A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles

Article abstract of DOI:10.1007/s12039-012-0343-0

One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO₃)₂.3H ₂O catalyst at room/ambient temperature in excellent yield.

Full text of DOI:10.1007/s12039-012-0343-0

c
J. Chem. Sci. Vol. 125, No. 1, January 2013, pp. 175–182. ꢀ Indian Academy of Sciences.
A Cu (NO3)2.3H2O catalysed facile synthesis of substituted
4(3H)-quinazolinones and benzimidazoles
G A N K DURGAREDDYb, R RAVIKUMARa,∗, S RAVIb and SRINIVAS R ADAPAc
aDepartment of Chemistry, School of Chemical and Biotechnology, SASTRA University,
Thanjavur 613 401, India
bDepartment of Chemistry, Karpagam University, Coimbatore 641 021, India
cIndian Institute of Chemical Technology, Hyderabad 501 607, India
e-mail: rravikumar@chem.sastra.edu
MS received 31 March 2012; revised 2 June 2012; accepted 28 June 2012
Abstract. One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl
or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H2O
catalyst at room/ambient temperature in excellent yield.
Keywords. Quinazolinones; benzimidazoles; Cu (NO3)2.3H2O.
1. Introduction
are the condensation of orthophenylenediamines and
carboxylic acids (or its derivatives like nitriles, imidates
and orthoesters) under vigorous dehydrating condi-
tions,38 rhodium catalysed hydroformylation reaction
of N-alkenyl phenylenediamines,39 reductive cycli-
sation reaction of o-nitroaniline with aldehydes,40
palladium catalysed tandem carbonylation–cyclisation
reaction of o-phenylenediamine,31 palladium catal-
ysed tandem dehydration-coupling reaction of 2-
bromoaniline,41 and solid phase supported synthesis.42
Most of the methods suggested having limitations such
as low yield, tedious work-up procedures, by-product
formation, long reaction time, expensive reagents and
lack of selectivity. In addition to that, some methods
do not satisfy the requirements such as operational
simplicity, economic viability, greater selectivity, ease
of recovery of the products from the reaction mix-
ture. However, condensation–aromatization reaction of
orthophenylenediamine and aldehydes under oxidative
conditions turned out to be the effective method to syn-
thesize mono and di substituted benzimidazoles.43,44
We have explored the catalytic efficiency of L- pro-
line45 in chloroform and Zn-proline complex46 in water
towards the synthesis of 1,2-disubstituted benzimida-
zoles at ambient temperature.
Diverse pharmacological activities of the two heterocy-
cles, quinazolinone and benzimidazole derivatives have
been well-established through a number of research
articles. Quinazoline-4(3H)-ones possess pharmacologi-
cal activities1–11 such as analgesic, antibacterial, anti-
convulsant, antidiabetic, antitumour, phosphorylation
inhibition and CNS depressant activity. Similarly, broad
spectrum pharmacological activities of benzimidazole
core, classified by medicinal chemists as a ‘privileged
sub-structure’ for drug design, possess affinity towards
a variety of enzymes and protein receptors.12 Benzimi-
dazole containing structures exhibit significant activity
against viruses such as HIV, herpes (HSV-1), influenza
and human cytomegalovirus (HCMV).13–17 Benzimi-
dazole derivatives can also be used as topoisomerase
inhibitors, selective neuropeptide YY1 receptor antag-
onists, angiotension II inhibitors, 5-HT3 antagonists in
isolated guinea pig ileum, smooth muscle cell prolife-
ration inhibitors, potential antitumour agents, antimi-
crobial agents and in diverse area of chemistry.18–23 In
addition, the treatment potency of benzimidazoles in
diseases such as ischemia-reperfusion injury, hyperten-
sion and obesity have been reported recently.24–26
Several synthetic routes have been suggested for both
1,2 disubstituted-1H-benzimidazole27–33 and 4(3H)-
quinazolinone34–37 derivatives. Widely used synthetic
strategies for the preparation of 1H-1,2-benzimidazoles
2. Experimental
All reagents and solvents available commercially were
used without further purification. Reactions were fol-
lowed by TLC analysis. Melting points were observed
∗For correspondence
175

