A green method synthesis and antimicrobial activity of 2-amino-4H-chromene derivatives

Article abstract of DOI:10.14233/ajchem.2018.21191

Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Trad

Full text of DOI:10.14233/ajchem.2018.21191

Asian Journal of Chemistry; Vol. 30, No. 7 (2018), 1496-1502
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2018.21191
A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives
*
K. KANTHARAJU and SANTOSH Y. KHATAVI
Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University,Vidyasangama, NH-4, Belagavi-
5
91 156, India
*Corresponding author: E-mail: kk@rcub.ac.in
Received: 21 December 2017;
Accepted: 22 April 2018;
Published online: 31 May 2018;
AJC-18920
Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived
media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Traditionally, these
reactions were performed in organic solvents and used expensive catalysts with elevated temperature. These catalytic media showed
distinct properties during reaction course such as, in situ base, homogeneous catalysts and reducing agent. The present work reviewed
green protocol synthesis of 2-amino-4H-chromene derivatives employing reaction of substituted benzaldehyde, malononitrile and α/β-
naphthol or resorcinol; three component reaction catalyzed in the presence of water extract of banana peel ash (WEB) extraction under
microwave and grindstone methods is described. The reaction found eco-friendly, simple reaction condition with easy separation of final
product in pure form. The final product was characterized for its homogeneity using spectroscopic techniques. Some of the selected
chromene derivatives (3b, 3d, 3g) prepared in this method is tested for its in vitro antimicrobial studies. The bioassay revealed that
products 3b and 3d showed positive response and comparable antimicrobial activity with the reference compounds.
Keywords: Chromene, Green method, Water extract of banana peels, Microwave irradiation, Antimicrobial activity.
cher to discover novel and competitive methodologies for the
synthesis, where the derivative can be synthesized one pot with
an environmentally friendly protocol are of recent interest of
synthetic chemists [10-13]. Multicomponent reactions have
been employed successfully to generate highly diversified combi-
natorial libraries for high through put screening of biomole-
cules [14,15]. This type of reaction was highly important in
medicinal chemistry because it allows highly complex poly
functional molecule through one-pot simple and one step reaction
[16]. Multicomponent reactions with environmentally benign
solvents and catalytic synthesis are one of the suitable green
protocols, which meet the requirements of green aspects of
developing library of biomolecules by organic synthesis [17].
Organic reaction carried out in water has become highly popular
in recent trends due to its specific medicating organic reactions
and it's environmentally friendly [18]. Several procedures for
the synthesis of chromene derivatives through multicomponent
reactions are reported [19]. Chromenes are generally synthe-
sized through three component reaction of phenol/naphthol,
aromatic aldehyde and malononitrile in the presence of catalyst
[20,21].A vast variety of catalyst have been reported by several
authors such as HTMAB [22], DABCO [23,24], p-TSA [10,25],
CTA-Cl [26], [bimim]-OH [27], thiourea oxide, TBA-Br [28],
INTRODUCTION
Green chemistry in the past two decades playing important
environmental impact, and continuous effort to come up with
an alternative methodology that minimizes use of the hazardous
solvents during chemical synthesis and reduction of reaction
time [1]. Therefore in the recent year's use of agro-waste stuff
ash extract as a chemical surrogates becomes one of the most
exciting discoveries of organic chemists [2]. Many authors
reported a novel route for the Suzuki-Miyaura cross-coupling
reactions using water extract of banana peel ash (WEB) as
solvent system as well as in situ base for the reaction [3-5]. It
2−
3
is also well documented that burnt ash contains K, Na, CO
−
and Cl as a major constituents along with a trace elements
like Ca, Mg and Cu [6]. It is believed that presence of carbonates
of Na and K of banana peel ash extract act as a base and prom-
otes reactions in the faster rate with microwave irradiation.
Thus, the feasibility of using inherent basicity of water extract
of banana peel ash in this reaction required serious consideration.
