Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds

Article abstract of DOI:10.1002/aoc.4173

We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH₂, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.

Full text of DOI:10.1002/aoc.4173

Received: 25 July 2017
DOI: 10.1002/aoc.4173
Revised: 12 October 2017
Accepted: 12 October 2017
F U L L P A P E R
Pd‐NHC catalysed Carbonylative Suzuki coupling reaction
and its application towards the synthesis of biologically
active 3‐aroylquinolin‐4 (1H)‐one and acridone scaffolds
Prasanjit Ghosh | Bhaskar Ganguly | Sajal Das
Department of Chemistry, University of
We have unfolded a convenient and mild protocol for the synthesis of diaryl
ketones via Pd‐ NHC catalysed carbonylative Suzuki coupling reaction.
Notably, this method offers advantages like no use of toxic CO gas, shorter
reaction time, high yield, and broad substrate scope. Several sensitive func-
tional groups (like‐COMe, ‐COOMe, ‐F, ‐Cl, ‐Br, ‐NH2, ‐CN) are well tolerated
in this reaction. In addition, we have also demonstrated a new efficient route
for the synthesis of biologically active and pharmaceutically important 2‐
substituted 3‐Aroylquinolin‐4(1H)‐ones and acridone scaffolds.
North Bengal, Darjeeling 734013, West
Bengal, India
Correspondence
P. Ghosh, B. Ganguly and S. Das,
Department of Chemistry, University of
North Bengal, Darjeeling, 734013, West
Bengal, India.
Email: prasanjitmeister@yahoo.com;
sajal.das@hotmail.com
Funding information
Science and Engineering Research Board,
Grant/Award Number: EMR/2016/001250
KEYWORDS
3‐aroyl quinolin‐4(1H)one, Acridone, Carbonylative Suzuki coupling, Diaryl ketones, Pd‐NHC
1 | INTRODUCTION
methodologies for the synthesis of diaryl ketone motifs
is of great importance in view of medicinal chemistry.
Numerous photosensitizers, natural products, advanced
organic materials and pharmaceutically apposite agents
are comprised of diaryl ketone units.[1] Some of the top‐
selling drugs, for instance, Evista,[2] Tricor[3] and Sector[4]
contain diaryl ketone core unit. On other hand, heterocy-
cles are important structural motifs found in many natu-
ral products, functional molecules and bioactive
compounds.[5a] Thus, the hybrid compounds, comprising
of both diaryl ketones and heterocyles, are of the interest
in medicinal chemistry. Few reported compounds con-
taining such hybrid framework are represented in
Figure 1.[5b, c] Among them, chromone derivatives, espe-
cially 4‐quinolones and acridones, comprised a large seg-
ment of the biologically active compounds reported.[6]
Recently, Botta and Goggiamani unfolded the synthesis
of 2‐Substituted 3‐Aroylquinolin‐4(1H)‐ones via Pd‐
catalysed carbonylative cyclization of N‐(2‐iodoaryl)
enaminones.[7] The 2‐Substituted 3‐Aroylquinolin‐4(1H)‐
one derivatives has proved itself as inhibitor of Hedgehog
(Hh) signaling pathway in vitro and suppress the growth
of MB cells which opened a new avenue for the discovery
of anticancer lead compounds. Development of newer
Traditionally, diaryl ketones are easily prepared by
Friedel‐Crafts acylations, acylative Suzuki couplings, and
nucleophilic additions of an organometallic to a carbonyl
moiety. In 1997, Bumagin et al. synthesized the aryl
ketones via Pd‐catalysed cross‐coupling reactions of acid
chlorides.[8] Afterwards, this methodology was extended
towards the acylative Suzuki coupling with esters[9], anhy-
drides[10] and carboxylic acid in the presence of an
activating agents.[10c, 11] Liebeskind and Srogl used cata-
lytic amount of Pd(0) salt and stoichiometric amount of
expensive Cu(I)TC [Copper(I)‐thiophene‐2‐carboxylate to
synthesize the diaryl ketones via thiolester–boronic acid
coupling.[12a–d] Very recently, Das et al. reported a method
for the synthesis of diaryl ketones via thiolester‐boronic
acid coupling in the presence of Cu and Ag salts.[12e]
However, the traditional transition metal catalysed
carbonylative cross‐coupling reactions between aryl elec-
trophiles, carbon monoxide and organometallic reagent
has been substantiated to be the more convenient route
for the synthesis of wide range of diaryl ketones. Several
aryl metal reagents such as silicon,[13] aluminium,[14]
tin[15] and magnesium[16] were frequently used for this
Appl Organometal Chem. 2017;e4173.
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https://doi.org/10.1002/aoc.4173

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GHOSH ET AL.
FIGURE 1 Some biologically active Diaryl ketone compounds
case. The main disadvantage of this carbonylative cross‐
coupling reaction is the formation diaryl by products,
especially in the case of electron deficient aryl halides.[17]
Suzuki et al. introduced a facile protocol for synthesizing
the diaryl ketones from arylboronic acid, carbon monox-
ide and aryl halides in presence of palladium catalyst.[18]
Though this method was quite effective due to the versa-
tile nature of boronic acid as it is non‐toxic, bench‐stable
and easily available, yet the essential involvement of toxic
CO gas rendered the method narrowed down its scope.
After that, several research groups studied the same reac-
tion using different palladium catalyst such as
appears much appealing and effective than any other
methods due to easy handling and in‐situ generation of
CO upon heating.
Previously, Jafarpour et al. reported the carbonylative
Suzuki coupling of aryl halides and arylboronic acid in
presence of Mo(CO)6 and Palladium acetate.[34] However,
the method requires high loading of Pd catalyst
(10 mol%), longer reaction time and high temperature.
