1019

Solvent-free syntheses of some quinazolin-4(3H)ones derivatives

S. Mohana Roopan, T. Maiyalagan, and F. Nawaz Khan

Abstract: Solvent-free syntheses of quinazolin-4(3H)-ones were performed by reaction of anthranillic acid with different amides, such as nicotinamide, benzamide, formamide, etc., on montmorillonite K-10. Products were confirmed by
FTIR, 1HNMR, and 13CNMR spectroscopic techniques. All synthesized compounds exhibited antioxidant properties and
have been compared with standard antioxidant BHT.
Key words: quinazolinone, montmorillonite K-10, solvent-free conditions, antioxidant properties.
Rsum : On a ralis des synthses sans solvant de quinazolin-4(3H)-ones par raction de lacide anthranillique avec
divers amides, tel le nicotinamide, le benzamide et le formamide sur de la montmorillonite K-10. Les produits ont t
caractriss par la spectroscopie infrarouge avec transforme de Fourier (IR-TF), et par les mthodes spectroscopiques
de RMN du 1H et du 13C. Tous les produits synthtiss prsentent une proprit antioxydante et ils ont t compars
avec lantioxydant standard, BHT.
Mots-cls : quinazolinone, montmorrillonite K-10, conditions sans solvant, proprits antioxydante
[Traduit par la Rdaction]

Roopan et al.

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Introduction
The quinazoline ring skeleton is widely found in alkaloids
and many biologically active compounds. In general, quinazolones were considered important compounds in the fields
of pharmacology and biology (1) because of their wide range
of strong biological activities (26). Some of these compounds are identified as drugs (7) and as diuretics. Among
this class of molecules, quinazolin-4-ones and their derivatives are well-known to possess an array of physiological
activities, e.g., antitubercular (8), antifungal (9), antibacterial
(10), anti-inflammatory, anticancer (11), and anti-proliferative
(5) activities.
Quinazolin-4(3H)-one was prepared by many methods (5,
8, 1013). However, quinazoline derivatives were synthesized mainly by a common approach involving amidation,
starting from anthranilic acid, 2-aminobenzonitrile, and 2aminobenzamide. Other methods included the condensation
of anthranilic acid, ammonium acetate, and the orthoesters
(14), reaction of imidates and anthranilic acid (15), reaction
of polymer-bound isothioureas with isatoic anhydride derivatives (16), and were associated with drawbacks such as
multistep procedures (17), costly reagents, harse reaction
conditions, complex experimental procedures, and low
yields (18). Previous methods have been excluded from
practical applications because of environmental and economic considerations. Finding an efficient method for the
synthesis of quinazolin-4(3H)-one is still a challenge. Nowadays, solvent-free organic reactions have led to experimen-

tally and industrially important organic syntheses that are

more effective and eco-friendly than conventional reactions
(19, 20).
In continuation of our interest in CC bond-forming reactions (2125), we have explored a one-pot synthesis of
quinazolin-4(3H)-ones (Schemes 1 and 2, Tables 1 and 2)
from anthranillic acid and amides, such as formamide,
acetamide, benzamide, nicotinamide, etc., in the presence of
montmorillonite K-10 catalyst and other inorganic catalysts
such as acidic alumina, bentonite, etc., (Table 3), under
solvent-free conditions. The above reactions, carried out
over montmorillonite K-10 clay, give good yields because of
the ditopic nature (26, 27) of montmorillonite K-10 clay.
However, the reaction takes less time to complete. The optimization of catalyst amount was also done (Table 4). Thus,
we have developed a simple, economical, and environmentally benign synthesis of classical procedures, by avoiding
volatile and toxic organic solvents. The reusability of the
catalyst in synthesis has also been explored (Table 5). Scope
of the reaction (Tables 1 and 2) and antioxidant properties of
the reaction products have also been discussed.

Experimental
Anthranillic acid and amides used for the reaction were
from Sigma-Aldrich Co., and montmorillonite K-10 was obtained from Fluka. The substances were used as provided
with no other purification. Melting points were taken in
open capillary tubes and are corrected with reference to ben-

Received 17 March 2008. Accepted 29 August 2008. Published on the NRC Research Press Web site at canjchem.nrc.ca on
8 October 2008.
S.M. Roopan, T. Maiyalagan,1 and F.N. Khan.1 School of Science and Humanities, Organic Chemistry Division, VIT University,
Vellore 632 014, Tamil Nadu, India.
1

Corresponding authors (e-mail: maiyalagan@gmail.com, nawaz_f@yahoo.co.in).

