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TRANSCRIPT
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
207
Section I
SYNTHESIS OF 5-OXO-5H-INDENO[1,2-b]PYRIDINE-3
CARBONITRILE DERIVATIVES
6. I.1 Introduction
The highly conjugated, yellow alkaloid onychine was first isolated by
De Almeida et al in 1976 from Onychopetalum amazonicum (Annonaceae) [1].
The indinopyridine moiety is like the 4-azafluorenone group of this alkaloid
onychine. The naturally occurring onychine (Fig. 6.1) is having antimicrobial
properties particularly against fungus Candida albicans.
N
CH3O
(Fig. 6.1) Onychine
The infections caused by this fungus are resistant to treatment and are
opportunistic as they infect persons of weak immune system like AIDS patients
and cancer patients undergoing chemotherapy [2]. The amphotericin-B which
has used against Candida albicancs has many side effects. Therefore the
indinopyridines can be used as alternative to amphotericin-B.
Many indinopyridines are having the different biological activities like
herbicidal, calcium antagonistic activators. They are also useful in the
treatment of the neurological disorder as adenosine A2a receptor binding active
and in the treatment of inflammation related disease as a phosphodiesterase
inhibiting [3]. It has also anticandidal activity [4]. Along with these activities
they are also show wide range of pharmaceutical activities such as
antiepileptic, antimalarial, vasodilator, anesthetic, anticonvulsant and
agricultural use such as fungicidal, pesticidal, herbicidal [5].
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
208
6. I.2 Literature Review
The 1-Methyl-4-azafluoren-9-one had been synthesized
previously by Bowdcn et al [6] was prepared again by another route a year later
by Prostakov et al [7]. There are several method are available for the synthesis
of 5H-indeno[1,2-b]pyridin-5-ones. It can be synthesise by Knoevengel
condensation reaction of 1,3-indandione and aromatic aldehyde with phenyl
acetonitrile and ammonium acetate [8]. The oxidative thermal rearrangement of
2-indanone oxime O-allyl ethers also give the 5H-indeno[1,2-b]pyridin-5-ones
[9]. By the direct cyclization of 2-aryl-3-methylpyridines followed by oxidation
gives the same product [10]. Most of these methods have serious drawbacks as
more work-up and purification process, strong acid or base condition, multistep
reactions, occurrence of side reactions and more expensive use of reagents.
These reactions require harsh conditions.
The synthesis of substituted indeno[1,2-b]pyridine are made by multi-
component reactions under microwave irradiation [11] (Scheme 6.1).
+
O
O
+ Ar-COCH3
N
Ar
IAr
O
NH4OAc/DMF
MW
1 2 3 4
Ar-CHO
(Scheme 6.1)
The another methods are the cyclization of 2-aryl-3-nicotinic acids by
the use of polyphosphoric acid [12], Pummerer reaction of imidosulfoxides
[13] (Scheme 6.2), Pd(0)-catalyzed cross-coupling reaction between
arylboronic acids and 2-halopyridines [14].
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
209
CH3
COOH
CH3
CONHCH2Ar
CH3
N
O
Ar-
O
S
Et
O
N
X
CH3
OTf
N
X
CH3
(Scheme 6.2)
Recently the synthesis of indeno[1,2-b]pyridine is made by use of
catalyst L-proline [15] (Scheme 6.3).
O
O
OHC
R1
+ + RCOCH3 + NH4OAc
NR
R1
OL proline (15 mol%)ethanol (2ml)
rt 2.5 to 4hr
(Scheme 6.3)
The another way for preparation of indeno[1,2-b]pyridine is use of ceric
ammonium nitrate (CAN) [16] (Scheme 6.4).
O
O
OHC
R1
R2
O
+ + + NH4OAc
N
O
R2
R1
CAN(10 mol%)
EtOH(5 ml)
RT (20 to 300C)
strring(3 to 5 hr.)
(Scheme 6.4)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
210
The application of such MCRs toward the synthesis of 5H-indeno[1,2-
b]pyridin-5-ones gives an important and subject in organic synthesis seeing as
these products has wide applications in preparative organic chemistry. Due to
elevated reactivity, simple procedure, exceptional efficiency, and atom-
economy, multicomponent reactions (MCRs) have gained considerable interest
[17-18] (Scheme 6.5).
O
O
+ +
NH2
N
OAr
H6P2O18O62.18H2O
AcOH,refluxAr-CHO
(Scheme 6.5)
Other general method for the synthesis of indeno[1,2-b]pyridine is
reaction of active methylene with amine and aldehyde. In next step oxidation is
carried out by chromium (VI) oxide [19] (Scheme 6.6).
O
O
R2
R a
Rb
Rc
Rd
+
R4
R2
NH2 NH
O
R1
R4
R2
R a
Rb
Rc
Rd
N
O
R1
R4
R2
R a
Rb
Rc
Rd
AcOH
CrO3,AcOH/H2O2 3
4
1
(Scheme 6.6)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
211
The modification of Hantzsch reaction is done for three component
reaction. Here oxidation is carried out with DDQ or MnO2 instead of CrO3 as
shown below [20] (Scheme 6.7).