As a part of our ongoing effort towards develop the simple
protocol for the formation of C‐C bond, herein we report a
convenient methodology for carbonylative Suzuki reac-
tion (Scheme 1) between aryl halides and arylboronic
acids in presence of our previously synthesized Pd‐NHC
catalyst (Figure 2).[35]
PdCl2(PPh3)2,[19]
PdCl2(PPh3)2/
PdCl2(dppf),[20]
Pd(OAc)2‐imidazolium salts,[21] Pd(OAc)2/ N,N‐bis(2,6‐
diisopropylphenyl)dihydroimidazolium chloride,[22] an
MCM‐41‐supported bidentate phosphane palladium com-
plex,[23] Pd(OAc)2/di‐1‐adamantyl‐n‐butylphosphane[24]
and Pd/thiourea.[25] In spite of their huge potentiallity,
those methods suffered from several disadvantages, like
use of air/moisture sensitive and expensive phosphane
donating ligands, longer reaction time and requirement
of high pressure equipment. Very recently, Bhanage and
Han et al. reported the Suzuki carbonylation of aryl and
heterocyclic halides using palladacyle complex, KCC‐1
supported palladium nanoparticles,[26] iron and nickel
nano particle[27] where carbon monoxide gas used as car-
bonyl source. In these protocols, high pressure of CO gas
is essentially required not only to get the good yield of
desired ketones but also to reduce the formation of
byproducts. A search in the literature revealed that
several compounds like formic acid,[28] formates,[29]
chloroform,[30] aldehydes[31] and other CO surrogates[32]
have been used as CO source. In addition, few metal
carbonyls were also used as CO source.[33] Above all, the
incorporation of carbon monoxide via metal carbonyl
Further, we apply this protocol for the synthesis of
biologically active 2‐substituted‐3‐Aroylquinolin‐4(1H)‐
one and acridone scaffolds (Scheme 1).
2 | RESULTS AND DISCUSSION
To investigate the feasibility of the reaction, we com-
menced our journey with the carbonylative cross coupling
reaction between phenylboronic acid and iodobenzene
using Pd‐NHC (1 mol%) as catalyst, K2CO3 as base in
DMF. After 24 h of reaction, we obtained only 15% yield
of the desired diaryl ketone (Table I; entry 1). Then, we
screened solvents and found anisole as a media, served
the better yields of diaryl ketone compared to other
solvents like DMF, Toluene, 1,4‐dioxane and THF
(Table 1; entries 1‐5). Combination of K2CO3 and anisole
proved to be best suited for this carbonylative Suzuki cou-
pling (Table 1; entry 4). Most surprisingly, the reaction
completed within 1 h only and resulted in 85% of the
desired product. We next turned our attention to choose

GHOSH ET AL.
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SCHEME 1 Our approach for the
synthesis of diaryl ketone scaffolds
obtained in moderate to good yield upon using commonly
available Pd‐catalysts. It was also found that 95 °C is the
optimal reaction temperature (Table 1; entry 4) for this
coupling reaction. At low temperature, yield of the diaryl
ketone decreases might be due to the unavailability of suf-
ficient carbon monoxide (Table 1; entry 13, 14). The same
reaction at 120 °C resulted in 84% yield of product 2A1
within 1 h (Table 1; entry 15). Combination of Pd‐NHC
(1 mol %) and K2CO3 (3 equiv.), in anisole at 95 °C, was
found to be optimal for the carbonylative cross coupling
reaction and led the product 2A1 (benzophenone) in 85%
yield after only 1 h.
FIGURE 2 Structure of Pd‐NHC catalyst
the better base other than K2CO3. Inferior results of desired
product was obtained upon using common bases like DBU,
t‐BuOK, Cs2CO3 and Et3N (Table 1; entries 6‐9).
Then, we screened out the catalytic activity of different
palladium catalyst (Table 1; entries 10‐12) as well as reac-
tion temperature (Table 1; entries 4, 13‐15). The product
TABLE 1 Optimization of the reaction conditionsa
Entry
1
Catalyst (mol %)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
Pd(OAc)2 (5)
PdCl2 (5)
Solvent
DMF
Base
Temp (° c)
Time (h)
Yield (%)b
15
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3s
t‐BuOK
DBU
95
95
95
95
95
95
95
95
95
95
95
95
80
60
120
24
24
24
1
2
THF
20
3
1,4‐dioxane
Anisole
Toluene
Anisole
Anisole
Anisole
Anisole
Anisole
Anisole
Anisole
Anisole
Anisole
Anisole
NR
85
4
5
24
24
24
24
24
7
30
6
10
7
NR
10
8
Cs2CO3
Et3N
9
25
10
11
12
13
14
15
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
64
7
68
Pd2(dba)3 (5)
Pd‐NHC (1)
Pd‐NHC (1)
Pd‐NHC (1)
7
73
4
65
12
1
52
84
aReaction conditions: 0.25 mmol of iodobenzene, 0.375 mmol of phenylboronic acid, base (3 equiv.), Mo(CO)6 (1 equiv., 66 mg), were heated under N2 atm.
bYield = isolated yields after column chromatography.

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GHOSH ET AL.
SCHEME 2 Substrate scope of various
aryl iodides and (het)arylboronic acids in
the carbonylative Suzuki coupling*
*Reaction condition: 0.25 mmol of iodoarenes, 0.375
mmol of boronic acids, base (0.75 mmol, 104 mg), Pd‐
NHC catalyst (2.5 mg, 1 mol%) and Mo(CO)6 (1 equiv.,
66 mg) were heated 95°C under N2‐ atmosphere in
anisole. bIsolated yield after column chromatography.

GHOSH ET AL.
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The representative results of this carbonylative Suzuki
did not afford the corresponding diaryl ketone even after
24 h stirring (Scheme 2, entries 2A9 and 2A19) at 95 °C.
We also found the smooth participation of heterocyclic
iodoarene (2‐iodothiophene) in this reaction and
resulted in the good yield of the corresponding product
(Scheme 2, entry 2A15).
To study the scope of this protocol, a broad array of
arylboronic acid possessing both electron donating and
electron withdrawing groups were allowed to react with
various iodoarenes under the optimized conditions
(Scheme 2). Our protocol proved to be quite compatible
with various functional groups like methoxy, chloro,
fluoro, ester and cyano. 1‐naphthyl and 2‐naphthylboronic
acid were individually coupled with iodobenzene and 4‐
iodotoluene and afforded the desired products with high
yields (Scheme 2; entries 2A22, 2A11, 2A28 and 2A29). We
also observed that a heterocyclic iodoarenes (2‐iodo
thiophene) coupled with 4‐methoxyphenyl boronic acid
effectively (Scheme 2; entry 2A30). Importantly, 1‐
iodonaphthalene quite successfully underwent the
reaction between different aryliodides, phenylboronic acid
and Mo(CO)6 are summarized in Scheme 2. It is clear from
the results that iodoarenes having electron withdrawing
and electron releasing group were equally participated in
the carbonylative Suzuki reaction with phenylboronic
acid without any difficulties (Scheme 2; entries 2A1‐
2A19). Aryl iodides containing electron donating groups
like –Me, ‐OMe, ‐NH2 reacted efficiently with
phenylboronic acid and gave corresponding unsymmetri-
cal ketones in high yield (Scheme 2, entries 2A3, 2A7,
2A10, 2A2, 2A18, and 2A6). On the other hand, 4‐
iodoacetophenone took longer time (5 h) and resulted in
80% yield of the desired product (Scheme 2, entry 2A4).