Can. J. Chem. 86: 10191025 (2008)

doi:10.1139/V08-149

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Can. J. Chem. Vol. 86, 2008

Table 1. Synthesis of 2-substituted quinazolinone by solvent-free montmorillonite K-10 catalysis.

Scheme 1. Montmorillonite K-10 catalysed reaction of

anthranillic acid and different amides.

Scheme 2. Montmorillonite K-10 catalysed reaction of

anthranillic acid with urea and thiourea.

zoic acid. IR spectra in KBr pellets were recorded on Nucon

infrared spectrophotometer. Nuclear Magnetic Resonance
(1H and 13C) spectra were recorded on a Bruker Spectrospin
Avance DPX400 Ultrashield (400 MHz) spectrometer.
Chemical shifts are reported in parts per million ()
downfield from an internal tetramethylsilane reference.

General procedure for the synthesis of 2-substituted3H-quinazolin-4-ones and 1H,3H-quinazolin-2,4-diones

A mixture of anthranillic acid, 1 amide, 2 or 4a or 4b, and
montmorillonite K-10 clay when heated under reflux
conditions gave 2-substituted-3H-quinazolin-4-one 3 or
1H,3H-quinazolin-2,4-dione 5 (Scheme 1). After completion
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Table 1 (concluded).

Note: 1 = 10 mmol, 2 = 10 mmol, catalyst = 0.1 g.

a
3 in isolated yields after column chromatography.
b
All products were characterized by 1H NMR and IR spectroscopic data and their melting points were compared with
literature values (3132).

of the reaction, ethyl acetate was added to the reaction mixture, and the catalyst was recovered by filtration. Filtrate
was washed with a 10% NaHCO3 solution to remove any
unreacted acid and further washed with water to remove any
inorganic materials. The organic layer was dried, solvent
evaporated to obtain the products. FT-IR and NMR spectral
techniques were used for product analysis.

Synthesis of 2-pyridin-3-yl-3H-quinazolin-4-one (3a)

Anthranillic acid 1 (10 mmol), nicotinamide 2a
(10 mmol), and montmorillonite K-10 (0.1 g) were placed in
a mortar and mixed well, transferred to a 50 mL roundbottomed flask, and refluxed at 150 C for 30 min. The reaction was monitored by TLC, and after completion of the reaction, work-up was performed as above to give crude
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Can. J. Chem. Vol. 86, 2008

Table 2. Synthesis of quinazolidione by solvent-free montmorillonite K-10 catalysis.

Note: 1 = 10 mmol, 4 = 10 mmol, catalyst = 0.1g.

a
5 in isolated yields.

Table 3. Selection of catalyst.

Refluxing at 150 C solvent-free conditions
Sl. No.

Catalyst used

Catalyst amount (mg)

Time (h)

Product 3a

1
2
3
4
5

Silica gel
Bentonite
Montmorillonite KSF
Acidic alumina
Montmorillonite K10

10
10
10
10
10

4
4
4
4
0.5

Nil
Nil
Nil
Low yield
High yield

Note: Anthranilic acid 1 (1 mmol) and nicotinamide 2a (1 mmol).

Table 4. Optimization of catalyst concentration.

Refluxing at 150 C solvent-free conditions
Sl. No.

Amide, R
RCONH2

Montmorillonite
K-10 (g)

Time
(h)

Product 3a
(R)

Yielda
(%)

1
2
3
4
5
6
7
8

-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N

None
0.02
0.04
0.06
0.08
0.1
0.12
0.14

2
1
1
1
0.5
0.5
0.5
0.5

-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N
-C5H4N

40
59
67
65
71
85
86
86

Note: 1 = 10 mmol, 2a = 10mmol, refluxed at 150 C.

a
3a in isolated yields.

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Table 5. Life cycle of catalyst.

Entry

Cycle No.