O
O
R2
R a
Rb
Rc
Rd
+R4
R2
NH2NH
O
R1
R4
R2
R a
Rb
Rc
Rd
N
O
R1
R4
R2
R a
Rb
Rc
Rd
R2CHO
DDQ,CH2Cl22 3
4
1
NH4OHMeOH
(Scheme 6.7)
The nanocrystalline metal oxides have great significance as catalyst in
different organic reactions. Because of their coordination parts and high surface
to volume ratio they provide a larger number of active sites for reactions [21-
22]. Recent years CuO nanoparticles get interested because of their use as
semiconductor [23] along with in preparation of organic and inorganic
nanocomposites [24]. In addition, copper oxide nanoparticles cheaply
available, requires only mild reaction conditions for producing high yields in
short reaction time [25] (Scheme 6.8).
2H2O2 +N
N
NH2
O
CH3CH3
+
OH
N
N
N
O
CH3
CH3
OCuO NPs
(Scheme 6.8)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
212
The nanocrystalline copper(II) oxide-catalyzed one-pot four component
synthesis of polyhydroquinoline derivatives are synthesized under solvent-free
conditions as shown below [26] (Scheme 6.9).
CH3
CH3
O
O
+
OEt
CH3
O
O
+ +
NH4OAc
X
CHO
CuO,NPs
Solvent free (1400C)
NH
OEt
O
CH3
O
CH3
CH3
X
1 2
3 4a 5a
(Scheme 6.9)
The Cu(II)O-NPs have been used as an efficient heterogeneous catalyst
in different organic reactions as: cross-coupling reactions [27], C-acylation
reaction [28] and CO and NO oxidation reactions [29]. The CuO-NPs are also
used in the multi-component reactions [30] (Scheme 6.10).
X
CHO
+ +
CN
CN
O
OCH3
CH3
CN
NH2
O
CH3
CH3
SO4-2
/MCM 41
Ethanol, reflux
(Scheme 6.10)
6. I.3 Present Work
6. I.3.1 Synthesis of CuO Nanoparticles
The CuO-nanoparticles (NPs) were prepared by the co-precipitation
method [31]. A solution of copper acetate (1.0 gm) and acetic acid (1.0 mL) in
250 mL of distilled water was heated at 1000C. Then 0.8 gm of NaOH was
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
213
added quickly under vigorous starring. The reaction mixture being cooled to
room temperature and the obtained black powder were separated by
centrifugation. The collected precipitate then washed several times with
distilled water, ethanol and dried at 1000C for 10 hrs.
6. I.3.2 Optimization of Model Reaction
In earlier studies, to optimize the reaction conditions, reaction of 3-
nitro benzaldehyde, malanonitrile, 1,3-Indandione and ammonium acetate is
chosen as model reaction for one-pot synthesis of corresponding 5-oxo-5H-
indeno[1,2-b]pyridine-3-carbonitrile derivatives (Scheme 6.11).
N
O
NH2
N
O2N
CHO
O2N
+NC
NC+
O
O
CuO-NPs
H2O, RT, StirringNH4OAc+
(Scheme 6.11)
The reaction conditions were optimized on the basis of the solvent and
concentration of catalyst (Table 6.1). The influence of solvent was studied
when the model reaction was performing by using methanol, ethanol and water.
Increasing the amount of catalyst does not show any significant changes in the
yield and time of reaction. As the result of this experiment, the best results are
obtained when the reactions were carried out in presence of CuO-NPs (0.1
mmol, 10 mol%, 0.0079 gm) under water as solvent at room temperature. The
significant result of are related to the reactivity of catalytic nanoparticles which
is largely determined by the energy of surface atoms that can be easily gauges
with the number of neighboring atoms by the bonding modes and
accompanying energies of small molecules to be transformed on the
nanoparticles surface.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
214
(Table 6.1) The optimization of model reaction by using various solvents and
concentrations of catalyst a
Entry Catalyst (mol %) Solvent Time (min) Yield (%)b
1 CuO-NPs (10) Methanol 50 65
2 CuO-NPs (10) Ethanol 65 60
3 CuO-NPs (10) Water 30 83
4 CuO-NPs (20) Methanol 50 68
5 CuO-NPs (20) Ethanol 60 65
6 CuO-NPs (20) Water 30 84
a Reaction conditions: 3-nitro benzaldehyde (1mmol), malanonitrile (1mmol), 1,3-Indandione
(1mmol) and ammonium acetate (1.5 mmol).
b Isolated yieldd.
In order to establish optimum ratio of reactants the model reaction is
carried out several times in the presence of CuO nanoparticles. The best results
were obtained when 3-nitro benzaldehyde, malanonitrile, 1,3-Indandione and
ammonium acetate were employed as substrates in a 1:1:1:1.5 ratio. To study
the scope of this process, we next utilize variety of aldehydes to investigate
four-component reactions under optimal conditions (Scheme 6.11).
6. I.3.3 Reusability of CuO nanoparticles catalyst
Finely, we were interested in studying the reusability of the catalyst due
to economic and environmental aspect. For this purpose, the reaction of 3-nitro
benzaldehyde, malanonitrile, 1,3-Indandione and ammonium acetate was
chosen as the model reaction in presence of CuO nanoparticles. At the end of
each turn, catalyst was recovered from the reaction mixture by dilution of the
mixture with chloroform, simple filtration and drying at 1000C. The catalyst
was reused several times without significant loss of its activity (Table 6.2).