This might be due to the presence of electron withdrawing
group which slow down the reaction. Aspect of steric hin-
drance in making the diaryl ketones via this present proto-
col was also studied. Ortho substituted (‐F, ‐NH2, ‐Me, ‐Cl,
‐Br, ‐CF3 and ‐OMe) iodoarenes afforded the correspond-
ing diaryl ketones in moderate to good yields (Scheme 2,
entries 2A5, 2A6, 2A7, 2A13, 2A14, 2A17, 2A18).
carbonylative
Suzuki
coupling
with
4‐fluoro
Whereas 1‐naphthyl iodoarenes responded very well
and gave 90% of the desired product in 1 h (Scheme 2,
entry 2A11). We then moved to explore the possibility
for making diketo compounds using our protocol. Reac-
tion of 1,3‐ and 1,2‐diiodo benzene with phenylboronic
acid and Mo(CO)6 afforded the bis couple product in
70% and 81% yield, respectively (Scheme 2; entry 2A8
and 2A16). Isolation of the product 2A16 in 81% yield fur-
ther justified that the steric hindrance did not affect the
reaction. Surprisingly, 3‐iodo aniline and 2‐iodophenol
phenylboronic acid and 2‐naphthylboronic acid (Scheme 2;
entries 2A33 and 2A34). Unfortunately, 4‐cyano
phenylboronic acid afforded only 32% yield of the desired
diaryl ketone when it coupled with normal iodobenzene
(Scheme 2; entry 2A36). To our delight, iodoarene
possessing nitro group at meta position did not hamper
the process and coupled with both electron deficient and
electron rich arylboronic acid (Scheme 2; entries 2A24,
2A27). More interestingly, 4‐iodotoluene coupled with p‐
tolylboronic acid excellently and furnished the
SCHEME 3 Scope of carbonylative
Suzuki coupling in 4‐quinolone scaffold†
†Reaction conditions: 0.25 mmol of 3‐iodo
substituted 4‐quinolone (86 mg), 0.375 mmol
of substituted arylboronic acid, base (3
equiv.), Mo(CO)6 (66 mg, 1 equiv.) and Pd‐
NHC (2.5 mg, 1 mol%) were heated at 95°C
b
under N2 atmosphere in anisole. Isolated
yield after column chromatography.

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GHOSH ET AL.
corresponding product 2A37 (85%) in a very short span.
Similarly, we also prepared the symmetrical diaryl car-
bonyls of 4‐chloro‐iodobenzene in 88% yield (Scheme 2;
entry 2A38).
Substituted 2‐iodo aniline and 2‐bromo phenylboronic
acid are selected as coupling partners in this case. Without
purifying the intermediate diaryl ketones, we turned our
attention to cyclize them under refluxing conditions in
presence of t‐BuOK and getting isolated the biologically
active acridone moieties in excellent yields (Scheme 4,
entries 5a‐5c).
A plausible reaction pathway for Carbonylative Suzuki
cross coupling reactions has been shown in Scheme 5. The
reaction initiated with generation of active Pd(0) species.
It underwent an oxidative addition with aryl iodides to
3 | APPLICATIONS
As a part of our ongoing interest towards the synthesis of
functionalized 4‐quinolones.[35c, 36] we further explored
the scope of this coupling reaction for the preparation of
biologically active 4‐quinolone scaffolds. Very recently
Alfonsi et al. reported a palladium catalysed sequential
synthesis of 3‐aroylquinolin‐4(1H) one derivatives from 2‐
iodoaniline.[7] But the method requires the use of expensive
phosphine ligand, high pressure (20 atm.) of toxic CO gas,
high temperature and longer reaction time (72 h) which
limit the broad application scope of the method. We took
the challenge and decided to applyour protocol in synthesis
of 3‐aroylquinolin‐4(1H) one derivatives (Scheme 3).
Reaction between 3‐iodo‐2‐aryl substituted 4‐quino-
lone and arylboronic acid at our optimized condition
resulted in the good yield of desired products within 10‐
15 h. It has been found that both electron withdrawing
and electron donating arylboronic acid effectively
underwentthereactionandresultedinthedesiredproducts
in 72% and 63%, respectively (Scheme 3; entries 4b and 4c).
Next, we again applied our protocol in the modular
synthesis of pharmaceutically important acridone scaffolds
in one pot as shown in scheme 4. Acridones are widely
existed in antifungal, antileishmanial, DNA‐intercalating
anticancer drugs[6b] and also as fluorescent labels.[37]
SCHEME 5 Plausible reaction pathway for the catalytic cycles of
Carbonylative Suzuki coupling reaction
SCHEME 4 Synthesis of
pharmaceutically important acridone
scaffolds‡
‡Reaction conditions: Step‐I – 0.25 mmol of
substituted 2‐iodo aniline, 0.375 mmol of 2‐
bromo phenylboronic acid (76 mg), base (3
equiv.), Mo(CO)6 (66 mg, 1 equiv.) and Pd‐
NHC were heated at 95°C under N2 atmo-
sphere in anisole for 3 h; Step‐II – t‐BuOK (3
equiv.) reflux at 130°C in DMSO for next 8 h.
b Isolated yield after column chromatography.

GHOSH ET AL.
7 of 12
generate an aryl palladium intermediate (A). Conse-
quently, the aryl palladium intermediate get converted into
the acylpalladium species (B) in the presence of CO which
was generated in situ upon decomposition of Mo(CO)6
under the reaction condition. Later, the complex B
participated in transmetallation reaction with arylboronic
to form new complex C. Finally, the desired diarylketone
product is obtained after the reductive elimination with
the concomitant generation of Pd (0) species, which
proceeds to participate in the next catalytic cycle.
Mo(CO)6 (0.25 mmol, 66 mg), Pd‐NHC (1 mol%, 2.5 mg)
and anisole (2 ml) were taken in a sealed tube under N2
atmosphere and heated at 95 °C. The reaction was
continued for 1 h to several hours for completion of the
reaction. After monitoring the TLC analysis, the reaction
mixture was diluted with 30 ml water and the organic
layer was extracted with DCM (30 ml). Then, it was dried
over anhydrous sodium sulphate and concentrated under
reduced pressure. The crude residue was purified through
column chromatography using petroleum ether and ethyl
acetate as an eluent.
