Polystyrene-Supported Palladium (Pd?PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones

Article abstract of DOI:10.1002/chem.201902776

An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd?PS) nanoparticles (NPs) catalyzed con

Full text of DOI:10.1002/chem.201902776

A Journal of
Accepted Article
Title: Polystyrene supported palladium (Pd@PS) catalyzed
carbonylative annulation of aryl iodides using oxalic acid as a
sustainable CO source for the synthesis of 2-aryl quinazolinones
Authors: Shankar Ram, Shaifali --, Arvind Singh Chauhan, Sheetal --,
Ajay Kumar Sharma, and Pralay Das
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content of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.201902776
Link to VoR: http://dx.doi.org/10.1002/chem.201902776
Supported by

10.1002/chem.201902776
Chemistry - A European Journal
COMMUNICATION
Polystyrene
supported
palladium
(Pd@PS)
catalyzed
carbonylative annulation of aryl iodides using oxalic acid as a
sustainable CO source for the synthesis of 2-aryl quinazolinones
Shankar Ram,[a,b] Shaifali,[a,b] Arvind Singh Chauhan,[a,b] Sheetal,[a,b] Ajay Kumar Sharma[a,b] and Dr.
Pralay Das[a,b] *
Abstract: An efficient and convenient strategy for the synthesis of
diversely substituted quinazolinones from o-carbamoyl/cyano aniline
and aryl iodides using oxalic acid as a CO source under polystyrene
supported palladium (Pd@PS) nanoparticles (NPs) catalyzed
conditions has been developed. Under this study, we have employed
oxalic acid as safe, economic, environmentally benign, sustainable
and bench stable solid CO surrogate under Double-Layer-Vial (DLV)
system for the synthesis of 2-aryl quinazolinones. This methodology
does not require any special high-pressure equipment like autoclave,
microwave etc. Moreover, simple procedure for catalyst preparation,
catalyst recyclability, easy handling of reaction, additive and base
free generation of CO, excellent to good yields and vast substrate
scope are the additional features of developed protocol.
reports available on the carbonylative synthesis of
quinazolinones using carbon monoxide gas as C1 source. Zhu
and co-workers reported an interesting palladium catalyzed
intramolecular oxidative carbonylation of N-arylamidines to
synthesize quinazolinones.[16] The reactions were carried out in
the presence of palladium acetate together with one equivalent
of CuO under one bar of CO gas. Later on, palladium catalyzed
carbonylative coupling for the synthesis of 2-arylbenzoxazinones
and its application for one pot synthesis of 2-arylquinazolinones
was demonstrated by Beller and co-workers.[17a] In 2013, Wu et
al. reported Pd-catalyzed carbonylative annulations of o-
aminobenzamides with aryl bromides for the synthesis of
quinazolinones using CO gas as C1 source.[17b] However, in
case of aryl iodides they got only 30% yield of the desired
product. Later, Wu and co-workers reported palladium(II)-
catalyzed cascade synthesis of quinazolinone from o-
aminobenzonitrile, CO and aryl bromide.[18] More recently, You
et al. demonstrated carbonylative annulation reactions to
synthesize quinazolinones using CO gas as C1 source under
MCM-41-immobilized bidentate phosphine palladium(II) complex
catalyzed conditions.[19] Most of these carbonylative annulation
strategies for the synthesis of quinazolinones required high
pressurized CO gas as C1 source.
2-Aryl quinazolinone and its derivatives constitute an
important class of nitrogen containing fused heterocycles
existing in
a variety of natural products and bioactive
molecules.[1] These are also privileged structures for the
development of drug candidates[2] due to their broad spectrum of
biological and medicinal applications such as antiviral,[3]
antimicrobial,[4] antimalarial,[5] anticancer,[6] anticonvulsant[7] etc.
