Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia

Article abstract of DOI:10.1007/s12039-015-0890-2

A simple, green and cost-effective protocol was achieved for the synthesis of tri/tetrasubstituted-1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride. The reaction was carried out under catalyst-free conditions and the products were isolated in good to excellent yield. [Figure not available: see fulltext.]

Full text of DOI:10.1007/s12039-015-0890-2

c
J. Chem. Sci. Vol. 127, No. 7, July 2015, pp. 1221–1228. ꢀ Indian Academy of Sciences.
DOI 10.1007/s12039-015-0890-2
Green synthesis of tri/tetrasubstituted 1H-imidazoles and
2,3-dihydroquinazolin-4(1H)-ones using nano aluminium
nitride as solid source of ammonia
MARYAM HAJJAMI∗, ARASH GHORBANI-CHOGHAMARANI, ZAKIEH YOUSOFVAND and
MASOOMEH NOROUZI
Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran
e-mail: mhajjami@yahoo.com; m.hajjami@ilam.ac.ir
MS received 17 December 2014; revised 19 March 2015; accepted 28 March 2015
Abstract. A simple, green and cost-effective protocol was achieved for the synthesis of tri/tetrasubstituted-
1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride. The reaction was carried
out under catalyst-free conditions and the products were isolated in good to excellent yield.
Keywords. Imidazoles; 2,3-dihydroquinazolin-4(1H)-ones; nano aluminium nitride; multicomponent;
one-pot.
1. Introduction
Many of the synthetic methods for imidazoles suffer
from one or more disadvantages such as low yields,
harsh reaction conditions, prolonged time period and
application of hazardous and often expensive acid cat-
alysts and expensive catalysts long reaction times.17
Moreover, the synthesis of these compounds is usually
carried out in polar solvents such as ethanol, methanol,
acetic acid, dimethylformamide (DMF), and dimethyl-
sulfoxide (DMSO), leading to complex isolation and
recovery procedures.14
2,3-Dihydroquinazolin-4(1H)-ones, an important class
of heterocyclic compounds, influence numerous cellu-
lar processes.18 These exhibit a wide range of biological
activities, such as antitumor, antibiotic, antidefibrillatory,
antipyretic, analgesic, antihypertonic, diuretic, antihis-
tamine, antidepressant, and vasodilating behavior.19 Fur-
thermore, quinazolinone skeleton is frequently found in
various natural products. Some examples include the
anticancer compound trimetrexate, the sedative metha-
qualone, the alpha adrenergic receptor antagonist such as
doxazosin and the antihypertensive agent ketanserin.20
Environmental problems are expected to become
more serious in the 21st century. Therefore, the devel-
opment of simple, efficient, clean, high-yielding, and
environmentally friendly approaches without the use of
a catalyst or an organic solvent for the synthesis of these
compounds is an important task for organic chemists.
In recent years, polymer composite materials with
excellent thermal conductivity have attracted increasing
attention. Among them, nano-sized aluminium nitride
(nano-AlN) is a nontoxic, low cost substance, readily
available as high purity powder.21
Nitrogen-heterocyclic compounds (NHCs) are produced
for a variety of applications, including pharmaceuticals,
cosmetics, pesticides, disinfectants, agrochemicals, dy-
estuffs and antifreeze.1 In particular, derivatives of imi-
dazoles and hydroquinazolins are used as reagents in
industry.2 The five-membered imidazole ring is one of
the important substructures found in a large number of
natural products and pharmacologically active hetero-
cyclic compounds.3 The members of this class of com-
pounds are known to possess NO synthase inhibition
and antifungal, antimycotic, antibiotic, antiulcerative,
antibacterial, antitumor, and CB1 receptor antagonistic
activities.4 Among the imidazoles, 2,4,5-triphenylimi-
dazoles can be used as light-sensitive materials in pho-
tography, as inhibitors of IL-1 or p38 MAP kinase,
fungicides and herbicides and plant growth regulators.5,6
There are numerous methods in the literature for the
synthesis of highly substituted imidazoles: condensa-
tion of 1,2–diones, aldehydes, primary amines and am-
monia in the presence of several catalysts such as FeCl3·
6H2O,7 ionic liquids,8 K5CoW12O40.3H2O,9 HClO4-
10
SiO2 NaH2PO4,11 heteropolyacids,12 InCl3-3H2O,13
Bronsted acidic ionic liquid,14 MCM-41 or p-TsOH.15
In addition, they can also be accessed by hetero-Cope
rearrangement, condensation of a 1,2-diketone with an
aryl nitrile and primary amine under microwave irra-
diation, and N-alkylation of trisubstituted imidazoles.16
∗For correspondence
1221