4 | CONCLUSIONS
5.3 | Preparation of 3‐iodo‐2‐ phenyl
substituted 4‐quinolones (3a)
In summary, we have developed a mild and efficient pro-
tocol for the synthesis of diaryl ketones via Pd‐NHC
catalysed carbonylative Suzuki coupling reaction between
the commercially available iodoarenes and arylboronic
acids in the presence of Mo(CO)6. This new strategy offers
several advantages such as, non‐requirement of toxic CO
gas, shorter reaction time, good to excellent yield of the
desired products and broad substrate scope. Most
importantly, this protocol requires only 1 mol% of
palladium catalyst which is much lower than the
previously reported methods. Noteworthy, in this protocol
various sensitive functional groups are found well
tolerated (‐COMe, ‐COOMe, ‐NH2, ‐CN, ‐Br, ‐F, ‐Cl).
The present methodology could be applied for the
synthesis of biologically active 2‐ phenyl substituted‐3‐
Aroylquinolin‐4(1H)‐ones and acridone motifs.
Initially, 2‐aryl quinolin‐4(1H)‐one (0.25 mmol), iodine
(2 equiv.) and sodium carbonate (1.5 equiv.) in THF
(2 ml) was stirred at room temperature for 18 hours.
Then, the reaction mixture was quenched with sodium
thiosulphate and the precipitate was collected by filtration
and washed with ice‐cold water. Afterwards, the crude
product was purified through column chromatography.
5.4 | Preparation of 2‐phenyl substituted‐
3‐aroylquinolin‐4(1H)‐ones from the
carbonylative Suzuki coupling of 3a (4a‐4c)
Initially, 3‐iodo‐4‐quinolone derivatives (0.25 mmol,
86 mg), arylboronic acid (0.375 mmol), K2CO3 (0.75 mmol,
104 mg), Mo(CO)6 (0.25 mmol, 66 mg), Pd‐NHC (1 mol%,
2.5 mg) and anisole (2 ml) were taken in a sealed tube
under N2 atmosphere and heated at 95 °C. The reaction
was continued for 10 h to 15 h for completion of the
reaction. After monitoring the TLC analysis, the reaction
mixture was diluted with 30 ml water and the organic
layer was extracted with ethyl acetate (30 ml). Then, it
was dried over anhydrous sodium sulphate and concen-
trated under reduced pressure. The crude residue was
purified through column chromatography using
petroleum ether and ethyl acetate as an eluents.
5 | EXPERIMENTAL SECTION
5.1 | General considerations
Unless stated otherwise, all reagents such as various
Iodoarenes, aryl(Het)boronic acid, K2CO3, Anisole,
Mo(CO)6 and solvents were used as received from com-
mercial suppliers. NMR spectra were recorded on
300 MHz spectrometer at 298 K with calibration done
on the basis of solvent residual peak. Products were puri-
fied using column chromatography on silica gel (60‐120
mesh). Ethyl acetate and petroleum ether (60‐80 °C) were
used as eluents. Progress of reaction was monitored using
silica gel TLC.
5.5 | Preparation of pharmaceutically
important acridone scaffolds (5a‐5c)
Primarily, substituted 2‐iodo aniline (0.25 mmol), 2‐
bromophenylboronic acid (0.375 mmol, 76 mg), K2CO3
(0.75 mmol, 104 mg), Mo(CO)6 (0.25 mmol, 66 mg), Pd‐
NHC (1 mol%, 2.5 mg) and anisole (2 ml) were taken in
a sealed tube under N2 atmosphere and heated at 95 °C.
The reaction was continued for 3 h for completion of the
reaction. After monitoring the TLC analysis, the reaction
mixture was diluted with 30 ml water and the organic
layer was extracted with DCM (30 ml). Then, it was dried
5.2 | Preparation of Biaryl ketones from
the Carbonylative Suzuki coupling of
various iodoarenes and aryl(het)boronic
acids (2A1‐2A38)
Initially, various iodoarenes (0.25 mmol), aryl(Het)
boronic acid (0.375 mmol), K2CO3 (0.75 mmol, 104 mg),

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GHOSH ET AL.
over anhydrous sodium sulphate and concentrated under
reduced pressure. In the next step, the crude reaction mix-
ture was refluxed in DMSO (5 ml) at 130 °C under basic
condition (t‐BuOK, 3 equiv.) for 8 h. After monitoring
the TLC analysis, the reaction mixture was diluted with
30 ml water and the organic layer was extracted with ethyl
acetate (30 ml). Then, it was dried over anhydrous sodium
sulphate and concentrated under reduced pressure. The
crude residue was purified through column chromatogra-
phy using petroleum ether and ethyl acetate as an eluent.
75 MHz) ẟ 19.9, 125.9, 128.5, 129.3, 130.1, 130.8, 131.4,
134.0, 136.2, 137.5, 138.8, 198.2.
1,3‐Phenylenebis(phenylmethanone) (2A8)[40a]
:
1
White solid, Yield = (70%, 50.0 mg), H NMR (DMSO‐
d6, 300 MHz) ẟ 7.57‐7.62 (m, 1H), 7.68‐7.70 (m, 3H),
7.79‐7.82 (m, 3H), 7.90‐8.00 (m, 4H), 8.00‐8.04 (m, 1H),
8.05‐8.08 (m, 2H), 13C NMR (DMSO‐d6, 75 MHz) ẟ
129.1, 129.7, 130.2, 131.2, 133.5, 133.9, 136.9, 137.5, 195.5.
Phenyl (m‐tolyl)methanone (2A10)[12e]: Colourless
liquid, Yield = (88%, 43.1 mg), 1H NMR (CDCl3,
300 MHz) ẟ 2.43 (s, 3H), 7.37‐7.40 (m 2H), 7.49‐7.51 (m,
2H), 7.57‐7.64 (m, 3H), 7.79‐7.82 (m, 2H), 13C NMR
(CDCl3, 75 MHz) ẟ 20.8, 126.8, 127.6, 127.7, 129.5,
130.0, 131.8, 132.6, 137.2, 137.3, 137.6, 196.4.