In medicinal chemistry, 2-amino-4H-chromene derivative scaffolds
plays an important role with wide range of biological applica-
tions, such as anticancer, antiallergic, antiproliferative, antiviral,
antibacterial and apoptosis inducers [7-9]. Such wide range
of biological applications of chromene derivatives made resear-
MgO nanoparticles [29], STA [30], CuSO
4
·5H O [31], ammo-
2

Vol. 30, No. 7 (2018)
nium acetate [32], Et
A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives 1497
1647.56 (C=C), 1449.69, 1408.18, 1313.09, 1249.82, 1053,
3
N [33], K
2
CO
3
[34], Fe(HSO
4
) [35] and
3
1
piperidine [36]. Most of these traditional reported methods
required purification steps, long reaction time and use of volatile
organic solvents with elevated temperatures [26,37]. Micro-
wave accelerated organic reactions have been received great
importance, due to their simplicity in operations, elimination
of the solvents and reduction of the reaction time resulting high
yield with purity compare to conventional heating [20,38,39].
The application of microwave accelerated has been employed
in various useful transformations involving condition, oxid-
ation [40-43], reduction [44], protection-deprotection [45-49],
rearrangement reactions synthesis of different heterocyclic
scaffolds [50].As part of our research interested on green method
synthesis of biologically active heterocyclic scaffolds, we present
one pot product formation of 2-amino-4H-chromene in water
extract of banana peel ash [3,4]. The synthesis is influenced
in the presence of microwave accelerated and grindstone method.
H NMR (DMSO-d
6.82 (m, 3H), 7.18 (m, 3H), 7.26 (t, 2H), 9.6 (s, 1H); C NMR
(DMSO-d 400 MHz): 102.12, 112.32, 113.70, 120.57, 126.56,
6
400 MHz,δ ppm): 4.62 (s,1H), 6.47 (t, 2H),
13
6
127.31, 129.83, 146.30, 148.81, 157.02, 160.19. HR-MS theore-
+
tical [M] 264, observed m/z 265.01. Elemental analysis of
C
16
H
12
N
2
O
2
Calc. (found) %: C 72.72 (72.64), H 4.58 (4.59),
N 10.60 (10.58) and O 12.11 (12.13).
Compound 3f: m.p. 186-188 ºC, IR (KBr, νmax, cm ):
3421.33 and 3360.02 (NH ), 3310.02 (C-H), 2190.11 (C=N),
1592.11 (C=C), 1588.12, 1499.54, 1488.35, 1445.34, 1187.11.
-1
2
1
H NMR (DMSO-d
6
400 MHz, δ ppm): 2.22 (s, 3 H), 4.34 (s,
1H), 6.02 (d, 1H), 6.41 (d, 1H), 6.59 (d, 1H), 6.79 (brs, 2H),
13
7.33 (d, 1H), 7.45 (d, 1H); C NMR (DMSO-d
13.98, 44.39, 101.28, 112.32, 120.19, 121.85, 122.56, 120.72,
29.93, 142.11, 142.28, 142.55, 160.01, 160.97. HR-MS theor-
6
, 400 MHz):
1
+
etical [M] 278.00, observed m/z 278.45. Elemental analysis
Calc. (found) %: C 73.37 (73.38), H 5.07 (4.09),
N 10.07 (10.01) and O 11.50 (11.44).
Compound 3j: m.p.194-196 ºC, IR (KBr, νmax, cm ):
467.23 and 3339.56 (NH ), 3126.33 (C-H), 2189.45 (C=N),
499.24, 1478.22, 1230.22, 1168.45. H NMR (DMSO-d
of C17
H
14
N
2
O
2
EXPERIMENTAL
-
1
All the reagents used in the synthesis were purchased from
Sd-fine Chemicals and were used without further purification.