1222
Maryam Hajjami et al.
n-hexan-acetate (4:1, v/v). After completion of the reac-
2. Experimental
tion, the product was dissolved in hot ethanol, fil-
tered and from the filtrate ethanol was removed by
evaporation. Finally, crude product 2-(4-chlorophenyl)-
2,3-dihydroquinazolin-4(1H)-one 3a were obtained by
recrystallization in the EtOH and water, yield (66%).
Chemicals were purchased from Sigma-Aldrich, Fisher,
and Merck. The tri/tetrasubstituted imidazole and 2,3
dihydroquinazolin-4(1H)-one derivatives were charac-
1
terized by H and 13C NMR spectra (1H NMR, 400
MHz; 13C NMR, 100 MHz) and IR. Scanning electron
microscopy (SEM) studies were conducted on a JSM
740 scanning electron microscope.
2.4 Characterization data of selected compounds
2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole 1a: M.p.:
254–256◦C. FT-IR-ATR (νmax, cm −1):3413, 3063,
2838, 1635, 1481, 1323, 1152, 830, 695. 1H NMR (400
MHz CDCl3): δ 7.87 (d J = 8.4 Hz 2H) 7.54 (d J =
6.8 Hz 4H) 7.45-7.30 (m 8H) ppm. 13C NMR (100
MHz CDCl3): δ 144.8 134.9 129.1 128.7 127.9 127.7
126.7 ppm.
2.1 Procedure for preparation of 2-(4-chlorophenyl)
-4,5-diphenyl-1H-imidazole 1a
To the mixture of 0.102 g (5 mmol) of aluminum
nitride, 0.140 g (1 mmol) of 4-chlorobenzaldehyde in a
few drops of water (0.3 mL), 0.210 g (1 mmole) ben-
zil was added at room temperature. The reaction ves-
sel was sealed and allowed to warm to 130◦C for 8 h
with constant stirring (the progress of the reaction was
monitored by TLC). After completion of the reaction,
the reaction mixture was cooled down to room temper-
ature and the crude product extracted by acetone. Ace-
tone was removed by simple evaporation. Finally, crude
product 2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole
1a was obtained by recrystallization from hot EtOH;
yield, 0.273 g (83%).
2-(4-bromophenyl)-4,5-diphenyl-1H-imidazole 1b: M.p.:
240–244◦C. FT-IR-ATR (νmax, cm −1):3323, 3061,
2835, 1645, 1481, 1322, 827, 694.1H NMR (400 MHz,
DMSO): δ 7.32-7.42 (m, 6H),7.53–7.55 (m, 4H),7.70
(d, 2H, J= 8.4 Hz), 8.05 (d, 2H, J= 8.4 Hz), 12.85 (br,
1H) ppm.
2-(3-Nitrophenyl)-4,5-diphenyl-1H-imidazole 1c: M.p.:
312-314◦C. FT-IR-ATR (νmax, cm −1): 3383, 3320,
3069, 1695, 1524, 1348, 1070, 697.
2.2 Procedure for preparation of 1,2-bis(4-chlorophe-
nyl)-4,5-diphenyl-1H-imidazole 2a
2-(naphthalen-2-yl)-4,5-diphenyl-1H-imidazole 1d: M.p.:
1
267-268◦C. H NMR(400 MHz, DMSO): δ 7.26(t,
To the mixture of 0.102 g (5 mmol) of aluminum
nitride, 0.140 g (1 mmol) of 4-chlorobenzaldehyde in
a few drops of water (0.3 mL), 0.210 g (1 mmol) ben-
zil and 0.127 g (1 mmol) 4-chloroaniline were added
at room temperature. The reaction vessel was sealed
and allowed to warm to 130◦C for over 8 h with con-
stant stirring (the progress of the reaction was moni-
tored by TLC). After completion of the reaction, the
reaction mixture cooled down to room temperature and
the crude product extracted by acetone. Acetone was
removed by simple evaporation. Finally crude product
1,2-bis(4-chlorophenyl)-4,5-diphenyl-1H-imidazole 2b
were obtained by recrystallization in the hot EtOH,
yield 0.316 g (72%) and M.p. 185–186◦C.
J = 14, 1H), 7.35 (m, 2H), 7.41(t, J = 14 Hz, 1H),
7.46–7.49 (m, 2H), 7.55–7.62 (m, 7H), 7.95–8.04 (m,
3H), 8.27(d, J = 8.4 Hz, 1H), 8.63 (s, 1H) ppm.13C
NMR(100 MHz, DMSO): δ 123.9, 124.2, 126.8, 127.1,
127.2, 127.6, 128.2, 128.3, 128.6, 128.7, 128.8, 128.9,
129.2, 130, 131.4, 133.2, 133.5, 135.6, 137.9, 138.5,
145.9 ppm.
4,5-diphenyl-2-(p-tolyl)-1H-imidazole 1e: M.p.: 227–
230◦C. FT-IR-ATR (νmax, cm−1): 3418, 3034, 29,87,
2793, 1600, 1586, 1321, 764,1H NMR (400 MHz,
CDCl3): δ 2.43(s, 3H), 7.24-7.40 (m, 8H),7.58 (br, 4H),
7.83 (d, 2H, J = 8 Hz), 9.30 (br, 1H) ppm.
2,4,5-Triphenyl-1H-imidazole 1f: Mp: 259–261◦C.
FT-IR-ATR (νmax, cm−1): 3404, 3038, 2962, 2852,
1601, 1408, 1071, 696.
2.3 Procedure for preparation of 2-(4-chlorophenyl)
-2,3-dihydroquinazolin-4(1H)-one 3a
A mixture of isatoic anhydride (0.234 g, 1 mmol),
aluminum nitride (1.5 mmol), 4-chlorobenzaldehyde 2-(3,4-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole 1g:
(1 mmol) was heated at 80◦C for 6 h. The reaction M.p.: 183–185◦C. FT-IR-ATR (νmax, cm−1): 3055,
was monitored by TLC analysis using petroleum and 2937, 1602, 1484, 1263, 1024, 698.