5.6 | Physical characteristics and spectral
data of compounds
Benzophenone (2A1)[12e]: White solid, Yield = (85%,
39 mg), 1H NMR (CDCl3, 300 MHz) ẟ 7.47‐7.53 (m, 4H),
7.58‐7.64 (m, 2H), 7.80‐7.84 (m, 4H); 13C NMR (CDCl3,
75 MHz) ẟ 128.3, 130.1, 132.4, 137.6, 196.8.
(Naphthalen‐2‐yl)(phenyl)methanone (2A11)[12e]
:
Colourless oil, Yield = (90%, 52.2 mg and 74%,
1
40.7 mg), H NMR (CDCl3, 300 MHz) ẟ 7.45‐7.64 (m,
7H), 7.88‐7.97 (m, 3H), 8.01‐8.03 (m, 1H), 8.10‐8.14 (m,
1H); 13C NMR (CDCl3, 75 MHz) ẟ 124.4, 125.7, 126.5,
127.3, 127.97, 128.4, 128.51, 130.5, 131.0, 131.4, 133.3,
133.7, 138.3, 198.1.
(4‐methoxy phenyl) phenyl methanone (2A2)[12e]
:
White solid, Yield = (82%, 43.5 mg and 83%, 44 mg),1H
NMR (CDCl3, 300 MHz) ẟ 3.89 (s, 3H), 6.95‐6.98 (m, 2H),
7.44‐7.49 (m, 2H), 7.53‐7.59 (m, 1H), 7.73‐7.76 (m, 2H),
7.77‐7.84 (m, 2H), 13C NMR (CDCl3, 75 MHz) ẟ 55.5,
113.6, 128.2, 129.7, 130.2, 131.9, 132.5, 138.3, 163.2, 195.6.
Phenyl (p‐tolyl)methanone (2A3)[12e]: White solid,
Yield = (88%, 43 mg and 87%, 42.6 mg), 1H NMR (CDCl3,
300 MHz) ẟ 2.44 (s, 3H), 7.26‐7.30 (m, 2H), 7.44‐7.50
(m, 2H), 7.54‐7.60 (m, 1H), 7.70‐7.74 (m, 2H),7.76‐7.80
(m, 2H), 13C NMR (CDCl3, 75 MHz) ẟ 21.6, 128.3,
129.0, 129.9, 130.3, 132.1, 134.9, 138.0, 143.2, 196.5.
1‐(4‐Benzoylphenyl)ethan‐1‐one (2A4)[28]: Yellow
(4‐chloro phenyl)(phenyl) methanone (2A12)[12e]
:
White solid, Yield = (83%, 45.0 mg and 88%, 47.5 mg), 1H
NMR (CDCl3, 300 MHz) ẟ 7.44‐7.52 (m, 4H), 7.58‐7.63
(m, 1H), 7.74‐7.79 (m, 4H), 13C NMR (CDCl3, 75 MHz)
ẟ 128.4, 128.6, 129.9, 131.5, 132.6, 135.9, 137.2, 138.9, 195.2.
(2‐chlorophenyl)phenyl methanone (2A13)[41]
:
Colourless oil, Yield = (76%, 41.2 mg), 1H NMR (CDCl3,
300 MHz) ẟ 7.38‐7.44 (m, 2H), 7.46‐7.51 (m, 4H), 7.60‐
7.65 (t, J = 7.5 Hz, 1H), 7.83‐7.85 (d, J = 7.8 Hz,
2H),13C NMR (CDCl3, 75 MHz) ẟ 126.7, 128.6, 129.1,
130.1, 130.2, 131.1, 131.3, 133.7, 136.4, 138.5, 195.5.
1
oil, Yield = (80%, 44.8 mg), H NMR (CDCl3, 300 MHz)
ẟ 2.69 (s, 3H), 7.50‐7.55 (m, 2H), 7.62‐7.65 (m, 1H),
7.81‐7.84 (m, 2H), 7.87‐7.90 (m, 2H), 8.07‐8.09 (m,
2H),13C NMR (CDCl3, 75 MHz) ẟ 26.8, 128.1, 128.4,
130.0, 130.1, 132.9, 136.9, 139.6, 141.4, 195.9, 197.5.
(2‐bromophenyl)(phenyl)methanone (2A14)[41]
:
1
Yellow solid, Yield = (71%, 46.3 mg), H NMR (CDCl3,
300 MHz) ẟ 7.33‐7.50 (m, 5H), 7.58‐7.66 (m, 2H), 7.80‐
7.83 (m, 2H), 13C NMR (CDCl3, 75 MHz) ẟ 119.5, 127.2,
128.6, 129.0, 130.2, 131.2, 133.2, 133.8, 136.1, 140.7, 195.9.
(2‐fluoro phenyl)(phenyl)methanone (2A5)[38]
:
Colourless liquid, Yield = (78%, 39.0 mg), 1H NMR
(DMSO‐d6, 300 MHz) ẟ 7.36‐7.42 (m, 2H), 7.55‐7.60 (m,
3H), 7.69‐7.71 (m, 2H), 7.75‐7.78 (m, 2H), 13C NMR
(DMSO‐d6, 75 MHz) ẟ 116.6, 116.9, 125.3, 125.3, 126.8,
127.0, 129.3, 129.8, 130.8, 130.9, 134.0, 134.1, 134.3,
137.1, 158.0, 161.3, 193.2.
Phenyl(thiophen‐2‐yl)methanone
(2A15)[38]
:
1
White solid, Yield = (77%, 36.2 mg), H NMR (DMSO‐d6,
300 MHz) ẟ 7.28‐7.31 (m, 1H), 7.55‐7.60 (m, 2H),
7.66‐7.73 (m, 2H), 7.82‐7.85 (m, 2H), 8.13 (dd, J = 4.8 Hz,
0.9 Hz, 1H), 13C NMR (DMSO‐d6, 75 MHz) ẟ 129.1,
129.3, 129.3, 133.0, 136.1, 136.2, 137.9, 143.2, 187.8.
(2‐aminophenyl)(phenyl)methanone
(2A6)[39]
:
1,2‐Phenylenebis(phenylmethanone) (2A16)[42]
:
1
1
Yellow solid, Yield = (65%, 32.0 mg), H NMR (CDCl3,
300 MHz) ẟ 6.00 (bs, 2H), 6.57‐6.72 (m, 1H), 6.73‐6.75
(m, 1H), 7.26‐7.32 (m, 1H), 7.43‐7.55 (m, 4H), 7.62‐7.65
(m, 2H), 13C NMR (CDCl3, 75 MHz) ẟ 115.5, 117.0,
118.2, 128.1, 129.1, 131.1, 134.2, 134.6, 140.1, 150.9, 199.1.