The melting points were determined by the open capillary tube
method and are uncorrected.The water extract of banana peel
ash (WEB) solution is subjected to elemental analysis by the
ESICO Microprocessor flame photometry model 1382. FT-IR
spectra were measured with Thermo Fischer scientific using
3
1
2
1
6
400
MHz): 3.98 (s, 3H), 4.22 (s, 3H), 4.40 (s, 1H), 5.34 (s, 2H), 7.45-
1
3
7
1
1
.85 (m, 9H); C NMR (DMSO-d , 400 MHz): 15.89, 44.48,
6
11.22, 113.29, 119.22, 123.56, 126.93, 129.68, 130.34, 142.76,
42.2, 145.22, 158.89,164.56. HR-MS theoretical [M] 358,
+
observed m/z 358.22. Elemental analysis of C22
found) %: C 73.32 (73.29), H 5.59 (5.55), N 7.77 (8.01) and
O 13.32 (13.36).
Compound 3n: m.p. 238-240 ºC, IR (KBr, νmax, cm ):
260.01 and 3440.34 (NH ), 3123.89 (C-H), 2197.32 (C=N)
640.11, 1496.90 (C=C), 1491.23, 1402.13, 1229.23, 1154.09,
H
18
N
2
O Calc.
3
1
13
KBr pellet method, H-, C-NMR spectra were obtained in
DMSO-d onAgilent spectrometer at 400 MHz. The chemical
(
6
shifts are reported in ppm (δ) relative to tetramethylsilane as
internal standard. The mass spectra are recorded in Waters
Synapt G2, USA.
Preparation of water extract of banana peel ash (WEB):
The WEB extraction is done by reported procedure using
banana peels collected from local area (Musa acuminata) [3,5]
-1
3
1
1
7
2
1
051.33, H NMR (DMSO-d
.76 (d, 1H), 7.53 (m, 3H), 7.49 (m, 2H), 7.29 (m, 3H), 7.04
6
400 MHz, δ ppm): 8.34 (d, 1H),
13
(
s, 2H), 4.75 (s, 1H); C NMR (DMSO-d6, 400 MHz): 41.22,
51.86, 112.34, 120.34, 121.67, 123.54, 124.31, 125.05, 126.87,
27.22, 128.33, 128.66, 131.90, 139.25, 144.53, 150.83, 160.23.
General procedure for the synthesis of 2-amino-4H-chromenes
Method 1: In a clean mortar the corresponding aldehyde
1
+
HR-MS theoretical [M] 376, observed m/z 376.61. Elemental
analysis of C20 OBr Calc. (found) %: C 63.34 (63.30), H
.99 (3.98), N 7.39 (7.38), O 4.22 (4.21) and Br 21.07 (21.02).
(
2 mmol), malononitrile (2 mmol), resorcinol/ α-naphthol or
H
13
N
2
β-naphthol and 3 mL of WEB solution taken. The mixture
ground for 15-25 min, the progress of the reaction was moni-
tored by TLC. After completion of the reaction, added 5 mL of
distilled water and filtered, the residue is washed with excesses
amount of distilled water followed by cold methanol. The crude
product was recrystallized by alcohol and characterized by
3
-1
Compound 3o: m.p. 224-226 ºC, IR (KBr, νmax, cm ):
350.25 and 3289.98 (NH ), 3034.62 (C-H), 2189.54 (C=N),
495.33, 1498.22, (C=C), 1521.20, 1323.11, 1241.44, 1129.02,
3
1
1
2
1
112.33, H NMR (DMSO-d , 400 MHz, δ ppm): 8.23 (d, 1H),
6
1
13
7.54 (t, 2H), 7.80 (m, 3H), 7.43 (d, 2H), 7.23 (d, 2H), 6.89 (d,
FT-IR, H-, C NMR using DMSO-d solvent and HR-MS.
6
13
1
4
1
1
3
H), 6.77 (s, 2H), 4.79 (s, 1H), C NMR (DMSO-d , 400 MHz):
6
Method 2: In a clean round bottomed flask, the correspon-
ding aldehyde (2 mmol), malononitrile (2 mmol), resorcinol/
α-naphthol or β-naphthol and 3 mL of WEB solution taken,
the mixture is subjected to microwave irradiation at 300 W
power for 3 min and the progress of the reaction was monitored
by TLC. After completion of the reaction, added 5 mL of
distilled water and filtered, the residue is washed with excesses
amount of distilled water followed by cold methanol. The crude
product was recrystallized by alcohol and characterized by
3.34, 122.66, 122.82, 125.41, 126.98, 128.92, 129.34, 130.43,
30.91, 132.23, 132.44, 133.56, 134.02, 134.98, 137.54, 145.67,
+
47.22, 162.21. HR-MS theoretical [M] 315, observed m/z
15.67. Elemental analysis of C20
H
13
2
N OF Calc. (found) %:
C 75.46 (75.51), H 4.75 (4.73), N 8.80 (8.84), O 5.03 (4.98)
and F 5.97 (5.86).