Furthermore, they are also used as ligand for benzodiazepine
and
α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic
acid
(AMPA) receptors in the central nervous system (CNS) for
acquired epilepsy treatment or as DNA binders.[7a,8] Owing to
broad applications of quinazolinones, various synthetic methods
have been developed for their synthesis.[9] The traditional
approach to obtain quinazolinones rely on the condensation of
o-aminobenzamides with aldehydes,[10] benzyl alcohol,[11] aryl
ketones,[12] benzyl amines,[13] and carboxylic acid[14] etc.
However, most of these methods generally require some excess
amount of oxidants, homogeneous catalytic system and
additives.
During the last few decades, palladium catalyzed
carbonylative transformation of organo-halides has become a
powerful tool in the modern organic synthesis.[15] There are few
[a]
Shankar Ram, Shaifali, Arvind Singh Chauhan, Sheetal, Ajay
Kumar Sharma and Dr. Pralay Das
Scheme1. Palladium catalyzed carbonylative synthesis of quinazolinones.
Natural Product Chemistry & Process Development Division,
CSIR-Institute of Himalayan BioresourceTechnology, Palampur
176061, HP, India
However, in most of the general lab practices the use of CO
gas-based carbonylation reactions have been avoided because
expensive high-pressure equipment is needed to perform such
reactions and safety issues associated with this odorless, toxic
and flammable gas as well. Therefore, owing to the limitation of
E-mail: pdas@ihbt.res.in;
[b]
Academy of Scientific & Innovative Research, CSIR-IHBT,
Palampur-176061, H.P, India.
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CO gas based carbonylation reactions, utilization of non-toxic,
sustainable, economic and bench stable solid CO surrogate is
desirable for the synthesis of quinazolinones. Furthermore, the
screened catalysts, Pd@PS was found to be most effective in
our standard reaction conditions for the
Table 1: Optimization of the reaction parametersa
application
of
homogeneous
palladium
complex
in
pharmaceutical industries remains a big challenge, as they are
costly, non-recyclable and very difficult to separate from the
reaction mixture.
In this context, for last few years our group have been
continuously working on the development of polystyrene
supported (PS) transition metal nanoparticles (NPs) as
heterogeneous catalyst and their applications in different
carbonylation and carboxylation reaction by utilizing oxalic acid
as safe, sustainable and bench stable CO building block.[20]
Recently, our group demonstrated Pd@PS catalyzed
aminocarbonylation of aryl halides with amines using oxalic acid
as ex situ CO surrogate under DLV(Double Layer Vial) system
and their single-pot application in isoindolinone synthesis.[21] In
continuation of our earlier development, herein, we report an
efficient and convenient synthesis of 2-aryl quinazolinones from
o-carbamoyl/cyano aniline and aryl iodides under Pd@PS
catalyzed conditions using oxalic acid as bench stable solid CO
surrogate.
The nano-catalyst Pd@PS was prepared by following our
previously reported reduction deposition method (Supporting
Information) and fully characterized by X-ray diffraction (XRD),
scanning electron microscopy (SEM), transmission electron
microscopy (TEM),
high resolution transmission electron
microscopy (HRTEM), energy dispersive spectroscopy (EDS)
and selected area electron diffraction (SAED) studies.[20a, 22] In
this study, the developed nano-catalyst Pd@PS was further
applied to the carbonylative cyclization reaction for the synthesis
of 2-aryl quinazolinones.