Phenyl(o‐tolyl)methanone (2A7)[12e]: Colourless
liquid, Yield = (89%, 43.6 mg), 1H NMR (DMSO‐d6,
300 MHz) ẟ 2.23 (s, 3H), 7.30‐7.39 (m, 3H), 7.55‐7.57
(m, 3H), 7.69‐7.72 (m, 3H), 13C NMR (DMSO‐d6,
White solid, Yield = (81%, 58.0 mg), H NMR (CDCl3,
300 MHz) ẟ 7.35‐7.41 (m, 4H), 7.49‐7.55 (m, 2H), 7.63‐7.65
(m, 4H), 7.69‐7.72 (m, 4H), 13C NMR (CDCl3, 75 MHz)
ẟ 128.3, 129.7, 129.8, 130.4, 133.0, 137.2, 140.0, 196.6.
(2‐(trifluoromethyl)phenyl)(phenyl)
methanone (2A17)[43]: Colourless liquid, Yield = (68%,
42.5 mg), 1H NMR (CDCl3, 300 MHz) ẟ 7.38‐7.41
(m, 1H), 7.44‐7.49 (m, 2H), 7.58‐7.64 (m, 3H), 7.77‐7.80
(m, 3H), 13C NMR (CDCl3, 75 MHz) ẟ 121.7, 125.4,

GHOSH ET AL.
9 of 12
126.5, 126.6, 126.7, 126.8, 128.0, 128.1, 128.5, 129.8, 130.2,
131.3, 133.8, 136.4, 138.4, 195.5.
(m, 2H), 7.70‐7.73 (m, 2H); 13C NMR (CDCl3, 75 MHz)
ẟ 21.4, 21.6, 127.2, 128.0, 128.9, 130.3, 130.3, 132.9,
135.1, 138.0, 138.1, 143.1, 196.7.
(2‐methoxyphenyl)(phenyl) methanone (2A18)[43]
:
Colourless liquid, Yield = (74%, 39.2 mg), 1H NMR
(DMSO‐d6, 300 MHz) ẟ 3.67 (s, 3H), 7.09 (dt, J = 7.5 Hz,
0.9 Hz, 1H), 7.17‐7.20 (m, 1H), 7.32 (dd, J = 7.5 Hz,
0.9 Hz, 1H), 7.49‐7.57 (m, 3H), 7.62‐7.71 (m, 3H), 13C
NMR (DMSO‐d6, 75 MHz) ẟ 56.0, 112.4, 121.0, 128.8,
129.1, 129.2, 129.7, 132.5, 133.8, 137.5, 157.1, 196.2.
(4‐chloro phenyl)(m‐nitro) methanone (2A27)[48]
:
Yellow solid, Yield = (76%, 49.6 mg and 41%, 26.8 mg),
1H NMR (CDCl3, 300 MHz) ẟ 7.51 (td, J = 4.2 Hz,
2,1 Hz, 2H), 7.70‐7.78 (m, 3H), 8.12 (td, J = 3.0 Hz,
1.5 Hz, 1H), 8.46 (qd, J = 2.4 Hz, 1.2 Hz, 1H), 8.59 (t,
J = 1.8 Hz, 1H),13C NMR (CDCl3, 75 MHz) ẟ 124.6,
126.9, 129.1, 129.4, 129.8, 131.4, 134.5, 135.3, 138.7,
140.0, 148.1, 193.0.
4‐Fluoro phenyl) phenyl methanone (2A20)[41]
:
Yellow oil, Yield = (90%, 45.0 mg),1H NMR (CDCl3,
300 MHz) ẟ 7.13‐7.20 (m, 2H), 7.46‐7.51 (m, 2H), 7.57‐
7.62 (m, 1H), 7.75‐7.79 (m, 2H), 7.82‐7.87 (m, 2H),13C
NMR (CDCl3, 75 MHz) ẟ 115.3, 115.6, 127.5, 128.3,
128.7, 129.2, 129.8, 132.4, 132.6, 132.7, 133.8, 137.5,
163.7, 167.1, 195.2.
(Naphthalen‐2‐yl)(p‐tolyl)methanone (2A28)[49]
:
1
White solid, Yield = (76%, 46.7 mg), H NMR (CDCl3,
300 MHz) ẟ 2.47 (s, 3H), 7.32 (d, J = 8.1 Hz, 2H), 7.54‐
7.63 (m, 2H), 7.78 (dd, J = 1.8 Hz, 2H), 7.90‐7.93 (m,
4H), 8.25 (s, 1H), 13C NMR (CDCl3, 75 MHz) ẟ 21.7,
125.9,126.7, 127.8, 128.1, 128.2, 129.1, 129.4, 130.4,
131.5, 132.4, 135.2, 135.3, 143.2, 196.5.
(3‐nitrophenyl)(phenyl)methanone
(2A21)[44]
:
1
Yellow solid, Yield = (64%, 36.3 mg), H NMR (CDCl3,
300 MHz) ẟ 7.53‐7.57 (m, 2H), 7.64‐7.74 (m, 2H),
7.79‐7.83 (m, 2H), 8.15 (td, J = 3.0 Hz, 1.2 Hz, 1H), 8.45
(qd, J = 2.4 Hz, 1.2 Hz, 1H), 8.62 (t, J = 1.8 Hz, 1H),
13C NMR (CDCl3, 75 MHz) ẟ 124.3, 126.3, 128.3, 129.2,
129.6, 133.0, 135.0, 135.9, 138.7, 147.7, 193.7.
(Naphthalen‐1‐yl)(p‐tolyl)methanone (2A29)[12e, 40]
:
1
White solid, Yield = (70%, 43.0 mg), H NMR (CDCl3,
300 MHz) ẟ 2.41 (s, 3H), 7.22‐7.25 (m, 2H), 7.44‐7.56 (m,
4H), 7.77 (d, J = 8.1 Hz, 2H), 7.90 (dd, J = 7.5 Hz, 2.4 Hz,
1H), 7.96‐7.98 (m, 1H), 8.02‐8.06 (m, 1H), 13C NMR
(CDCl3, 75 MHz) ẟ 21.8, 124.4, 125.7, 126.4, 127.1, 127.4,
128.4, 129.2, 130.6, 130.9, 131.0, 133.7, 135.7, 136.8,
144.2, 197.8.