-1
Compound 3p: m.p. 241-243 ºC, IR (KBr, νmax, cm ):
389.01, 3334.40 (NH ), 3116.24 (C-H), 2178.33 (C=N),
1589.06, 1469.98 (C=C), 1434.22, 1367.56, 1256.67, 1198.45,
3
2
1
13
FT-IR, H-, C-NMR in DMSO-d
Spectral data of selected compounds
Compound 3a: m.p. 232-234 ºC, IR (KBr, νmax, cm ):
497.61 (-OH), 3428.98 (NH ), 2928.67 (C-H), 2192.28 (C=N),
6
solvent and mass by HR-MS.
1
1
089.21, H NMR (DMSO-d
6
400 MHz, δ ppm): 3.34 (s, 3H),
13
3.65 (s, 3H), 5.30 (s, 3H), 7.00 (s, 2H), 7.22-7.76 (m, 9H); C
-1
NMR (DMSO-d , 400 MHz): 42.14, 121.26, 124.42, 124.81,
6
3
2
125.73, 127.89, 128.99, 130.22, 131.41, 131.68, 132.92, 133.32,

1
498 Kantharaju et al.
Asian J. Chem.
1
33.52, 134.78, 137.44, 138.23, 146.08, 162.44. HR-MS theor-
synthesis of chromene as well as other bioactive molecule
synthesis [5,51]. Firstly, we started with the optimization of
green catalyst for the model reaction compound 3a, initial with
zero to the 5 mL with interval of 1 mL and found the minimum
amount required 3 mL of WEB solution, gave best yield even
after increase the volume. Therefore in the present work, we
have used 3 mL of WEB for all our reactions. Surprisingly,
the product formation not observed without WEB, this result
revealed the importance ofWEB media required for the reaction.
Thus, reaction of three reactants in equimolar concentration
in the presence of 3 mL ofWEB at room temperature in grinding
method about 15-25 min resulted the separation of solid product
(Scheme-I). The reaction found to be simple and not required
organic solvent for the reaction as well for the extraction.After
reaction, the mixture is diluted with water, filtered and washed
with cold methanol and water (1:1) resulted spectroscopically
pure product 3a. Further the reaction is also extended under
microwave irradiation at 300 W power with same equivalent
reactants catalyzed by WEB solution, unexpectedly found the
separation of product after 3 min irradiation. These product
separated was found to be pure enough to do direct characteri-
zation without further purification. The homogeneity of the
+
etical [M] 358, observed 359.44. Elemental analysis of C22
Calc. (found) %: C 73.32 (73.22), H 5.59 (5.48), N 7.77 (7.68)
and O 13.32 (13.24).