176
G A N K Durgareddy et al.
Table 1. Synthesis of 1,2 disubstituted-1H-benzimidazoles by the reaction of aliphatic, aromatic and hetero aromatic
aldehydes with orthophenylenediamine, catalysed by Cu(NO3)2.3H2O in CH3CN at room temperature.
Entry
Aldehyde
Product
Stirring time (h)
5
Yield(%)*
92
N
N
1a
Benzaldehyde
N
N
1b
1c
4-Chlorobenzaldehyde
4-Methoxybenzaldehyde
8
5
75
82
Cl
Cl
N
N
OCH3
H3CO
N
N
1d
1e
1f
4-Nitrobenzaldehyde
8
5
5
70
75
70
NO2
O2N
N
2-Hydroxybenzaldehyde
4-Hydroxybenzaldehyde
N
HO
OH
N
N
OH
HO
CH3
N
N
1g
1h
4-N,N-dimethyl amino benzaldehyde
3-Methoxy -4-hydroxy benzaldehyde
6
6
78
72
N
CH3
H3C
N
CH3
OCH3
OH
N
N
HO
OCH3
N
1i
1j
Pyridine-2-carboxaldehyde
10
5
75
80
N
N
N
N
O
2-Furfural
N
O

4(3H)-quinazolinones and benzimidazoles
177
Table 1. (continued).
Entry
Aldehyde
Product
Stirring time (h)
5
Yield(%)*
80
1k
Propanaldehyde
N
N
1l
n-Butyraldehyde
5
77
N
N
*Isolated yield.
using open capillaries in a sulphuric acid bath. IR and
1b. IR spectrum,ν, cm−1: 2923, 2851, 1448, 1428,
1
1H NMR spectra in CDCl3/DMSO-d6 as a solvent 1275, 744. H NMR spectrum (300 MHz, CDCl3), δ,
were recorded on Perkin-Elmer and Varian 300 MHz ppm (J, Hz): 5.39 (s, 2H), 7.59–7.61 (m, 2H), 7.60
spectrometer, respectively.
(d, 2H, J = 8.6 Hz), 7.19 (d, 1H J = 7.7 Hz), 7.24–7.38
(m, 4H), 7.40–7.45 (m, 2H), 7.84 (d, 1H, J = 7.7 Hz).
2.1 General procedure for synthesis of
benzimidazoles and quinazolinones
1c. IR spectrum,ν, cm−1: 3053, 2963, 2935, 1459,
1294, 1382, 1459. 1H NMR spectrum (300 MHz,
CDCl3), δ, ppm (J, Hz):3.77 (s,3H), 3.83 (s, 3H), 5.45
(s, 2H), 6.81 (d, 2H, J = 8 Hz), 6.99 (m, 4H), 7.22
(m, 3H), 7.64 (d, 2H, J = 9 Hz), 7.78 (d, 1H, J = 8 Hz).
2.1a Benzimidazoles: A mixture of orthophenylene-
diamine (1 mmol), Cu(NO3)2.3H2O (20 mmol) and the
appropriate aldehyde (2.3 mmol) in CH3CN (10 mL)
was stirred at room temperature for the time speci-
fied in table 1. Completion of the reaction was moni-
tored by TLC. The product was washed with water
and extracted with solvent ether. The product was puri-
fied by silica gel packed column chromatography eluted
with ethylacetate/n-hexane (3:7) solvent system.
1d. IR spectrum,ν, cm−1: 3046, 2965, 1463, 1326,
1
1479. H NMR spectrum (300 MHz, CDCl3), δ, ppm
(J, Hz): 5.74 (s, 2H),7.19 (dd, 1H, J = 8 Hz), 7.23–
7.32 (d, 2H, J = 9 Hz), 7.35 (td, 1H, J = 9 Hz), 7.54
(td, 1H, J = 7 Hz), 7.79 (d, 2H, J = 9 Hz), 7.91–7.98
(dd, 1H, J = 8 Hz), 8.15–8.2 (d, 2H, J = 8 Hz), 8.34
(d, 2H, J = 9 Hz).
2.1b Quinazolinones: A mixture of anthranilamide
(1 mmol), Cu(NO3)2.3H2O (20 mmol) and the appro-
priate aldehyde (1.3 mmol) in CH3CN (10 mL) was
heated at 80◦C for the time specified in table 2. Comple-
tion of the reaction was monitored by TLC. The product
was washed with water and extracted with ethyl acetate.
The product was purified by silica gel packed col-
umn chromatography eluted with ethylacetate/n-hexane
(3:7) solvent system.
1e. IR spectrum,ν, cm−1: 3288, 3048, 2926, 1394,
1
1240, 1454, 1592. H NMR spectrum, (300 MHz,
CDCl3 + DMSO), δ, ppm (J, Hz): 5.57 (s, 2H), 6.85–
7.01 (m, 4H), 7.19–7.36 (m, 5H), 7.70–7.80 (m, 2H),
7.92 (d, 1H, J = 7.6 Hz), 2.52 (br s, 2H).
1f. IR spectrum,ν, cm−1: 3246, 2923, 1515, 1443,
1246, 1347. 1H NMR spectrum, (300 MHz, DMSO), δ,
ppm (J, Hz): 5.35 (s,2H), 6.80–6.91 (m, 4H), 7.11–7.46
(m, 6H), 7.91 (d, 2H, J = 7.6 Hz), 10.86 (br.s, 2H).
2.2 Spectral data of the compounds
1a. IR spectrum,ν, cm−1: 3030, 2926, 1468, 1328,
1444. 1H NMR spectrum (300 MHz, CDCl3), δ, ppm (J,
Hz): 5.45 (s, 2H,), 7.12 (dd, 2H, J = 8.2 Hz), 7.15–7.38
(m, 6H), 7.4–7.48 (m, 3H), 7.70 (dd, 2H, J = 8.2 Hz),
7.85 (d, 1H, J = 8 Hz).
1g. IR spectrum,ν, cm−1: 2880, 2800, 1441, 1250,
1
1526. H NMR spectrum (300 MHz, CDCl3), δ, ppm