(Naphthalen‐3‐yl)(phenyl) methanone (2A22)[12e]
:
White solid, Yield = (72%, 41.8 mg),1H NMR (CDCl3,
300 MHz) ẟ 7.41‐7.60 (m, 7H), 7.84‐7.92 (m, 3H), 7.97‐
7.99 (m, 1H), 8.07‐8.10 (m, 1H), 13C NMR (CDCl3,
75 MHz) ẟ 124.4, 125.7, 126.5, 127.3, 127.8, 128.4, 128.5,
130.4, 131.0, 131.3, 133.3, 133.7, 136.4, 138.3, 198.1.
(4‐methoxyphenyl)(thiophen‐2‐yl)methanone
(2A30)[27]: White solid, Yield = (77%, 41.9 mg),1H NMR
(CDCl3, 300 MHz) ẟ 3.89 (s, 3H), 6.99 (dd, J = 4.8 Hz,
2.1 Hz, 2H), 7.14‐7.17 (m, 1H), 7.64‐7.70 (m, 2H), 7.90
(dd, J = 4.8 Hz, 2.1 Hz, 2H); 13C NMR (CDCl3,
75 MHz) ẟ 55.5, 113.7, 127.8, 130.7, 131.6, 133.4, 134.0,
143.8, 163.1, 186.9.
4‐methoxy phenyl(p‐tolyl) methanone (2A23)[12e]
:
White solid, Yield = (72%, 40.7 mg and 69%, 39.0 mg), 1H
NMR (CDCl3, 300 MHz) ẟ 2.43 (s, 3H), 3.88 (s, 3H), 6.95
(dt, J = 4.8 Hz, 2.7 Hz, 2H), 7.26‐7.29 (m, 2H), 7.67 (dd,
J = 8.1 Hz, 1.8 Hz, 2H), 7.78‐7.82 (m, 2H), 13C NMR
(CDCl3, 75 MHz) ẟ 21.6, 55.5, 113.5, 128.9, 130.0, 130.5,
132.5, 135.5, 142.6, 163.0, 195.4.
4‐trifluoromethyl‐benzophenone (2A32)[41]: White
solid, Yield = (77%, 48.1 mg), 1H NMR (DMSO‐d6,
300 MHz) ẟ 7.56‐7.62 (m, 2H), 7.70‐7.80 (m, 3H), 7.93‐
7.96 (m, 4H), 13C NMR (DMSO‐d6, 75 MHz) ẟ 125.4,
125.5, 128.7, 129.8, 130.1, 133.3, 136.2, 140.7, 194.9.
(4‐fluorophenyl)(naphthalene‐4‐yl)methanone
(3‐nitrophenyl)(p‐tolyl)methanone
(2A24)[43]
:
Yellow solid, Yield = (67%, 40.3 mg and 78%, 47.0 mg),
1H NMR (CDCl3, 300 MHz) ẟ 2.47 (s, 3H), 7.32‐7.34 (m,
2H), 7.67‐7.73 (m, 3H), 8.12 (td, J = 2.7 Hz, 1.5 Hz,
1H), 8.43 (qd, J = 3.6 Hz, 1.2 Hz, 1H), 8.60 (t,
J = 1.8 Hz, 1H), 13C NMR (CDCl3, 75 MHz) ẟ 21.7,
124.6, 126.4, 129.4, 129.5, 130.2, 133.6, 135.3, 139.5,
144.4, 148.1, 193.8.
1
(2A33)[26]: White solid, Yield = (81%, 53.9 mg), H NMR
(DMSO‐d6, 300 MHz) ẟ 7.35‐7.41 (m, 2H), 7.55‐7.64 (m,
4H), 7.83‐7.92 (m, 3H), 8.06‐8.09 (m, 1H), 8.16‐8.19 (m,
1H), 13C NMR (DMSO‐d6, 75 MHz) ẟ 116.3, 116.5, 125.2,
125.4, 126.2, 127.1, 127.9, 128.6, 129.1, 130.5, 131.7,
133.3, 133.4, 133.7, 134.7, 134.7, 136.0, 164.0, 167.3, 196.2.
(Napthalen‐2‐yl)(napthalen‐5‐yl)methanone
(4‐fluorophenyl)(4‐methoxyphenyl)methanone
1
(2A25)[46]: White solid, Yield = (85%, 48.9 mg), H NMR
1
(DMSO‐d6, 300 MHz) ẟ 3.86 (s, 3H), 7.08‐7.11 (m, 2H),
7.38 (dt, J = 6.9 Hz, 1.8 Hz, 2H), 7.72‐7.79 (m, 2H); 13C
NMR (DMSO‐d6, 75 MHz) ẟ 56.0, 114.4, 115.8, 116.1,
129.7, 132.6, 132.7, 134.6, 134.7, 163.1, 163.4, 166.4, 193.5.
m‐tolyl(p‐tolyl) methanone (2A26)[47]: White solid,
(2A34)[50]: White solid, Yield = (71%, 50.0 mg), H NMR
(CDCl3, 300 MHz) ẟ 7.48‐7.54 (m, 4H), 7.57‐7.66
(m, 2H), 7.83 (d, J = 8.1 Hz, 1H), 7.89‐7.97 (m, 3H),
8.03‐8.13 (m, 3H), 8.24 (s, 1H), 13C NMR (CDCl3,
75 MHz) ẟ 124.4, 125.4, 125.7, 126.5, 126.8, 127.3, 127.7,
127.8, 128.4, 128.5, 128.7, 129.7, 131.0, 131.2, 132.4,
132.9, 133.8, 135.6, 135.7, 136.6, 198.0.
1
Yield = (79%, 41.5 mg), H NMR (CDCl3, 300 MHz) ẟ
2.41 (s, 3H), 2.43 (s, 3H), 7.25‐7.38 (m, 4H), 7.53‐7.60

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GHOSH ET AL.
Methyl‐4‐benzoylbenzoate (2A35)[51]: White solid,
δ 7.25 (t, J = 7.5 Hz, 2H), 7.53‐7.59 (m, 2H), 7.70‐7.75
(m, 2H), 8.23‐8.26 (m, 2H), 11.76 (s, 1H), 13C NMR
(75 MHz, DMSO‐d6) δ 117.3, 120.4, 121.0, 126.0, 133.4,
140.8, 176.8.