H
18
N
2
O
3
RESULTS AND DISCUSSION
Herein, we wish to report green protocol efficient synthesis
of 2-amino-4H-chromene derivatives (3a-p) catalyzed WEB
under the influence of both microwave irradiation and grind-
stone methods. Konwar et al. [3] have reported the extraction
of WEB from agro-waste of banana peels-ash and we adopted
the same procedure for the extraction [3], but here we selected
banana peels from local available with different variety (Musa
acuminata). Musa species are grown in 135 countries primarily
for the fruit and to a lesser extent to make fiber, banana wine
and banana beer. Here we also analyzed the composition of
ourWEB using Microprocessor flame photometry model-1382,
experimental data showed the presence of Li (55.2ppm), Na
(15.4 ppm) and K (116.25 ppm). This study shows the presence
of higher concentration of K, it is comparable with reported
data. Surprisingly, our local variety WEB solution application
explored in the cyclocondensation of three component reaction
for chromene synthesis.The authors also developed and employed
other greener reagents derived from agro-waste ash for the
1
13
product 3a was confirmed by FT-IR, H-, C-NMR and mass
spectrometry.The mechanism of the reaction is well documented
OH
CN
NH
2
CHO
X
X
OH
NC
NH2
CN
WEB
or
O
or
CN
+
+
M.W
O
CN
X
X
OH
HO
O
NH
2
OH
3(a-g)
3(m-p)
3(h-l)
X = -H, -F, -Cl, -Br, -NO , -CH , -OCH
3
2
3
Scheme-I: General synthesis of 2-amino-4H-chromene
TABLE-1
PRODUCTS, YIELDS AND PHYSICAL CONSTANTS OF DIFFERENT ALDEHYDES, MALONONITRILE AND PHENOLS
S. No.
Aldehyde
Phenol
Product
Time (min)
Yield (%)
m.p. (°C)
C H
Resorcinol
6
5
1
CN
2.5
78
232-234
(1)
(2)
HO
O
NH2
(3a)
Br
2
4-Br-C H
Resorcinol
CN
3.0
75
240-242
6
4
HO
O
NH2
(3b)

Vol. 30, No. 7 (2018)
A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives 1499
O2N
3
4
5
2-NO -C H
4
Resorcinol
Resorcinol
Resorcinol
CN
2.6
2.4
2.6
68
72
79
178-180
148-150
194-196
2
6
HO
HO
HO
O
NH2
(
3c)
F
4-F-C H
CN
6
4
O
NH2
(3d)
Cl
4-Cl-C H
CN
6
4
O
NH2
(3e)
CH3
6
3-CH -C H
Resorcinol
2.7
75
186-188
3
6
4
CN
HO
O
NH2
(3f)
C H
7
α-Naphthaldehyde)
10
7
Resorcinol
CN
2.2
74
223-225
(
HO
O
NH2
(3g)
O
NH2
β-Naphthol
8
C H
3.0
73
281-283
6
5
(
4)
CN
(3h)
MeO
9
3-OMe-C H
β-Naphthol
3.1
79
252-254
6
4
O
NC
NH2
(3i)

1
500 Kantharaju et al.
Asian J. Chem.
OCH3
H3CO
10
2,3-OMe-C H3
β-Naphthol
4.0
73
194-196
6
O
NC
NH2
(3j)
Br
11
3-Br-C H4
β-Naphthol
2.8
74
242-244
6
NC
O
H2N
(3k)
F
12
4-F-C H4
β-Naphthol
2.7
72
228-230
6
O
NC
NH2
(3l)
α-Naphthol
5)
13
C H5
2.6
76
174-176
6
(
CN
O
NH2
(
3m)
Br
14
4-Br-C H4
α-Naphthol
2.9
75
238-240
6
O
CN
NH2
(3n)
F
15
4-F-C H4
α-Naphthol
2.9
74
224-226
6
O
CN
NH2
(3o)
OCH3
OCH3
16
3,4-OMe-C H3
α-Naphthol
2.4
76
241-243
6
O
CN
NH2
(3p)

Vol. 30, No. 7 (2018)
A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives 1501
TABLE-2
ANTIMICROBIAL ACTIVITIES OF SELECTED COMPOUNDS
Zone of inhibition (mm)
Compounds
7
5 µg
13
15
12
–
50 µg
10
13
10
–
25 µg
R
12
R
10 µg
R
R
R
30
R
10
R
32
10
R
5 µg
R
R
R
–
R
R
R
–
R
R
R
–
3b
3d
3g
Klebsiella
E. coli
Ciprofloxacin
–
3
3
3
b
d
g
20
25
20
–
18
23
18
–
15
20
10
–
Ciprofloxacin
3
3
3
b
d
g
25
28
10
–
27
28
23
–
20
25
08
–
25
25
20
–
18
20
R
26
20
24
18
24
A. niger
Candida
R
–
Fluconazole
3b
3d
3g
R
20
R
R
18
R
–
Fluconazole
–
in the literature for the reaction of benzaldehyde, malononitrile
to give Knoevenagel product, subsequent Michael addition of
resorcinol or α/β-naphthol to aldol product gives intermediate
followed by cyclization of intermediate to give imine afford
final product [38]. After optimizing the reaction conditions,
different substituted aldehydes were examined, the feasibility
of this product formation whose results are tabulated in Table-1.