Green Synthesis using nano aluminium nitride
1223
2-(anthracene-9-yl)-4,5-diphenyl-1H-imidazole 1h: M.p.: 3-(1-benzyl-4,5-diphenyl-1H-imidazol-2-yl)phenol 2d:
219–220◦C. FT-IR-ATR (νmax, cm−1): 3381, 3048, M.p.: 229–231◦C. FTIR (KBr, cm−1): 3059, 3031,
1
3069, 1598, 1443, 1342, 1079, 695. H NMR (400 1598, 1457, 1234, 695.
MHz CDCl3): δ 7.34–7.50 (m 10H), 7.96 (d, J = 7.2
Hz, 2H), 8.50 (s, 1H), 9.87 (b, 1H) ppm. 13C NMR
(100 MHz, CDCl3): δ143.6, 131.5, 131.1, 129, 128.6,
128.5, 127.9, 127.5, 126.6, 125.8, 125.4, 125 ppm.
Hz, 4H), 7.93 (d, J = 8.8 Hz, 2H), 8.02 (d, J = 8.4
1-benzyl-2-(3,4-dimethoxyphenyl)-4,5-diphenyl-1H-imi-
dazole 2e: M.p.: 161–163◦C. FTIR (KBr, cm−1):
3322, 3052, 3001, 1602, 1529, 1484, 1263, 698.
1-benzyl-2-(2-nitrophenyl)-4,5-diphenyl-1H-imidazole
5-bromo-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol 1i: M.p:
2f: M.p.: 144–148◦C. FTIR (KBr, cm−1): 3059, 3031,
◦
221-224 C. FTIR (KBr, cm−1): 3417, 3392, 3210,
2925, 1602, 1497, 1300, 1076, 692.
2680, 1644, 1487, 712.
2-(4-bromophenyl)-1,4,5-triphenyl-1H-imidazole 2g:
M.p.: 179–183◦C. FTIR (KBr, cm−1): 3055, 1597,
1477, 1446, 1071, 831, 694.
2-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazole 1j: M.p.:
221–224◦C. FTIR (KBr, cm−1): 3034, 2987, 1600,
1321, 1261, 764. 1H NMR (400 MHz, DMSO): δ 3.82
(s, 3H), 7.06 (d, J= 8.8 Hz, 2H), 7.37 (m, 6H), 7.52 (d,
J=6.4 Hz, 4H), 8.03 (d, J= 8.8 Hz, 2H), 12.5 (br,1H)
ppm. 13C NMR (100 MHz, DMSO): δ 55.6, 114.6,
123.2, 127.3, 127.7, 128.2, 128.9, 146.2, 159.9 ppm.
1,4,5-triphenyl-2-(p-tolyl)-1H-imidazole 2h: M.p.: 175–
178◦C. FTIR (KBr, cm−1): 3042, 2919, 1595, 1414,
1024, 695.
1-(4-chlorophenyl)-2-(4-chlorophenyl)-4,5-diphenyl-1H- 2-(4-chlorophenyl)-1,4,5-triphenyl-1H-imidazole 2i:
imidazole 2a: Isolated Yield = 72%. M.p.: 185– M.p.: 172–174◦C. FTIR (KBr, cm−1): 3060, 1597,
186◦C.1H-NMR (CDCl3, 400MHz); δ 6.99 (d, 2H, 1496, 1446, 1082, 837, 698.
J=8.4), 7.14–7.16 (m, 2H), 7.23–7.33(m, 10H), 7.39(d,
2H, J =8.8), 7.61 (d, 2H, J =8.4) ppm.
4-(1,4,5-Triphenyl-1H-imidazol-2-yl)-phenol 2j: M.p.:
279–280◦C. FTIR (KBr, cm−1): 3448, 3057, 2974,
2613, 1604, 1492, 1273, 696.
1-benzyl-2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole
2b: M.p.: 161–164◦C. FTIR (KBr, cm−1): 3059,
3030, 2938, 1662, 1446, 1085, 693.
2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one
1
3a: M.p.: 204–207◦C. H NMR (250 MHz, DMSO-
d6): δ 8.29 (s, 1H), 7.61–7.41 (m, 5H), 7.26–7.2 (t,
1H), 7.12 (s, 1H), 6.75–6.63 (m, 2H), 5.75 (s, 1H) ppm.
13C NMR (62 MHz, DMSO-d6): δ 163.9, 148.1, 141.1,
1-benzyl-2-(4-bromophenyl)-4,5-diphenyl-1H-imidazole
2c: M.p.: 162–165◦C. FTIR (KBr, cm−1): 3055, 1597,
1496, 1071, 694.
Scheme 1. Synthesis of 2,4,5-trisubstituted imidazoles.
Scheme 2. Synthesis of 1,2,4,5-tetrasubstituted imidazoles.