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
215
(Table 6.2) Reusability of the CuO nanoparticles
Run Yield of 6A (%) Catalyst recovery (%)
1 83 97
2 80 94
3 78 91
4 75 90
6. I.3.4 General Procedure for Synthesis of 5-Oxo-5H-Indeno[1,2-
b]Pyridine -3-Carbonitrile Derivatives
The one-pot three-component condensation reactions is done in distilled
water (5 ml) with 3-nitro benzaldehyde 1 (1 mmol, 0.151 gm) and
malanonitrile 2 (1.1 mmol, 0.072 gm) in presence of CuO-NPs (0.1 mmol, 10
mol%, 0.0079 gm) is stirred at room temperature for 15 minutes and addition
of 1,3-Indandione (1 mmol, 0.146 gm) 3 was done in presence of ammonium
acetate (1.5 mmol, 0.115 gm) 4, reaction is proceeded spontaneously at room
temperature (Scheme 6.12).
The completion of the reaction is monitored on TLC. Then reaction
mixture was dissolved in chloroform. The catalyst was insoluble in CHCl3 and
separated. The solvent was evaporated and desired solid material obtained was
filtered and washed with distilled water and dried. The solid obtained was
recrystalized with chloroform:ethanol mixture (1:2) to afford the pure 5-oxo-
5H-indeno[1,2-b]pyridine -3-carbonitrile derivatives.
(Scheme 6.12)
+NC
NC DW, RT, StiringNH4OAc
O
OCHO
R
1 2 3N
O
NH2
NC
R
CuO-NPs
6 A-T4
+ +
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
216
The plausible mechanism for this reaction is shown in below (Scheme
6.13). In the first step Knoevengel condensation reaction occurs between
aldehyde1 and malanonitrile 2. In the second step 1,3-indandione 3 reacts with
the Knoevengel product by Michael addition reaction to form intermediate 4.
After addition of NH4OAc oxygen is replaced by nitrogen, which on
cyclization forms product 6. In the last step oxidation occurs followed by 1,4,
elimination of water molecule giving final product 5-Oxo-5H-Indeno[1,2-
b]Pyridine -3-Carbonitrile.
OH
R
R
CN
N
NH
O
NC
R
NH2
O
O
NC
R
NH
H
O
O
H
CN
CN
-
Knoevengel
Michael Addition
Cyclization
Cu2+
..
NH4OAc
N
O
NC
R
NH2
Oxidation
1
2
3
6
4
7
reaction
O
NH2
NC
R
NH
Cu2+
..
5
(Scheme 6.13)
The physical and analytical data for synthesis of desired 5-oxo-5H-
indeno[1,2-b]pyridine-3-carbonitrile derivatives are shown below (Table 6.3).
(Table 6.3) The physical and analytical data of 5-Oxo-5H-Indeno[1,2-b]
Pyridine-3-Carbonitrile derivatives.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
217
Sr.
No. Entry Aldehyde (R) Structure
Time
(min.)
Yield
(%)
M. P.
(0C)
1 6A 3-O2NC6H4
N
O
NH2
O2N
N
30 83 234
2 6B 4-O2NC6H4
N
O
NH2
N
NO2
30 91 130
3 6C 4-FC6H4
N
O
NH2
N
F
24 78 125
4 6D 4-ClC6H4
N
O
NH2
N
Cl
25 85 125
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
218
5 6E 4-BrC6H4
N
O
NH2
N
Br
30 87 115
6 6F 2-ClC6H4
N
O
NH2
N
Cl
40 76 95
7 6G 3-ClC6H4
N
O
NH2
N
Cl
35 89 95
8 6H 2,4-ClC6H4
N
O
NH2
Cl
N
Cl
40 70 130
9 6I 4-HOC6H4
N
O
NH2
OH
N
30 74 185
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
219
10 6J 2-HOC6H4
N
O
NH2
N
OH
35 72 115
11 6K 3-HOC6H4
N
O
NH2
N
OH
35 68 110
12 6L 3,4-HOC6H4
N
O
NH2
OH
OH
N
40 79 225
13 6M 4-H3CC6H4
N
O
NH2
CH3
N
35 94 117
14 6N 2-SC4H3
S
N
O
NH2
N
30 86 150
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
220
15 6O 4-H3COC6H4
N
O
NH2
N
OCH3
30 91 125
16 6P 3-H3COC6H4
N
O
NH2
OCH3
N
35 86 140
17 6Q 3,4-(H3CO)2C6H3
N
O
NH2
O
OCH3
CH3
N
40 73 190
18 6R 2,3,4-
(H3CO)3C6H2
N
O
NH2
N
OCH3
O
CH3
OCH3
40 78 105
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
221
19 6S C10H7
N
O
NH2
N
35 79 155
20 6T C14H9
N
O
NH2
N
40 76 105
The compounds (6A to 6T) are confirmed by spectroscopic technique
like IR, 1H NMR, 13C NMR. The data obtained is in good agreement with the
proposed structure, which confirms formation of desired compounds.