Further, resorcinol or α/β-naphthols reaction with malononitrile
and substituted aldehyde resulted 2-amino-4H-chromenes deri-
vative with excellent product separation under the present method.
Thus, this green protocol provides an easy method of pure product
synthesis without using further chromatographic techniques.
Biological activity: in vitro Antimicrobial activity [52]
was carried out by disc diffusion method and selected 2-amino-
ACKNOWLEDGEMENTS
One of the authors (KK) is thankful to UGC, New Delhi,
India for the award of Major Research Project {(UGC-MRP:
F.43-181/2014 (SR)} andVision Group on Science and Techno-
logy, Government of Karnataka for SMYSR award.The authors
also acknowledge to the Department of Science and Technology
for the award of DST-FIST programme.
REFERENCES
1
2
.
.
R.S. Varma, Indian J. Chem., 45B, 2305 (2006).
M. Sarmah, A. Dewan, M. Mondal, A.J. Thakur and U. Bora, RSC Adv.,
, 28981 (2016);
https://doi.org/10.1039/C6RA00454G.
6
3. M. Konwar, A.A. Ali and D. Sarma, Tetrahedron Lett., 57, 2283 (2016);
https://doi.org/10.1016/j.tetlet.2016.04.041.
W. Rattanavichai and W. Cheng, Fish Shellfish Immunol., 39, 326 (2014);
4H-chromenes (3b, 3d, 3g) showed the activity at higher concen-
4
.
trations and are comparable with ciprofloxacin and fluconazole
as standards (Table-2). Surprisingly, fluro substituted benzal-
dehyde derivative of chromene (3d) showed a broad anti-
microbial activity as compared to compounds 3b and 3g. The
chromene derivative 3b which is also halogen substituted but
not showed activity like flurine another chromene 3g, which
is more hydrophobic not showed activity from these antimi-
crobial assay revealed that highly electronegative substituted
is showed activity compare to less electronegative and hydro-
phobic aldehyde (Table-2).
https://doi.org/10.1016/j.fsi.2014.05.031.
5. P.R. Boruah, A.A. Ali, B. Saikia and D. Sarma, Green Chem., 17, 1442
2015);
(
https://doi.org/10.1039/C4GC02522A.
I.O. Olabanji, E.A. Oluyemi and O.S.Ajayi, Afr. J. Biotechnol., 11, 16512
6
.
(
2012).
7. S. Laskar, G. Brahmachari, J. Org. Biomol. Chem., 2, 1 (2014).
8
9
.
.
K. Görlitzer, A. Dehne and E. Engler, Arch. Pharm., 316, 264 (1983);
https://doi.org/10.1002/ardp.19833160315.
M. Brunavs, C. P. Dell, P. T. Gallagher, W. M. Owton and C. W. Smith,
Eur. Pat. Appl. EP, 557075 A1 19930825 (1993).
10. M. Kidwai, S. Saxena, M.K. Rahman Khan and S.S. Thukral, Bioorg. Med.
Chem. Lett., 15, 4295 (2005);
Conclusion
https://doi.org/10.1016/j.bmcl.2005.06.041.
1. D. Kumar, V.B. Reddy, S. Sharad, U. Dube and S. Kapur, Eur. J. Med.
Chem., 44, 3805 (2009);
https://doi.org/10.1016/j.ejmech.2009.04.017.