1224
Maryam Hajjami et al.
133.8, 133.4, 129.2, 128.7, 127.8, 117.7, 115.4, 114.9,
66.2 ppm.
Initially, the effect of reaction time on the yield was
investigated (table 1, entry 1-5). The reaction took place
quickly at first and gradually reached the balance after
8 h. The yield changed little after 8 h. Also, the effect
of reaction time on the condensation, a one-pot reaction
of isatoic anhydride, aldehyde and aluminum nitride for
the synthesis of substituted quinazolin-4(1H)-ones,32,33
3a–3e in water was investigated (scheme 3). When reac-
tion time was increased gradually from 3 to 6 h, the rate
ofthe reaction increased from 2 to 63%. Increase of time
to 7 h has less effect on the yield (66%) of the reaction.
We carried out the study in search for optimal amount
of aluminum nitride for the proposed transformation
using as a model the reaction involving 1 mmol of
4-chlorobenzaldehyde, 1 mmol of benzil for 2,4,5-
trisubstitution and also 1 mmol of 4-chloroaniline for
synthesis of 1,2,4,5-tetrasubstituted imidazole deriva-
tives in the presence of different amounts of nano alu-
minum nitride in few drops of water (0.3 mL) at 130◦C
was conducted, and the significant data obtained as a
function of the amount of aluminum nitride are shown
in (figure 1, 1a and 2b). The best results were obtained
with 5 mmol of aluminum nitride in the presence of
a few drops of water (0.3 mL) and under solvent-free
conditions after 8 h.
2-(4-methylphenyl)-2,3-dihydroquinazolin-4(1H)-one
1
3d: M.p.: 220–225◦C. H NMR (250 MHz, DMSO-
d6): δ 8.21 (s, 1H), 7.62–7.59 (d, 1H), 7.38–7.35 (d,
2H), 7.26–7.16 (m, 3H), 7.03 (s, 1H), 6.75–6.63 (m,
2H), 5.71 (s, 1H), 2.49–2.42 (s, 3H) ppm. 13C NMR
(62 MHz, DMSO-d6): δ 164.1, 148.4, 139.1, 138.2,
133.7, 129.3, 127.8, 127.2, 117.5, 115.4, 114.9, 66.8,
21.2 ppm.
3. Results and Discussion
In continuing our investigations on the synthetic organic
reactions,22–25 in efforts to develop an efficient pro-
cedure for the synthesis of substituted imidazole and
quinazolin-4(1H)-one derivatives, we report the syn-
thesis of tri/tetrasubstituted imidazole and quinazolin-
4(1H)-ones, via one-pot and multi-component conden-
sation using aluminium nitride under solvent-free or
water as solvent conditions.
It was found that benzil could be condensed
with aromatic aldehydes and nano aluminum nitride
to smoothly afford 2,4,5-trisubstituted-1H-imidazole
derivatives, 1a–1j with excellent yields at 80◦C under
solvent-free condition in the presence a few drops of
water (0.3 mL) (scheme 1). The same reaction with an
additional amine yielded 1,2,4,5-tetrasubstituted-1H-
imidazole derivatives 2a-2j (scheme 2).
Table 1. Optimization of reaction timea.
Entry
AlN (mmol)
Time (h)
Yield (%)
1
2
3
4
5
4
4
5
4
5
3
5
6
8
8
10
50
68
69
83
aMolar ratio of the reagents: 4-chlorobenzaldehyde 1 mmol,
benzyl 1 mmol.
Figure 1. Optimization of the amount of aluminum nitride
for the synthesis of substituted imidazole.
bIsolated yield.
Scheme 3. Synthesis of substituted quinazolin-4(1H)-ones.