Catalyst
amount (g)

Yield
(%)

1
2
3

Cycle I
Cycle II
Cycle III

0.1
0.096
0.091

85
82
81

Fig. 1. Time vs. absorbance graph for antioxidant property of

quinazolinone derivatives.

product. Pure 2-pyridin-3-yl-3H-quinazolin-4-one 3a was

obtained by performing column chromatography using silica
gel and petroleum ether/ethyl acetate as eluent. Yield was
determined (Table 1, compound 3a). The quinazolinone 3a
was recrystallized from petroleum ether and ethyl acetate.
The melting point was found to be 114 C.
A similar procedure was followed to obtain other
quinazolinone derivatives 3 from different amides 2
(Scheme 1 and Table 1). Products were characterized by
FTIR, 1HNMR, 13CNMR, and GCMS spectral techniques,
and known compounds were compared with literature reports. The recrystallization of products was effected using
petroleum ether and ethyl acetate.
Synthesis of 1H,3H-quinazolin-2,4-dione (5a)
A mixture of anthranillic acid 1 (10 mmol), urea 4a
(10 mmol), and 0.1 g of montmorillonite K-10 was heated
under reflux conditions (150 C) for 2 h. After completion
of the reaction, the catalyst was removed by filtration; the
mixture was poured into ice-cooled water and extracted with
ethyl acetate. The product 5a, obtained after solvent removal, was purified by performing column chromatography
using silica gel and petroleum ether/ethyl acetate as eluent
(Scheme 2, Table 2). The quinazolindione 5a was
recrystallized from petroleum ether and ethyl acetate. The
melting point was found to be >300 C.
Synthesis of 2-thioxo-2,3-dihydro-1H-quinazolin-4-one
(5b)
A mixture of anthranillic acid 1 (10 mmol), thiourea 4b
(10 mmol), and 0.1 g of montmorillonite K-10 was heated
under reflux conditions (150 C) for 2 h. After completion
of the reaction, the catalyst was removed; the mixture was
poured into ice-cooled water and extracted with ethyl acetate. The product 5b, obtained after solvent removal, was purified by column chromatography (Scheme 2, Table 2). The
dihydroquinazolinone 5b was recrystallized from ethyl acetate. The melting point was found to be >300 C.
Life cycle of the catalyst
The reusability of catalyst was explored by checking the
successive runs of the reactions on recycled catalyst; i.e., after first run of the reaction, the catalyst was recovered by a
simple filtration from reaction mixture, washed with ethyl
acetate, and dried. Then it was utilized in the second run of
the reaction. It was noticed that use of recycled catalyst in
subsequent experiments gave similar yields (Table 5). Thus,
the catalyst is not leached.
Free-radical scavenging activity of quinazolinone
derivatives
Radical scavenging activities are very important due to the
deleterious role of free radicals in foods and biological sys-

tems. In this study, the free-radical scavenging activity of

quinazolin-4(3H)-ones derivative was measured by a 1,1diphenyl-2-picryl-hydrazyl (DPPH) method. This activity
was measured by the following Blos methodology as assessed by Ansari et al. (28). The absorbance of DPPH is
monitored at a characteristic wavelength in the presence of a
synthesized sample. In its radical form, DPPH absorbs at
517 nm, but upon reduction by an antioxidant or a radical
species its absorption decreases. Briefly, a 1.5 104
mmol/L solution of DPPH in ethanol was prepared and 1
mL of this solution was added to 3 mL of 1.5 104 mmol/L
of quinazolinone in ethanol. At each 5 min interval,
absorbance was measured at 517 nm until 30 min. The standard used was butylated hydroxyl toluene (BHT), (1.5 10
4
mmol/L) in ethanol solution. Lower absorbance of reaction
mixture indicates higher free-radical scavenging activity.
Absorbance of the DPPH (control) is 1.544. The capability
to scavenge DPPH radical (28, 29) was calculated using the
following equation,
DPPH Scavenging effect (%)
= [(Acontrol Asample / Acontrol) * 100]
where Acontrol is the absorbance of the DPPH solution and
Asample is the absorbance in the presence of quinazolinone.
Two different graphs (Figs. 1 and 2) are plotted with time
vs. absorbance and time vs. % inhibition.

Results and discussion

Solvent-free syntheses of quinazolinone 3a from
anthranillic acid 1 and nicotinamide 2a have been explored
by using inorganic catalysts such as montmorillonite K-10,
silica gel, acidic alumina, etc. (Table 3). Preliminary results
indicated the formation of quinazolinone in high yield only
in the case of montmorillonite K-10. The optimization of
catalyst amount was done to improve the yield (Table 4).
Montmorillonite K-10 has had a great impact in organic synthesis and has offered major breakthroughs for the manufacture of fine chemicals. This reagent has advantages over the
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Fig. 2. Time vs. % inhibition graph for antioxidant property of
quinazolinone derivatives.