Yield = (56%, 33.6 mg),1H NMR (CDCl3, 300 MHz) ẟ
3.96 (s, 3H), 7.47‐7.52 (m, 2H), 7.59‐7.61 (m, 1H), 7.78‐
7.85 (m, 4H), 8.13‐8.16 (m, 2H), 13C NMR (CDCl3,
75 MHz) ẟ 52.5, 128.5, 129.5, 129.8, 130.2, 133.0, 133.2,
136.9, 141.3, 166.3, 196.0.
3‐chloroacridone‐9(10H)‐one (5b)[55]: Light yellow
solid, Yield = (76%, 43.7 mg), 1H NMR (300 MHz,
DMSO‐d6) δ 7.24‐7.31 (m, 2H), 7.51‐7.56 (m, 2H), 7.72‐
7.77 (m, 1H), 8.21 (d, J = 8.4 Hz, 2H), 13C NMR
(75 MHz, DMSO‐d6) δ 116.8, 118.0, 119.6, 121.1, 121.8,
122.1, 126.5, 128.9, 134.4, 138.5, 141.4, 142.1, 176.7.
(4‐cyano phenyl) (phenyl) methanone (2A36)[12e]
:
1
White solid, Yield = (32%, 17.0 mg), H NMR (CDCl3,
300 MHz) ẟ 7.49‐7.54 (m, 2H), 7.62‐7.64 (m, 1H), 7.71‐
7.81(m, 4H), 7.86‐7.89 (m, 2H), 13C NMR (CDCl3,
75 MHz) ẟ 115.7, 118.0, 128.6, 130.1, 130.2, 132.2, 133.3,
136.3, 141.2, 195.0.
2‐methylacridone‐9(10H)‐one (5c)[55]
:
Yellow
solid, Yield = (68%, 35.5 mg), 1H NMR (300 MHz,
DMSO‐d6) δ 2.43 (s, 3H), 7.23 (t, J = 7.8 Hz, 1H), 7.45‐
7.59 (m, 3H), 7.68‐7.73 (m, 1H), 8.03 (s, 1H), 8.22 (d,
J = 8.1 Hz, 1H), 11.66 (s, 1H), 13C NMR (75 MHz,
DMSO‐d6) δ 21.0, 117.6, 117.7, 120.8, 121.2, 125.5,
126.4, 130.5, 133.7, 135.4, 139.4, 141.2, 177.0.
di (p‐tolyl)methanone (2A37)[40b]: White solid,
1
Yield = (85%, 44.6 mg), H NMR (DMSO‐d6, 300 MHz)
ẟ 2.41 (s, 6H), 7.36 (d, J = 7.8 Hz, 4H), 7.63(d,
J = 8.1 Hz, 4H), 13C NMR (DMSO‐d6, 75 MHz) ẟ 21.6,
129.5, 130.1, 135.0, 143.3, 195.6.
bis (4‐chlorophenyl methanone) (2A38)[52]: White
solid, Yield = (88%, 55.2 mg),1H NMR (CDCl3,
300 MHz) ẟ 7.43‐7.51 (m, 4H), 7.69‐7.77 (m, 4H), 13C
NMR (CDCl3, 75 MHz) ẟ 128.7, 131.2, 135.4, 139.1, 194.2.
3‐iodo‐2‐phenylquinolin‐4(1H)‐one (3a)[53]: Light
Yellow solid, Yield = (70%, 60.7 mg), 1H NMR
(300 MHz, DMSO‐d6) ẟ 7.36‐7.42 (m, 1H), 7.53‐7.58 (m,
5H), 7.63‐7.69 (m, 2H), 8.13 (dd, J = 8.1 Hz, 0.9 Hz,
1H), 12.29 (s,1H); 13C NMR (75 MHz, DMSO‐d6) ẟ 86.3,
118.8, 121.3, 124.7, 125.9, 128.8, 129.4, 130.3, 132.6,
138.3, 139.7, 153.6, 174.1.
ACKNOWLEDGEMENTS
We thank the DST, New Delhi for financial support
(EMR/2016/001250). PG is thankful to UGC for his
fellowship.
ORCID
Sajal Das http://orcid.org/0000-0002-4225-5197
3‐benzoyl‐2‐phenyl‐quinolin‐4‐(1H)‐one (4a)[7]
:
1
White solid, Yield = (70%, 56.9 mg), H NMR (DMSO‐
d6, 300 MHz) ẟ 7.38‐7.48 (m, 8H), 7.56 (t, J = 7.5 Hz,
1H), 7.75‐7.79 (m, 4H), 8.10 (d, J = 8.1 Hz, 1H), 12.20
(s, 1H), 13C NMR (DMSO‐d6, 75 MHz) ẟ 119.3, 120.7,
124.5, 125.2, 125.3, 128.9, 129.0, 129.1, 129.4, 130.5,
132.9, 133.5, 134.0, 138.4, 140.3, 149.9, 175.5, 196.2.
3‐benzoyl‐(4‐chlorophenyl)‐quinolin‐4‐(1H)‐one
(4b)[7]: Pale yellow solid, Yield = (73%, 65.7 mg),1H NMR
(DMSO‐d6, 300 MHz) ẟ 7.41‐7.51 (m, 8H), 7.75‐7.81 (m,
4H), 8.10 (d, J = 8.1 Hz, 1H), 12.2 (s, 1H), 13C NMR
(DMSO‐d6, 75 MHz) ẟ 119.4, 120.2, 120.2, 124.5, 125.3,
129.0, 129.1, 129.2, 130.5, 131.3, 133.0, 134.0, 137.2,
138.3, 140.4, 150.5, 175.5, 195.1.
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one (4c)[7]: Brown solid, Yield = (62%, 52.5 mg), H
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J = 8.1 Hz, 2H), 7.42 − 7.44 (m, 6H),7.67 (d,
J = 8.1 Hz, 2H), 7.74‐7.76 (m, 2H), 8.10 (d, J = 8.0 Hz,
1H), 12.13 (s, 1H), 13C NMR (75 MHz, DMSO‐d6) δ
21.5, 119.2, 120.9, 124.4, 125.1, 125.3, 128.9, 129.0,
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Acridone‐9(10H)‐one (5a)[54]
:
Yellow solid,
1
Yield = (78%, 38.0 mg), H NMR (300 MHz, DMSO‐d6)

GHOSH ET AL.
11 of 12
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Das S. Pd‐NHC catalysed Carbonylative Suzuki
coupling reaction and its application towards the
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