178
G A N K Durgareddy et al.
Table 2. Synthesis of mono(2)-substituted 4(3H)-quinazolinones by the reaction of aliphatic, aromatic and hetero aromatic
aldehydes with anthranilamide, catalysed by Cu(NO3)2.3H2O in CH3CN at 80◦C.
Entry
Aldehyde
Product
Heating time (h)
9
Yield (%)*
93
O
2a
Benzaldehyde
NH
N
O
2b
2c
2d
2e
4-Methoxybenzaldehyde
9.5
10
10
10
88
80
75
78
NH
NH
N
OCH3
O
N
3-Methoxy-4-hydroxy benzaldehyde
4-Hydroxybenzaldehyde
OCH3
OH
O
NH
N
OH
O
4-N,N-dimethylamino benzaldehyde
NH
N
CH3
N
CH3
2f
2-Hydroxybenzaldehyde
4-Chlorobenzaldehyde
4-Nitrobenzaldehyde
2-Furfural
11
10
12
10
84
79
78
77
O
N
NH
OH
O
2g
2h
2i
NH
N
Cl
O
NH
N
NO2
O
N
NH
O

4(3H)-quinazolinones and benzimidazoles
179
Table 2. (continued).
Entry
Aldehyde
Product
Heating time (h)
10
Yield (%)*
80
2j
Propanaldehyde
O
NH
N
2k
n-Butyraldehyde
10
77
O
NH
N
*Isolated yield.
(J, Hz): 2.93 (s, 6H), 3.01(s, 6H), 5.37 (s, 2H), 6.66– J = 4.7 Hz), 1.5–1.9 (m, 6H), 2.1 (t, 2H, J = 4.9 Hz),
6.75 (m, 4H), 6.95–7.02 (m, 2H), 7.14–7.29 (m, 2H), 5.1 (t, 2H, J = 5.6 Hz), 7.1 (m, 4H).
7.63 (d, 2H, J = 8.8 Hz), 7.79 (m, 2H).
2a. IR spectrum,ν, cm−1: 1673, 1456, 1175,1342,
1030, 955, 730. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz): 7.56–7.62 (m, 4H), 7.75–7.84 (m,2H),
8.18–8.53 (m,3H), 12.46 (s, 1H).
1h. IR spectrum,ν, cm−1: 3399, 2998, 2935, 2832,
1458, 1274, 1389, 1458. 1H NMR spectrum (300 MHz,
CDCl3), δ, ppm (J, Hz): 3.70 (s, 3H), 3.81 (s, 3H), 5.39
(s, 2H), 6.49 (d, 1H, J = 7.9 Hz), 6.60 (d, 1H, J =
8.1 Hz), 6.90 (d, 2H, J = 8.4 Hz), 7.10–7.30 (m, 5H),
7.69 (d, 1H, J = 8.6 Hz), 8.40 (s, 1H), 8.95 (s, 1H).
2b. IR spectrum,ν, cm−1: 1675, 1585, 1485, 1295,
1011, 870, 780. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz): 3.85 (s, 3H), 6.93–7.73 (m, 4H), 7.81 (d,
2H, J = 7.1 Hz), 8.13 (d, 2H, J = 7.3 Hz), 12.47 (s, 1H).