2. K.R. Desale, K.P. Nandre and S.L. Patil, Org. Commun., 5, 179 (2012).
3. V.A. Osyanin, D.V. Osipov andY.N. Klimochkin, Tetrahedron, 68, 5612
1
In the present work, agro-waste stuff ash extracted from
banana peels (WEB) as a green catalyst for the synthesis of 2-
amino-4H-chromene derivatives is reported. For the synthesis
employed substituted benzaldehyde, malononitrile and resor-
cinol or α/β-naphthol forms under microwave irradiation and
grindstone methods. The method offers simple, clean, efficient
and economic technique for the synthesis of bioactive scaffold
chromenes through green chemistry. Further selected chro-
menes derivative tested in vitro antibacterial and antimicrobial
assay in disc-diffusion method and found compounds 3b, 3d,
1
1
(
2012);
https://doi.org/10.1016/j.tet.2012.04.065.
4. R.E. Dolle, J. Comb. Chem., 5, 693 (2003);
https://doi.org/10.1021/cc0340224.
5. B. Ugi, B. Werner and A. Dömling, Molecules, 8, 53 (2003);
https://doi.org/10.3390/80100053.
1
1
16. S.V. Goswami, S.S. Pendalwar and S.R. Bhusare, Chem. Biol. Interact.,
, 171 (2016).
6
1
7. N.V. Shitole, K.F. Shelke, S.A. Sadaphal, B.B. Shingate and M.S. Shingare,
3g) are active at higher concentration and comparable with
Green Chem. Lett. Rev., 3, 83 (2010);
https://doi.org/10.1080/17518250903567246.
standard.

1
502 Kantharaju et al.
Asian J. Chem.
1
8. Y. Abrouki, A. Anouzla, H. Loukili, A. Chakir, M. Idrissi, A. Abrouki,
A. Rayadh, M. Zahouily, K.E. Kacemi, J. Bessiere, B. Marouf and S. Sebti,
Am. J. Biol. Chem. Pharm. Sci., 1, 28 (2013).
36. O. Rosati, M. Curini, M.C. Marcotullio, G. Oball-Mond, C. Pelucchini
and A. Procopio, Synthesis, 239 (2010);
https://doi.org/10.1055/s-0029-1217128.
1
9. L. Dammak, M. Kammoun, N. Allouche, H. Ammar and S. Abid, Org.
Commun., 10, 32 (2017);
37. S. Gholipour, A. Davoodnia and M. Nakhaei-Moghaddam, Adv. Studies
in Biol., 7, 423 (2015);
https://doi.org/10.25135/acg.oc.6.16.11.442.
https://doi.org/10.12988/asb.2015.51042.
2
2
2
0. A. Pourkazemi and A. Zare, Org. Chem. Res., 2, 88 (2016);
https://doi.org/10.22036/org.chem..2016.13582.
1. V.V. Throat, S.A. Dake, M.V. Katariya and R.P. Pawar, Der Chem. Sin.,
38. V.P. Pagore, S.U. Tekale and B.D. Rupnar, J. Chem. Pharm. Res., 7, 1057
(2015).
39. N.K. Shah, N.M. Shah, M.P. Patel and R.G. Patel, J. Chem. Sci., 125,
525 (2013);
https://doi.org/10.1007/s12039-013-0421-y.
40. R.S. Varma, Pure Appl. Chem., 73, 193 (2001);
https://doi.org/10.1351/pac200173010193.
6
, 37 (2015).
2. T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang and T.S. Li, Synlett, 5, 871
2004);
(
https://doi.org/10.1055/s-2004-820025.
2
3. S. Jain, P.K. Paliwal, G.N. Babu and A. Bhatewara, J. Saudi Chem. Soc.,
41. T.X.T. Luu, P. Christensen, F. Duus and T.N. Le, Synth. Commun., 38,
2011 (2008);
1
8, 535 (2014);
https://doi.org/10.1016/j.jscs.2011.10.023.
4. S. Yaragorla and P.L. Saini, Indian J. Chem., 55B, 983 (2016).
5. M.V. Reddy, G.C. Reddy and Y.T. Jeong, Tetrahedron Lett., 56, 1289
https://doi.org/10.1080/00397910801997819.