6. I.4 Experimental
The melting points are uncorrected and were determined in an open
capillary. Infrared spectra (in KBr pellets) were measured with on
spectrophotometer of a Perkin Elmer Spectrum 100. The 1H and 13C NMR
spectra were recorded on a Bruker Spectrospin Avance II-300 MHz
spectrophotometer using DMSO-d6 solvents and tetramethylsilane as an
internal standard. Chemical shifts are given in the delta scale (ppm). Mass
spectra were analyzed on a Shimadzu QP 2010 GCM. The 1,3-Indandione was
purchased from Alfa Aesar chemicals. The purity of the compounds was
checked by using TLC Silica gel 60-F254 plates. The XRD was done on X-ray
Powder Diffractometer of Bruker AXS Analytical Instruments Pvt. Ltd.
Germany Model: D2 PHASER. The SEM analysis was done using Scanning
Electron Microscope of JEOL-JSM-6360, Germany.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
222
6. I.5 Result and Discussion
The structures of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile
derivatives were confirmed from IR, 1H NMR, 13C NMR and Mass
spectrometry data. The IR spectrum of compound (6I) (Fig. 6.7) was showed
the broad peak at 3350 cm-1 is for hydroxyl group of aldehyde, peaks of
primary amine group at 3080 cm-1, for nitrile group it shoes peak at 2226 cm-1
for carbonyl ketone group it shows peak at 1722 cm-1. It also shows peak for
(C=N) group at 1666 cm-1 and for (C-N) it shows peak at 1256 cm-1 resembling
the formation of desired derivative.
The 1H NMR of same compound (6I) (Fig. 6.8) showed the phenolic
broad proton of at 10.59 δ (ppm). It exhibited the signal of amine group (-NH2)
proton attached to aromatic ring at 8.43-8.41 δ (ppm), along with peak for
aromatic protons at aromatic region of 7.86-7.68 δ (ppm) suggest the formation
of desired multi-component product. Similarly the 1H NMR of Also the
compound (6Q) (Fig. 6.23) shows multiplet peaks for two methoxy group
attached to aromatic (-OCH3) of aldehyde at 3.91-3.88 δ (ppm). Similarly the 13C NMR spectra are given all the corresponding carbons for carbonyl group
and aromatic carbon presents in the structure.
Finally, the structure of formed compound (6I) (Fig. 6.10), (6L) (Fig.
6.13), (6N) (Fig. 6.19) and (6Q) (Fig. 6.25) was confirmed from the GCMS
analysis. Compound (6L) (Fig. 6.13) shows exact mass peak at (m/z) 329M+.
For compound (6N) (Fig. 6.19) the peak at (m/z) 287 M+ obtained due to loss
of NH2 group from the compound. For the compound (6Q) (Fig. 6.25) the peak
at (m/z) 279 M+ appear due to loss of one –OCH3 and NH2 loss. Due to bulky
molecules exact mass peaks (M+) was not obtained for some compounds. The
data obtained is in good agreement with the proposed structure.
6. I.6 Conclusions
In the view of recent interest in the use of heterogeneous nanocatalysts
we have developed CuO-NPs as recyclable, easy to handle, inexpensive, non-
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
223
volatile, non-explosive and eco-friendly catalyst which can be used in many
organic transformations. The synthesis of desired 5-oxo-5H-indeno[1,2-
b]pyridine-3-carbonitrile derivatives as shown in the (Scheme 6.2), were done
by four component reaction of aldehyde with malanonitrile, 1,3-indandione and
ammonium acetate at room temperature in presence of CuO-NPs as catalyst
and water as solvent. The reusability of catalyst is also an important aspect.
The multi-component, single step, room temperature condition and water as
eco-friendly solvent give the process valuable mark. The reaction gives good
yield in short span of time.
6. I.7 Characterization of CuO Nanoparticles
The structural study of CuO nanoparticles (NPs) were done by using
powder X-ray diffraction (PXRD) (Fig. 6.2) and morphological study using
scanning electron microscope (SEM) (Fig. 6.3) respectively. The matching of
powder XRD pattern with simulated XRD pattern of crystal structure data
reported by Niggli et al [27] reveals the phase pure monoclinic structured CuO
(II) nanoparticles. The nanocrystalline nature of CuO (II) powder also clarified
by calculating the crystallite size for (111) reflection by using the Scherrer
equation (D= Kλ/βcosθ), and it is 8.04 nm. Where, K is the shape factor (0.9), λ
is the wavelength of X-rays and β is the corrected full width at half-maximum.
The SEM analysis of CuO nanoparticles carried out at different magnification
shows the agglormation nature.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
224
(Fig
. 6.2
) X
RD
Spe
ctru
m o
f CuO
Nan
opar
ticle
s,
(a)
=si
mul
ated
XR
D p
atte
rn (
b) = X
RD
pat
tern
of
the
mat
eria
l
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
225
(Fig. 6.3) Scanning Electron Microscope (SEM) images of CuO(II)NPs at
different magnification as A=500; B=2000; C=5000; D= 10,000; E= 15,000;
F=20,000 for 20kV.