In a pursuit to develop convenient and efficient approach for
the synthesis of quinazolinone, we began our investigation with
a model reaction: 2-aminobenzamide (1 equiv.), iodobenzene
(1.5 equiv.), Pd@PS (3 mol%), oxalic acid dihydrate (6 equiv.),
DBU (2 equiv.) in DMF (2.0 mL) at 130 oC for 24 hrs. The
targeted product 2-phenylquinazolinone (3a) formed in 30%
isolated yield (Table1, entry1). In order to get optimum yield of
the targeted product (3a), we further screened several reaction
parameters such as catalyst concentration, C1 source, base,
solvent, temperature and reaction time (Table1). We have
evaluated different bases and solvents (Table1, entries 2-9),
among them K2CO3 (2 equiv.) in DMF solvent was found to be
the optimal base as the yield increased from 30 to 91% (Table1,
entry 9). Decreasing the amount of base afforded the desired
product 3a in lower yield (Table1, entry 10). Further, replacing
the oxalic acid with N-formyl saccharin and formic acid gave the
desired product 3a in 17% and 10% isolated yields respectively
(Table 1, entries 12-13). These results revealed that oxalic acid
was best CO surrogate among others as it decomposed easily
to release CO and also compatible with the Pd@PS catalyst. We
also screened different homogeneous and heterogeneous
palladium catalysts such as Pd(OAc)2, Pd(OAc)2 with ligand
(dppb), Pd2(dba)3, Pd(PPh3)4 PdCl2(PPh3)2, Pd/C (5 wt%) and
results summarized in Table1 (Entries 14-19). Among the
aReaction conditions: inner vial - o-aminobenzamide (0.36 mmol), aryl iodide
(0.54 mmol), Pd@PS (3 mol%), K2CO3 (0.72 mmol), DMF (1.5 mL); outer vial -
oxalic acid dihydrate (2.16 mmol), DMF (0.5 mL), 130 oC, 24 hrs; b Isolated
c
d
e
yields; Reaction temperature was 120 oC; 4 equiv. oxalic acid was used;
Reaction time was 15 hrs. * Conversion = 100%.
selective synthesis of 2-phenylquinazolinone 3a. This may be
due to the good holding capacity of the oxalic acid over surface
through ionic bonding and their simultaneous decomposition to
produce CO and further adsorption inside the hydrophobic
pocket of polymer matrix and the close vicinity of CO with Pd-
catalyst on the same surface may enhance the availability of CO
for the reaction to produce corresponding product, as also
described in our previous reports.[20,21] We also tested the effect
of temperature during the course of reaction and found that 130
oC was the optimal temperature. In the absence of Pd@PS
catalyst, no desired product (3a) formation was noticed (Table 1,
entry 20). The reaction also did not occur when oxalic acid
dihydrate removed from the outer vial, which concluded that CO
was coming from oxalic acid (Table 1, entry 21). On decreasing
o
the reaction temperature (120 C), reaction time (15 h), catalyst
concentration (2 mol%) and proportion of oxalic acid dihydrate (4
equiv.), resulted in lower yields of desired product 3a (Table 1,
entries 11, and 22-24).
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Table 2. Substrate scopes for 2-aryl quinazolinones synthesis from
o-aminobenzamides and aryl iodides.a
aReaction conditions: inner vial - o-aminobenzamide (0.36 mmol), aryl iodide
(0.54 mmol, 1.5 equiv.), Pd@PS (3 mol%), K2CO3 (0.72 mmol, 2 equiv.), DMF
(1.5 mL); outer vial-oxalic acid dihydrate (2.16 mmol, 6 equiv.), DMF (0.5 mL),
130 oC, 24 hrs; b Isolated yields.
To explore the scope and generality of the developed
protocol, we started the investigation of substrates for this
transformation and a variety of o-aminobenzamides as well as
aryl iodides were studied and results summarized in Table 2.
Initially, we screened aryl iodides with o-aminobenzamide as a
reaction partner under optimized reaction conditions. Excellent
to good yields of target products were obtained with aryl iodides
containing electron-donating groups. Aryl iodides having methyl
or methoxy group at meta or para positions produced the
desired products 3b-e in 70-84% yields. Sterically hindered o-
iodotoluene provided the corresponding product 3f in 60%
isolated yield. Para-fluoro and chloro substituted aryl iodides
were well tolerated under the reaction conditions and procured
the desired products 3g-h in 82 and 70% yields respectively.