42. R.S. Varma, K.P. Naicker and P.J. Liesen, Tetrahedron Lett., 39, 8437
(1998);
2
2
(
2016);
https://doi.org/10.1016/S0040-4039(98)01922-4.
43. M.K. Mohammadi, Open J. Synth. Theory Appl., 2, 87 (2013);
https://doi.org/10.4236/ojsta.2013.23011.
44. E. Parquet and Q. Lin, J. Chem. Educ., 74, 1225 (1997);
https://doi.org/10.1021/ed074p1225.
https://doi.org/10.1016/j.tetlet.2016.02.032.
2
2
6. R. Ballini, G. Bosica, M.L. Conforti, R. Maggi, A. Mazzacani, P. Righi
and G. Sartori, Tetrahedron, 57, 1395 (2001);
https://doi.org/10.1016/S0040-4020(00)01121-2.
7. K. Gong, H.L. Wang, D. Fang and Z.L. Liu, Catal. Commun., 9, 650
45. A. Walia, S. Kang and R.B. Silverman, J. Org. Chem., 78, 10931 (2013);
https://doi.org/10.1021/jo401778e.
(
2008);
https://doi.org/10.1016/j.catcom.2007.07.010.
8. J.M. Khurana and S. Kumar, Tetrahedron Lett., 50, 4125 (2009);
https://doi.org/10.1016/j.tetlet.2009.04.125.
9. A.M. Rad and M. Mokhtary, Int. Nano Lett., 5, 109 (2015);
https://doi.org/10.1007/s40089-015-0145-8.
46. V.H. Jadhav, H.B. Borate and R.D. Wakharkar, Indian J. Chem., 45B,
322 (2006).
47. I. Saxena, N. Deka, J.C. Sarma and S. Tsuboi, Synth. Commun., 33, 4185
(2003);
2
2
3
3
3
https://doi.org/10.1081/SCC-120026335.
0. M. Farahi, B. Karami, S. Alipour and L.T. Moghadam, Acta Chim. Slov.,
48. M. Bessieres, V. Roy and L.A. Agrofoglio, RSC Adv., 4, 59747 (2014);
https://doi.org/10.1039/C4RA13033B.
49. K. Selvakumar, K.A. Prasath Lingam and R.V. Luxmi Varma, RSC Adv.,
4, 36538 (2014);
https://doi.org/10.1039/C4RA06841F.
50. M.B. Gawande, S.N. Shelke, R. Zboril and R.S. Varma, Acc. Chem. Res.,
47, 1338 (2014);
6
1, 94 (2014).
1. F.K. Behbahani and S. Maryam, J. Korean Chem. Soc., 57, 357 (2013);
https://doi.org/10.5012/jkcs.2013.57.3.357.
2. S. Kanakaraju, B. Prasanna, S. Basavoju and G.V.P. Chandramouli,
Arab. J. Chem., 10, S2705 (2017);
https://doi.org/10.1016/j.arabjc.2013.10.014.
3
3
3
3. M. Costa, F. Areias, L. Abrunhosa, A. Venâncio and F. Proença, J. Org.
Chem., 73, 1954 (2008);
https://doi.org/10.1021/jo702552f.
4. R. Heydari, R. Rahimi, M. Kangani, A. Yazdani-Elah-Abadi and M.
Lashkari, Acta Chem. IASI, 25, 163 (2017);
https://doi.org/10.1515/achi-2017-0013.
5. H. Eshghi, S. Damavandi and G.H. Zohuri, Synth. React. Inorg. Met.-
Org. Nano-Met. Chem., 41, 1067 (2011);
https://doi.org/10.1021/ar400309b.
51. G. Brahmachari, K. Nurjamal, I. Karmakar, S. Begam, N. Nayek and B.
Mandal, ACS Sustain. Chem. Eng., 5, 9494 (2017);
https://doi.org/10.1021/acssuschemeng.7b02696.
52. H.D. Isenberg, Clinical Microbiology Procedures Handbook,American
Society For Microbiology: Washington, D.C, vol. 1 (1992).
https://doi.org/10.1080/15533174.2011.591347.