A B
C D
E F
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
226
6. I.8 Spectral Data of Synthesized Compounds
2-Amino-4-(3-nitrophenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6A)
N
O
NH2
O2N
N
(Fig. 6.4)
(6A) Yellow solid; Yield=83%; M.P. = 234 0C; IR (KBr, cm-1) 3094, 3069,
2945, 1730, 1686, 1530, 1350. 1H NMR (300 MHz, DMSO d6) δ (ppm): 9.57
(s, 1H, N-H), 8.69-8.68 (d, 1H, Ar-H), 8.44-8.42 (d, 1H, Ar-H), 8.05-8.01 (m,
5H, Ar-H), 7.87-7.83 (t, 1H, Ar-H), 3.32 (s, 2H, N-H). 13C NMR (300 MHz,
DMSO d6) δ (ppm): 189.25, 188.60, 158.00, 157.00, 148.42, 143.05, 138.45,
135.96, 135.83, 134.23, 131.60, 129.75, 127.98, 127.50, 126.90, 126.76,
123.81, 123.68, MS: (m/z) 249, 165, 104, 76.
2-amino-4-(2,4-dichlorophenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6H)
N
O
NH2
Cl
N
Cl
(Fig. 6.5)
(6H) Brown solid; Yield=70%; M.P. = 130 0C; IR (KBr, cm-1) 3101, 3049,
2921, 2229, 1693, 1579, 1218. 1H NMR (300 MHz, DMSO d6) δ (ppm): 8.71-
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
227
8.69 (d, 1H, Ar-H), 8.26 (s, 1H, N-H), 8.19-8.14 (m, 1H, Ar-H), 8.05-8.00 (m,
2H, Ar-H), 7.90-7.85 (d, 2H, Ar-H), 7.52 (s, 1H, N-H), 7.45-7.38 (m, 1H, Ar-
H), 13C NMR (300 MHz, DMSO d6) δ (ppm): 197.38, 189.23, 154.52, 143.33,
142.40, 140.28, 138.95, 138.16, 135.63, 135.55, 134.47, 130.69, 130.08,
129.74, 128.32, 127.10, 123.54, 123.17, 86.01.
2-amino-4-(4-hydroxyphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6I)
N
O
NH2
OH
N
(Fig. 6.6)
(6I) Yellow solid; Yield=74%; M.P. = 185 0C; IR (Fig. 6.7) (KBr, cm-1) 3350,
3080, 2923, 2226, 1722, 1666, 1293. 1H NMR (Fig. 6.8) (300 MHz, DMSO d6)
δ (ppm): 10.59 (s, 1H, Ar-OH), 8.43-8.41(d, 2H, N-H), 7.86-7.80 (m, 7H, Ar-
H), 7.68 (d, 1H, Ar-H), 13C NMR (Fig. 6.9) (300 MHz, DMSO d6) δ (ppm):
190.39, 189.28, 163.71, 146.95, 143.36, 142.13, 139.71, 137.80, 135.71,
135.37, 135.18, 134.10, 125.40, 125.00, 122.95, 122.86, 116.87, 116.33, 45.25,
MS (Fig. 6.10):(m/z) 249, 165, 104, 76.
2-amino-4-(3,4-dihydroxyphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6L)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
228
N
O
NH2
OH
OH
N
(Fig. 6.11)
(6L) Yellow solid; Yield=79%; M.P. = 255 0C; IR (Fig. 6.12) (KBr, cm-1)
3459, 3247, 2923, 1670, 1554, 1294, MS (Fig. 6.13): (m/z) 329.30 (M+).
2-amino-4-(4-methylphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6M)
N
O
NH2
CH3
N
(Fig. 6.14)
(6M) Yellowish brown solid; Yield=94%; M.P. = 117 0C; IR (KBr, cm-1) 3036,
2922, 2223, 1686, 1557, 1189. 1H NMR (300 MHz, DMSO d6) δ (ppm): 8.41-
8.39 (d, 1H, Ar-H), 8.00-7.99 (d, 1H, Ar-H), 7.89-7.80 (d, 4H, Ar-H), 7.72 (s,
1H, N-H), 7.34-7.33 (d, 2H, Ar-H), 3.25 (s, 1H, N-H), 2.46 (s, 3H, Ar-CH3), 13C NMR (300 MHz, DMSO d6) δ (ppm): 197.41, 159.74, 147.09, 146.33,
143.33, 135.57, 135.24, 135.03, 134.45, 130.88, 130.59, 130.34, 129.62,
128.44, 123.21, 123.17, 113.97, 112.82, 81.21,21.98.
2-amino-5-oxo-4-(thiophen-2-yl)-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6N)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
229
S
N
O
NH2
N
(Fig. 6.15)
(6N) Green solid; Yield=86%; M.P. = 150 0C; IR (Fig. 6.16) (KBr, cm-1) 3065,
2921, 2224, 1688, 1585, 1206. 1H NMR (Fig. 6.17) (300 MHz, DMSO d6) δ
(ppm): 8.27 (m, 3H, N-H & Ar-H), 8.06 (s, 1H, N-H), 7.91-7.90 (m, 4H, Ar-
H), 7.38-7.31 (m, 1H, Ar-H), 13C NMR (Fig. 6.18) (300 MHz, DMSO d6) δ
(ppm): 189.49, 188.93, 153.50, 143.58, 141.41, 139.92, 138.69, 136.75, 135.90,
135.72, 135.54, 129.23, 128.93, 124.11, 122.86, 122.76, 75.96, MS (Fig. 6.19):
(m/z) 242, 212, 165, 158.