Can. J. Chem. Vol. 86, 2008

compared with commercial antioxidant butylated hydroxyl

toluene (BHT). 2-Thioxo-2,3-dihydro-1H-quinazolin-4-one
had relatively high DPPH radical-scavenging activity. As
shown in Figs. 1 and 2, all quinazolinone derivatives were
found to have the ability to scavenge hydroxyl radical at a
concentration of 1.5 104 mmol/L.
Analytical data
Data of the new compound 3a and that of a few known
compounds, 3b3d, 5a5b, which have not been reported
earlier are given below. The data of a few compounds that
have been found to be identical to those reported (3032) are
given as Supplementary Data available with this paper.2

conventional homogeneous solution techniques: easy set-up

and work-up, mild experimental conditions, and high yield.
As part of our research, quinazolin-4(3H)-ones were synthesized using K-10 as catalyst (Schemes 1 and 2). The results
of the quinazolinones synthesis are summarized (Tables 1
5). The essence of the catalyst can be understood from the
following facts: when anthranillic acid 1 was treated with
montmorillonite K-10 under conventional heating in the
presence of nicotinamide 2a, the product 3a was obtained in
quantitative yield (Table 3, entry 5). When the same reaction
was performed without montmorillonite catalyst, 3a was
obtained in much lower yield in 2 h (Table 4, entry 1). The
reaction optimization with different amounts of montmorillonite K-10 was carried out, and at 0.1 g, the yield was good
(Table 4).
In the IR spectra of all 4-quinazolinones 3, absorption
bands are observed in the region of 16901730 (Ar C=O),
16001635, 15101570, 14601500 cm 1 (the quinazolone
ring). Assignments of 1H NMR signals of quinazolinones 3
were derived from splitting patterns and characteristic chemical shift values. The data consistently show that the
homocyclic proton signal with the lowest field shift in series
of compounds is a doublet with additional fine structure due
to further meta and para couplings. This signal is assigned
to H-5 on the basis of the proximity to the carbonyl group.
The assignment of H-5 led to the assignment of H-8 by default. In the same spectral region, the signal for H-2 is found
as a singlet. The signals for protons H-6 and H-7 show two
ortho couplings. We have assigned the H-7 signal to the
lower field.
In the present study, quinazolinone derivatives were evaluated for their free-radical scavenging activity using the
DPPH radical assay. Reduction of DPPH radicals can be observed by a decrease in absorbance at 517 nm. Different derivatives of quinazolinones reduced DPPH radicals
significantly. The activity of quinazolinone derivatives was
2

2-Pyridin-3-yl-3H-quinazolin-4-one (3a)
Colourless solid, mp 114 C. IR (KBr pellets, cm1) :
3351.67, 1655.03, 1601.16, 1585.32, 1535.27, 1491.45. 1H
NMR (300MHz, CDCl3) : 9.1 (s, 1H), 8.768.75 (d, J =
4.56Hz, 1H), 8.238.20 (d, J = 7.77Hz, 1H), 8.13 (s, 1H),
7.667.64 (d, 1H), 7.467.41 (m, 1H), 7.397.36 (d, J =
7.56, 2H), 7.217.16 (m, 1H). 13C NMR (100 MHz, CDCl3)
: 163.92 (C=O), 152.37, 147.82, 137.49, 135.49, 130.86,
129.17, 125.08, 123.73, 120.51. EI-Mass: 223. GC-MS m/z
223 (M+) C13H9N3O (mol. wt. 223.23) calcd.: C 69.95, H
4.06, N 18.82, O 7.17; found: C 69.83, H 4.14, N 18.75, O
7.01.
2-Phenyl-3H-quinazolin-4-one (3b)
Mp 242246 C (lit. value (32), 242246 C). IR (KBr
pellets, cm1) : 3342.55, 1654.76, 1437.47. 13C NMR
(100MHz, CDCl3) : 165.70 (C=O), 137.85, 134.93, 131.78,
129.03, 128.72, 126.95, 124.51, 120.14. C14H10N2O (mol.
wt. 222.24) calcd.: C 75.66, H 4.54, N 12.60, O 7.20; found:
C 75.54, H 4.46, N 12.52, O 7.11.
2-Methyl-3H-quinazolin-4-one (3c)
Mp 240248 C (lit. value (32), 238240 C). IR (KBr
pellets, cm1) : 3295.81, 1666.07, 1434.67. C9H8N2O (mol.
wt. 160.17) calcd.: C 67.49, H 5.03, N 17.49, O 9.99; found:
C 67.31, H 5.13, N 17.51.
3H-Quinazolin-4-one (3d)
White solid, mp 216 C (lit. value (32), 215216 C). IR
(KBr pellets, cm1) : 3428.88, 1704.98, 1665.87. 13C NMR
(75MHz, CDCl3) : 143.34, 134.89, 127.76, 127.42, 126.35.
C8H6N2O (mol. wt. 146.15) calcd.: C 65.75, H 4.14, N
19.17, O 10.95; found: C 65.80, H 4.03, N 19.04, O 10.86.
(4-Oxo-quinazolin-2yl)-acetonitrile (3e)
Colourless solid, mp 240 C (lit. value (32), 242 C.
C10H7N3O (mol. wt. 185.18) calcd.: C 64.86, H 3.81, N
22.69, O 8.64; found: C 64.74, H 3.91, N 22.57, O, 8.58.
2-(4-Methylphenyl)quinazolin-4(3H)-one (3g)
Colourless solid, mp 240 C (lit. value (31), 239 C). 13C
NMR (75MHz, CDCl3) : 159.9, 147.34, 146.20, 134.31,
133.20, 131.58, 128.15, 127.12, 126.35, 125.14, 124.81,
124.13, 122.11, 19.30. GC-MS m/z 236 (M+).