Aryl iodides having electron withdrawing functionality are the
challenging substrates for the carbonylative coupling reactions.
In this context, some interesting aryl halides having electron
withdrawing substituents such as 4-COCH3, 4-COOCH3, 4-CF3,
4-CHO also applied under optimized reaction conditions. To our
delight, these aryl halides found to be reactive under the
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reaction conditions and provided the desired product 3i-3l in 62-
73% isolated yields. 2-Iodothiophene as well as 1-
iodonaphthalene also successfully delivered the desired product
3m-n in 67 and 52% yields respectively.
increased from 40 to 64%. Notably, in this case we did not get
benzoic acid which could be a side product of reaction. Next, we
moved towards the scope and generality of this transformation
by employing different o-aminobenzonitriles and aryl iodides
under set reaction conditions (Table 3). A variety of substituents
such as -CH3, -F, -Br were well tolerated and furnished
corresponding quinazolinones 4b-e in 53-68% yields. However,
in case of 4-Me and 4-F iodobenzene, we got respective benzoic
acid derivatives in traces as side product. Interestingly, 4-
The optimized reaction condition was also applied to a series
of o-aminobenzamides with aryl iodides. The o-aminobenzamide
bearing electron donating substituents participated well in the
reaction and provided the desired products 3o-p and 3r in 78-
80% isolated yields. However, under the present condition p-
iodoanisole with 5-methyl-2-aminobenzamide gave the desired
product 3q in 55% isolated yield. The fluoro, chloro and bromo
substituted o-aminobenzamides regardless of their electronic
properties and respective position of substituents, underwent
carbonylative annulation reaction with aryl iodides efficiently to
produce corresponding 2-aryl quinazolinones 3s-y in 65-85%
trifluoromethyl-2-aminobenzonitrile
with
iodobenzene
successfully delivered the desired product 4f in 86% yield.
The recyclability experiments of polystyrene supported
palladium (Pd@PS) nanoparticles (NPs) were carried out with o-
aminobenzamide and iodobenzene under standard reaction
conditions. After the completion of the reaction, the reaction
mixture was quenched with water and the organic layer was
extracted with ethyl acetate. Further the catalyst was filtered out
and washed with water and acetone, then dried and reused for
another reaction. The catalyst was found to be recycled upto five
cycles with some loss in catalytic activity (Figure1). Very similar
reason for loss in catalytic activity was noticed as mentioned in
our earlier reports.[20c,20d]
isolated yields. Interestingly, 5-bromo substituted
o-
aminobenzamide well tolerated under the reaction conditions
and gave the desired product 3v in good yield. Notably,
trifluoromethyl (4-CF3) substituted 2-aminobenzamide also
reacted well, affording the desired product 3z in 75% yield.
Unfortunately, very poor yield (10%) of desired product obtained
when reaction of o-aminobenzamide carried out with
bromobenzene, whereas reaction did not occur with
chlorobenzene under the standard reaction conditions.
Table 3. Carbonylative annulations reaction of o-aminobenzonitrile and aryl
iodides using oxalic acid as CO source for the synthesis of quinazolinones.a
Figure1. Recyclability experiments of Pd@PS catalyst.
In summary, we have developed an operationally simple and
efficient method for the synthesis of 2-aryl quinazolinones from
o-aminobenzamides and aryl iodides, through Pd@PS NPs
catalyzed carbonylative annulation reaction using oxalic acid
dihydrate as cheap and bench stable CO surrogate. Following
this method, a series of 2-aryl quinazolinones with electron
sufficient or deficient substrates were performed with excellent
to good yields. The developed methodology was also applied to
different o-aminobenzonitriles and gave a variety of 2-aryl
quinazolinones under single-pot reaction in considerably good
yields. The catalyst can easily be prepared by simple procedure
and recyclable up to 5 times with some loss in catalytic activity.