1i. IR spectrum,ν, cm−1: 3041, 2924, 2855, 1482,
1
1276, 1423. H NMR spectrum (300 MHz, CDCl3),
δ, ppm (J, Hz): 5.50 (s, 2H), 7.19–7.42 (m, 3H), 7.85
(d, 1H, J = 7.3 Hz), 7.98 (d, 1H, J = 7.8 Hz), 8.59
(d, 2H, J = 7.9 Hz), 8.58–8.62 (m, 3H), 8.72 (d, 1H,
J = 8.1 Hz), 8.85 (s, 1H).
2c. IR spectrum,ν, cm−1: 1668, 1578, 1493, 1288,
1143, 1027, 860, 770. H NMR spectrum (300 MHz,
DMSO), δ, ppm (J, Hz):3.90 (s, 3H), 6.93–7.52
(m, 4H), 7.71 (d, 1H, J = 7.5 Hz) 7.75 (s, 1H) 7.82
(d, 1H, J = 7.2 Hz) 8.82 (s, 1H), 12.42 (s,1H).
1
1j. IR spectrum,ν, cm−1: 3114, 2926, 1506, 1254,
1216, 1452. 1H NMR spectrum (300 MHz, CDCl3), δ,
ppm (J, Hz): 5.69 (s, 2H), 6.20 (d, 1H, J = 7.8 Hz),
6.30 (d, 1H, J = 7.6 Hz), 6.61–6.79 (m, 1H), 7.23–7.41
(m, 4H), 7.34 (d, 1H, J = 7.4 Hz), 7.67–7.80 (m, 2H).
2d. IR spectrum,ν, cm−1: 1665, 1604, 1520, 1350,
1315, 960, 765. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz): 6.91 (m, 4H), 7.48 (d, 2H, J = 7.8 Hz),
7.68 (d, 2H, J = 7.7 Hz), 9.24 (s, 1H), 12.02 (s, 1H).
1k. IR spectrum,ν, cm−1: 3104, 2906, 1526, 1224,
1442, 951. H NMR spectrum (300 MHz, CDCl3), δ,
ppm (J, Hz): 0.56 (t, 3H, J = 4.7 Hz), 1.09 (t, 3H, J =
4.1 Hz), 1.29 (m, 2H), 2.3 (q, 2H, J = 3.9 Hz), 4.7
(t, 2H, J = 4.3 Hz), 7.3 (d, 1H, J = 7.6 Hz), 7.6 (m, 3H).
2e. IR spectrum,ν, cm−1: 1668, 1601, 1524, 1450,
1295, 961, 764. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz): 3.04(s, 6H), 6.84 (m, 4H,), 7.44 (d, 2H,
J = 7 Hz), 7.81 (d, 2H, J = 7.2 Hz), 12.04 (s, 1H).
1
2f. IR spectrum,ν, cm−1: 1663, 1553, 1457, 1288,
1l. IR spectrum,ν, cm−1: 3012, 2917, 1496, 1184,
1
1248, 948, 753 cm−1. H NMR spectrum (300 MHz,
1
1402, 935. H NMR spectrum (300 MHz, CDCl3), δ,
DMSO), δ, ppm (J, Hz): δ 6.73 (m, 4H), 7.49 (m, 4H),
ppm (J, Hz): 0.81 (t, 3H, J = 4.2 Hz), 1.1 (t, 3H,
9.24 (s, 1H), 12.34 (s, 1H).

