. doi
51. Baghayeri, M., Amiri, A., and Farhadi, S., Sensor.
Actuat. B: Chem., 2016, vol. 225, p. 354. doi 10.1016/
j.snb.2015.11.003
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017