2-amino-4-(3-methoxyphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6P)
N
O
NH2
OCH3
N
(Fig. 6.20)
(6P) Brown solid; Yield=86%; M.P. = 140 0C; IR (KBr, cm-1) 3078, 2930,
2229, 1721, 1681, 1229. 1H NMR (300 MHz, DMSO d6) δ (ppm): 8.46 (s, 1H,
N-H), 8.036-8.032 (d, 1H, Ar-H), 7.85-7.82 (m, 3H, Ar-H), 7.46-7.40 (m, 3H,
Ar-H), 7.16-7.13 (m, 2H, Ar-H), 3.80 (s, 3H, O-CH3), 13C NMR (300 MHz,
DMSO d6) δ (ppm): 190.25, 189.14, 159.72, 147.15, 142.58, 140.01, 135.41,
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
230
135.23, 132.04, 130.57, 129.62, 127.71, 123.91, 123.35, 121.35, 120.77,
116.91, 114.07, 82.97, 55.52.
2-amino-4-(3,4-dimethoxyphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6Q)
N
O
NH2
O
OCH3
CH3
N
(Fig. 6.21)
(6Q) Green solid; Yield=73%; M.P. = 190 0C; IR (Fig. 6.22) (KBr, cm-1) 3088,
2922, 2222, 1713, 1676, 1275. 1H NMR (Fig. 6.23) (300 MHz, DMSO d6) δ
(ppm): 8.69 (s, 1H, N-H), 8.35 (s, 1H, Ar-H), 8.05-8.02 (d, 1H, Ar-H), 7.97-
7.94 (m, 2H, Ar-H), 7.63-7.59 (d, 1H, Ar-H), 7.23-7.15 (m, 2H, Ar-H), 3.79 (s,
1H, N-H), 3.91-3.88 (m, 6H,o-CH3 ), 13C NMR (Fig. 6.24) (300 MHz, DMSO
d6) δ (ppm): 189.82, 189.20, 160.66, 154.44, 153.92, 148.74, 148.32, 146.41,
135.68, 135.54, 131.10, 127.27, 126.10, 124.13, 122.78, 115.78, 114.04,
112.01, 76.70, 56.06, 55.49, MS (Fig. 6.25):(m/z) 293, 279, 263, 251.
2-amino-4-(naphthalen-1-yl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6S)
N
O
NH2
N
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
231
(Fig. 6.26)
(6S) Yellow solid; Yield=79%; M.P. = 155 0C; IR (KBr, cm-1) 3051, 2923,
1680, 1591, 1229. 1H NMR (300 MHz, DMSO d6) δ (ppm): 8.59 (s, 1H, N-H),
8.54-8.52 (d, 1H, Ar-H), 8.20-8.18 (d, 2H, Ar-H), 8.08-8.04 (m,2H, Ar-H),
7.99-7.97 (m, 3H, Ar-H), 7.74-7.61 (m, 4H, Ar-H), 13C NMR (300 MHz,
DMSO d6) δ (ppm): 189.49, 188.93, 153.50, 143.58, 141.41, 140.49, 139.92,
139.81, 138.69, 136.75, 135.90, 135.72, 135.54, 135.34, 129.23, 128.93,
124.11, 122.86, 122.76, 114.38, 113.00, 75.96.
2-amino-4-(anthracen-9-yl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (Table 6.3, Entry 6T)
N
O
NH2
N
(Fig. 6.27)
(6T) Red solid; Yield=76%; M.P. = 105 0C; IR (Fig. 6.28) (KBr, cm-1) 3050,
2923, 1687, 1552, 1249. 1H NMR (Fig. 6.29) (300 MHz, DMSO d6) δ (ppm):
11.44 (s, 1H, N-H), 9.01-8.95 (m, 4H, Ar-H), 8.72 (s, 1H, N-H), 8.20-8.14 (m,
m, 3H, Ar-H), 7.63-7.49 (m, 6H, Ar-H), 13C NMR (Fig. 6.30) (300 MHz,
DMSO d6) δ (ppm): 194.27, 188.39, 187.41, 142.00, 140.58, 140.01, 136.06,
136.00, 135.29, 134.75, 131.38, 130.68, 130.52, 129.37, 129.31, 129.12,
128.80, 127.34, 126.75, 125.87, 125.74, 125.65, 124.42, 123.50, 123.42,
123.01.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
232
Section II
ANTIMICROBIAL ACTIVITY
6. II.1 Introduction
The consumption of pesticides for pest control in agriculture picked
after the introduction of high yielding varieties in 1966-67. The earliest
fungicides were inorganic materials like sulphur, lime-sulphur & mercury
compounds. Elemental sulphur has been recognized as fungicide for at least
170 years. The latter is the most important of the copper fungicide; Bordeaux
mixture was discovered by Millarded (1882). The majority of protestants
fungicides are directly toxic to fungi & so will show up as active against spore
germination in-vitro tests. Development of systemic fungicides largely arisen
from antibacterial action of Penicillium mould by Fleming (1929) & of
Prontosil by Domagt (1935) & number of bactericides & antibiotics were
examined as potential systemic fungicides eg. Sulpholamides.