Supplementary data for this article are available on the journal Web site (canjchem.nrc.ca) or may be purchased from the Depository of
Unpublished Data, Document Delivery, CISTI, National Research Council Canada, Ottawa, ON K1A 0R6, Canada. DUD 3833. For more
information on obtaining material refer to cisti-icist.nrc-cnrc.gc.ca/cms/unpub_e.shtml.
2008 NRC Canada

Roopan et al.

2-(4-Methoxyphenyl)quinazolin-4(3H)-one (3h)
Pale yellow, mp 245247 C (lit. value (31), 244 C). 13C
NMR (75MHz, CDCl3) : 161.22, 148.33, 146.20, 134.32,
133.20, 131.56, 128.11, 127.10, 126.22, 125.14, 124.81,
124.21, 122.13, 19.31. GC-MS m/z 252 (M+).
2-(4-Chlorophenyl)quinazolin-4(3H)-one (3j)
Colourless solid, mp 306308 C (lit. value (31), 312 C).
13
C NMR (75MHz, CDCl3) : 160.12, 147.73, 146.64,
136.45, 135.26, 134.66, 132.62, 130.55, 128.33, 127.91,
126.84, 124.14, 122.43, 19.31. GC-MS m/z 240 (M+).
1H,3H-Quinazolin-2,4-dione (5a)
Pale yellow solid, mp >300 C (lit. value (32) >280 C).
IR (KBr pellets, cm1) : 3367.88 (br), 1673.92, 1609.99.
C8H6N2O2 (mol. wt. 162.15) calcd.: C 59.26, H 3.73, N
17.28, O 19.73; found: C 59.14, H 3.67, N 17.16, O 19.82.
2-Thioxo-2,3-dihydro-1H-quinazolin-4-one (5b)
Colourless solid, mp >300 C. IR (KBr pellets, cm1) :
3406.32, 3203.67, 3008.42, 1696.52, 1263.87. 1H NMR
(400MHz, CDCl3) : 7.89 (s, 1H, NH), 7.457.44 (d, 1H),
7.437.42 (d, 1H), 7.417.37(m, 2H) 7.34 (s, 1H, NH). 13C
NMR (100MHz, CDCl3) : 179.94 (C=S), 137.05, 129.62,
127.15, 125.30. C8H6N2OS (mol. wt. 178.21) calcd.: C
53.92, H 3.39, N 15.72, O 8.98, S 17.99; found: C 53.84, H
3.48, N 15.81, O 8.87, S 17.87.

Conclusion
In conclusion, we have reported a facile synthesis of
quinazolin-4(3H)-ones under solvent-free conditions and
conventional heating, demonstrating the use of montmorillonite K-10 as an efficient, rapid, mild, and inexpensive catalyst. The procedure has the advantages of simplicity and
easy product isolation, coupled with high purity and yields.

Acknowledgement
The authors wish to express their gratitude to Syngene
International Limited for their support of their NMR and
GCMS facilities to carry this research work.

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