180
G A N K Durgareddy et al.
2g. IR spectrum,ν, cm−1: 1679, 1609, 1490, 1160, 3. Results and discussion
1020, 950,735. 1H NMR spectrum (300 MHz, DMSO),
In our attempt to find a water soluble, economical
δ, ppm (J, Hz): 7.52 (m, 4H), 7.76 (d, 2H, J = 6.6 Hz),
catalyst with activity at room temperature/ambient
temperature, having good selectivity and yield. The
efficiency of Cu(NO3)2.3H2O as a catalyst to syn-
thesize 1,2 disubstituted benzimidazoles as well as
mono(2)substituted 4(3H)-quinazolinones is reported
here. Variety of catalytic substances like AlCl3, FeSO4,
Cu(OAC)2, AgNO3, Nd(NO3)2.6H2O, Zn(NO3)2.
6H2O, Ni(NO3)2.6H2O, CoCl2, Ru(acac)2, Ba(NO3)2,
Al(NO3)3, ZnCl2, CuSO4.5H2O in combination with
different solvents such as DCM, DMF, THF, MIBK
(methyl isobutyl ketone) were analysed for their cata-
lytic activity. No reaction or very low yield (<10%)
was observed.
7.79 (d, 2H, J = 7.1 Hz), 11.80 (s, 1H).
2h. IR spectrum,ν, cm−1: 1665, 1604, 1520, 1350,
948, 765, 638. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz): 7.43 (m, 4H) 7.48 (d, 2H, J = 7.6 Hz),
7.68 (d, 2H, J = 7.4 Hz), 12.02 (s, 1H).
2i. IR spectrum,ν, cm−1: 1662, 1602, 1572, 1465,
1355, 1109, 707. 1H NMR spectrum (300 MHz,
DMSO), δ, ppm (J, Hz):7.59 (m, 4H), 8.37(m, 3H),
11.39(s, 1H).
As shown in the scheme 1, 2-aryl-1-arylmethyl-
1H-benzimidazoles were synthesized in high yields
at room temperature. The results are summarized in
table 1. We have examined the catalytic efficiency of
Cu(NO3)2.3H2O towards anthranilamide and benzalde-
hyde reaction mixture at ambient temperature, 80◦C
afforded selectively 2-substituted quinazolinones with
excellent yield (93%). The reaction procedure was
extended to other aryl, heteroaryl and aliphatic aldehy-
des to observe the versatility of the catalyst also resulted
2j. IR spectrum,ν, cm−1: 1680, 1450, 1295, 1200,
1137, 954, 771. 1H NMR spectrum (300 MHz, DMSO),
δ, ppm (J, Hz):1.34(t, 3H, J = 9.4 Hz), 2.62(q, 2H, J =
5.8 Hz), 7.42 (m, 4H), 11.40 (s, 1H).
2k. IR spectrum,ν, cm−1: 1680, 1450, 1295,1208,
1
958,771. H NMR spectrum (300 MHz, DMSO), δ,
ppm (J, Hz): 1.09 (t, 3H, J = 8.7 Hz), 1.83(m, 2H),
2.62(t, 2H, J = 6.2 Hz), 7.42 (m, 4H), 12.04 (s, 1H).
Scheme 1. Synthesis of benzimidazoles.
Scheme 2. Synthesis of 4(3H)-quinazolinones.

4(3H)-quinazolinones and benzimidazoles
181
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