This discovery of organic pesticides provides man with new & powerful
weapon against insect pests diseases & weeds. So, there is need of work on
new synthetic derivatives. The specific aim of the study is, due to toxic
pesticides & their hazards in ecosystem some less toxic derivatives to the non
target organisms to be synthesized.
They cause damage of millions of dollars to crop by causing plat
diseases. It is necessary to apply certain chemical which is toxic to certain
target fungi but harmless to human beings.
6. II.2 Materials and Method
6. II.2.1 Strains used for Antifungal Activity
The evaluation of antifungal activity we have used Aspergillus niger and
Candida albicans. The details of the strains are given in the (chapter 5).
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
233
6. II.2.2 Strains used for Antibacterial Activity
The evaluation of antibacterial activity we have used Staphylococcus
aureus (ATCC 6538) from gram-positive group of bacteria and Escherichia
coli (ATCC 8739) selecting from gram-negative bacteria. The details of the
strains are given in the (Chapter 4).
6. II.2.3 Compounds Selected for Activity
The compounds with structural variability which showing good result in
preliminary study are selected for antifungal and antibacterial activity. The
compounds 6A, 6I, 6N, 6Q and 6T (Table 6.4) are used for further detail study.
(Table 6.4) The compounds selected for antifungal and antibacterial activity.
Sr. No. Entry Structure
1 6A
N
O
NH2
O2N
N
2 6I
N
O
NH2
OH
N
3 6N
S
N
O
NH2
N
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
234
4 6Q
N
O
NH2
O
OCH3
CH3
N
5 6T
N
O
NH2
N
6. II.3 Experimental Procedure for Antifungal Screening
Agar Well Diffusion Method:
Antifungal activity was tested by agar well diffusion method. The
procedure is discussed in the (Chapter 5).
6. II.4 Experimental Procedure for Antibacterial Screening
Agar Well Diffusion Method:
Antibacterial activity was tested by agar well diffusion method on
nutrient agar plates. The organisms used in the present study were obtained
from the laboratory stock. The procedure is discussed in the (Chapter 4).
6. II.5 Results and Discussion
The zone of inhibition at two different concentrations was recorded. These
are reported in the (Table 6.5) and (Table 6.6) as shown in the below.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
235
(Table 6.5) The Antifungal Screening: zone of inhibition for different
compounds.
Sr.
No. Entry
Zone of Inhibition (mm)
Aspergillus niger Candida albicans
50 (µg/ml) 100 (µg/ml) 50 (µg/ml) 100 (µg/ml)
1 6A 6a 14 -- 4
2 6I -- 2 11 18
3 6N -- 3 6 9
4 6Q 2 5 5 8
5 6T -- 4 4 6
8 Standard (Bavistin) (10µg/ml)
30 34
9 Solvent (DMSO) -- -- -- --
10 Control -- -- -- --
a Zone inhibition values are given in millimeters, ‘--’ no inhibition, b NT= Not taken
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
236
(Table 6.6) The Antibacterial screening: zone of inhibition for different
compounds.
Sr.
No. Entry
Zone of Inhibition (mm)
Staphylococcus aureus Escherichia coli
50 (µg/ml) 100 (µg/ml) 50 (µg/ml) 100 (µg/ml)
1 6A -- -- 3 5
2 6I -- -- 8 17
3 6N -- -- 3 4
4 6Q 2 4 6 7
5 6T 8a 12 4 8
8 Standard Ampicillin (10µg/ml)
23 20
9 Solvent (DMSO) -- -- -- --
10 Control -- -- -- --
a Zone inhibition values are given in millimeters, ‘--’ no inhibition,
The photograph showing zone of inhibition of compound (6A) (Fig.
6.31) against fungus Aspergillus niger, compounds (6I and 6T) (Fig. 6.32)
against fungus Candida albicans and compound (6I) (Fig. 6.33) against fungus
Escherichia coli for 50 (µg/ml) and 100 (µg/ml) concentrations.
Chapter 6: Synthesis of
(Fig. 6.3
(Fig. 6.32)
Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
237
(Fig. 6.31) The Zone of Inhibition for Compound(Table 6.3, Entry 6A)
) The Zone of Inhibition for Compound 6I and 6T(Table 6.3, Entry 6I and 6T)
carbonitrile derivatives and their
antimicrobial activity
The Zone of Inhibition for Compound 6A
6I and 6T
Chapter 6: Synthesis of 5-oxo-5
(Fig. 6.33) The Zone of Inhibition for Compound
The structure of most active compounds (
compound (6I) (Fig. 6.34)
coli, and (6T) against Staphylococcus aureus
(Fig. 6.34
Candida albicans
5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
238
The Zone of Inhibition for Compound 6I
(Table 6.3, Entry 6I)
most active compounds (6A) against Aspergillus
) active against Candida albicans and Escherichia
Staphylococcus aureus are shown.
4) The Compound 6I active against
Candida albicans and Escherichia coli. (Table 6.3, Entry 6I)
carbonitrile derivatives and their
antimicrobial activity
Aspergillus niger,
Escherichia
(Table 6.3, Entry 6I)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
239
6. II.6 Conclusions
First the synthesis of desired 5-oxo-5H-indeno[1,2-b]pyridine-3-
carbonitrile were done by four component reaction of aromatic aldehydes,
malanonitrile, 1,3-indandione and ammonium acetate at room temperature
using CuO-NPs as catalyst in water as eco-friendly solvent.