Oxalic acid as bench stable solid CO surrogate in combination
with the simple Double-Layer-Vial (DLV) reaction system could
enhance the applicability of the reaction for general lab practices.
aReaction conditions: inner vial- o-aminobenzonitrile (0.42 mmol), aryl iodide
(0.63 mmol, 1.5 equiv.), Pd@PS (3 mol%), K2CO3 (1.26 mmol, 3 equiv.), DMF
(1.2 mL), H2O (0.3 mL); outer vial - oxalic acid dihydrate (2.52 mmol, 6 equiv.),
DMF (0.5 mL), 130 oC, 30 hrs. # Benzoic acid of aryl halide was detected in
traces.
During the substrates investigation, when we applied 2-iodo
benzonitrile with o-aminobenzamides for carbonylative
annulation reaction, no desired product formed but a small
amount of benzamide formation was noticed. This may be due
to the presence of water in the reaction mixture formed during
the decomposition of oxalic acid dihydrate. Encouraged by these
observations, we carried out a reaction of o-aminobenzonitrile
with iodobenzene taking DMF:H2O (4:1) as solvent system
under the identical catalytic conditions and produced the desired
product (2-aryl quinazolinones) in 40% isolated yield. After
increasing the equivalency of base 2 to 3 equivalent and
reaction time 24 to 30 h, yield of the desired product 4a was
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Experimental Section
Typical procedure for the synthesis of 2-phenylquinazolinone (3a):
With a double layer vial system (DLV), 2-aminobenzamide (0.36 mmol,
50 mg), iodobenzene (0.55 mmol, 112.5 mg), Pd@PS (0.01 mmol, 246
mg), K2CO3 (0.73 mmol, 101 mg) and DMF (1.5 mL) was added in 2 mL
vial (inner vial) and this vial was placed inside 5 mL reaction vessel
(outer vial) containing oxalic acid dihydrate (2.20 mmol, 277 mg) and 0.5
mL of DMF. The 5 mL reaction vessel was tightened with solid PTFE cap
and stirred at 130 oC for required time. The progress of reaction was
monitored with the help of TLC. After the completion of reaction, the inner
vial was taken out and reaction mixture was quenched with the help of
water, organic layer was extracted with ethyl acetate. The extracted
organic layer was dried over sodium sulphate and concentrated over
rotary evaporator. The crude mixture was further purified by column
chromatography using hexane:ethyl acetate (80:20) as elutent, afforded
compound 3a as white solid (74 mg); yield: 91%; m.p: 248-250 oC.1H
(600 MHz, DMSO-d6) δ (ppm) = 7.49-7.59 (m, 4H), 7.73-7.75 (m, 1H),
7.81-7.86 (m, 1H), 8.15-8.20 (m, 3H), 12.5 (brs, 1H).13C (150 MHz,
DMSO-d6) δ (ppm) = 121.45, 126.30, 127.02, 127.96, 128.22, 129.04,
131.33, 133.18, 135.04, 149.20, 152.76, 162.68.The expected ESI-
MS(M+H)+ for C14H11N2O+ is 223.0866 and observed 223.0872.
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We are grateful to the Director, CSIR-IHBT for providing
necessary facilities during the course of the work. S. Ram,
Shaifali, A.S.Chauhan, Sheetal and A.K. Sharma thanks CSIR
and UGC and DST-INSPIRE, New Delhi for awarding
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Keywords: palladium nanoparticles (NPs)
•
oxalic acid
dihydrate • o-aminonenzamides • o-aminobenzonitriles • 2-aryl
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Shankar Ram,[a,b] Shaifali,[a,b] Arvind
Singh Chauhan,[a,b] Sheetal,[a,b] Ajay
Kumar Sharma[a,b] and Dr. Pralay
Das[a,b]*
Page No. – Page No.
Polystyrene supported palladium
(Pd@PS) catalyzed carbonylative
annulation of aryl iodides using
oxalic acid as
a sustainable CO
source for synthesis of 2-aryl
quinazolinones
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