In the section second the antifungal activity and antibacterial activities
were carried out. For antifungal activity was screened against the two fungal
species Aspergillus niger and Candida albicans. The agar well diffusion
method is used for the antifungal activity. The zone of inhibition at two
different concentrations was recorded after the 48 hr. The compound 2-amino-
4-(3-nitrophenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile (6A) is good
against A. niger with zone of inhibition 14 mm and compound 2-amino-4-(4-
hydroxyphenyl)-5-oxo-5H-indeno[1,2-b]pyridine-3 carbonitrile (6I) against C.
albicans with18 mm zone of inhibition at 100 µg/ml concentration.
The antibacterial activity was carried out against two bacterial species S.
aureus and E. coli. The disc diffusion method is used for the antibacterial
activity. The zone of inhibition at two different concentrations was recorded
after the 24 hr. The compounds 2-amino-4-(4-hydroxyphenyl)-5-oxo-5H-
indeno[1,2-b]pyridine-3-carbonitrile (6I) is active against E. coli with zone of
inhibition 17 mm and compound 2-amino-4-(anthracen-9-yl)-5-oxo-5H-
indeno[1,2-b]pyridine-3-carbonitrile (6T) is most active against S. aureus with
zone of inhibition 12 mm at 100µg/ml concentration.
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
240
(Fig
. 6.3
) IR
Spe
ctru
m o
f 2-
Am
ino-
4-(3
-nit
roph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile (
Tab
le 6
.3, E
ntry
6A
)
(Fig
. 6.7
) IR
Spe
ctru
m o
f 2-
Am
ino-
4-(4
-hyd
roxy
phen
yl)-
5-ox
o-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
((T
able
6.3
, Ent
ry 6
I)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
241
(Fig
. 6.8
) 1 H
NM
R S
pect
rum
of
2-A
min
o-4-
(4-h
ydro
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6I)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
242
(Fig
. 6.9
) 13
C N
MR
Spe
ctru
m o
f 2-
Am
ino-
4-(4
-hyd
roxy
phen
yl)-
5-ox
o-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
(T
able
6.3
, Ent
ry 6
I)
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
243
(Fig
. 6.1
0) M
ass
Spec
trum
of
2-A
min
o-4-
(4-h
ydro
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile (
Tab
le 6
.3, E
ntry
6I)
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
244
(Fig
. 6.1
2) I
R S
pect
rum
of
2-A
min
o-4-
(3,4
-dih
ydro
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6L
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
245
(Fig
. 6.1
3) M
ass
Spec
trum
of
2-A
min
o-4-
(3,4
-dih
ydro
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6L
)
M. W
. = 3
29
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
246
(Fig
. 6.1
7) I
R S
pect
rum
of
2-A
min
o-5-
oxo-
4-(t
hiop
hen-
2-yl
)-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
(T
able
6.3
, Ent
ry 6
N)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
247
(Fig
. 6.1
7) 1 H
NM
R S
pect
rum
of
2-A
min
o-5-
oxo-
4-(t
hiop
hen-
2-yl
)-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
(T
able
6.3
, Ent
ry 6
N)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
248
(Fig
. 6.1
8) 13
C N
MR
Spe
ctru
m o
f 2-
Am
ino-
5-ox
o-4-
(thi
ophe
n-2-
yl)-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6N
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
249
(Fig
. 6.1
9) M
ass
Spec
trum
of
2-A
min
o-5-
oxo-
4-(t
hiop
hen-
2-yl
)-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
(T
able
6.3
, Ent
ry 6
N)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
250
(Fig
. 6.2
2) I
R S
pect
rum
of
2-A
min
o-4-
(3,4
-dim
etho
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6Q
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
251
(Fig
. 6.2
3) 1 H
NM
R S
pect
rum
of
2-A
min
o-4-
(3,4
-dim
etho
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6Q
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
252
(Fig
. 6.2
4) 13
C N
MR
Spe
ctru
m o
f 2-
Am
ino-
4-(3
,4-d
imet
hoxy
phen
yl)-
5-ox
o-5H
-ind
eno[
1,2-
b]py
ridi
ne-3
-car
boni
trile
(T
able
6.3
, Ent
ry 6
Q)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
253
(Fig
. 6.2
5) M
ass
Spec
trum
of
2-A
min
o-4-
(3,4
-dim
etho
xyph
enyl
)-5-
oxo-
5H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6Q
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
254
(Fig
. 6.2
8) I
R S
pect
rum
of
2-A
min
o-4-
(ant
hrac
en-9
-yl)
-5-o
xo-5
H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6T
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
255
(Fig
. 6.2
9) 1 H
NM
R S
pect
rum
of
2-A
min
o-4-
(ant
hrac
en-9
-yl)
-5-o
xo-5
H-i
nden
o[1,
2-b]
pyri
dine
-3-c
arbo
nitr
ile
(Tab
le 6
.3, E
ntry
6T
)
Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
256
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Chapter 6: Synthesis of 5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives and their
antimicrobial activity
257
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