Green Synthesis using nano aluminium nitride
1225
Under optimized conditions for aluminum nitride,
the scope of synthesis of 2,4,5-trisubstituted imidazole
derivatives with other aldehydes was found to be quite
good. As shown in (table 2), the method has the ability
to tolerate a variety of functional groups such as chloro,
nitro, methoxy and methyl.
Then, under these conditions, 1,2,4,5-tetrasubstituted
imidazole derivatives were formed cleanly, The results
(table 3) clearly indicate the feasibility of four-com-
ponent reaction. The products were synthesized in good
yield and a variety of different substituted aldehydes
and amines were subjected to this reaction.
100
90
80
70
60
50
40
30
20
10
0
Yield (3e)
1
1.5
2
Amount of AlN (mmol)
The optimized reaction conditions were extended to
the condensation of other aldehydes with isatoic anhy-
dride and aluminum nitride at 80◦C. Aromatic aldehy-
des bearing both electron-deficient and electron-rich
substituents afforded the desired 2,3-disubstituted dihy-
Figure 2. Optimization of the amount of aluminum nitride
for the synthesis of substituted quinazolin-4(1H)-ones.
In order to study we optimized the synthesis of droquinazolin-4(1H)-one in good yields (table 4).
substituted quinazolin-4(1H)-ones with various amount
Major advantage of this protocol is the simplicity
(mmol) of nano AlN. The condensation, a one-pot reac- of operation and isolation of the products, which have
tion of isatoic anhydride (1 mmol), 3-nitrobenzaldehy- been achieved by simple washing and crystallization of
de (1 mmol) was chosen as a model reaction (figure 1). the crude products.
Aluminum nitride plays a major role in the product
The scanning electron microscope (SEM) images of
yield. It was observed that increasing the loading of the nano aluminium nitride showed that the resulting par-
nano AlN from 1 to 1.5 mmol gave an improved yield of ticles were irregular sphere structure with the particle
63% of the product (figures 2, 3e). Further increase of size is about 40 nm (figure 3a). In the presence of
aluminum nitride loading leads to lower reaction yields. water, the nano AlN will be decomposed to form
Figure 3. SEM images: (a) nano AlN, (b) nano AlN in reaction and (c) Al(OH)3 after reaction.

1226
Maryam Hajjami et al.
Table 2. Synthesis of 2,4,5-trisubstituted imidazole derivativesa.
Entry
R
Product
Yieldb (%)
Mp (◦C) found (reported)
1
2
3
4
5
6
7
8
9
10
4-ClC6H4
4-BrC6H4
3-NO2C6H4
C10H7
4-CH3C6H4
C6H5
1a
1b
1c
1d
1e
1f
1g
1h
1i
83
70
79
80
74
72
80
98
86
84
254-256 (259–269)26
240-244(252–254)26
312-314(315–317)27
267-268(273-276)28
227-230(226–228)26
259-261(267–269)29
183-185(215)6
3,4-(OCH3)2C6H3
C14H9
5-Br-2-OHC6H3
4-OCH3C6H4
219-220
311-314(186–187)29
221-224(228–231)26
1j
aMolar ratio of the reagents: aluminum nitride/aldehyde/benzil (5 mmol/1 mmol
/1 mmol).
bIsolated yield.
Table 3. Synthesis of 1,2,4,5-tetrasubstituted imidazole derivativesa.
Entry
R1
R2
Product Yield (%)b Mp (◦C) found (reported)
1
2
3
4
5
6
7
8
9
10
4-ClC6H4
4-ClC6H4
4-BrC6H4
3-OHC6H4
4-ClC6H4
C6H5CH2
C6H5CH2
C6H5CH2
2a
2b
2c
2d
2e
2f
2g
2h
2i
72
77
83
93
93
81
70
71
76
81
185-186 (187-189)14
161-164(161–163)29
162-165(172-175)16
229-231(232–235)3
161-163
3,4-(OCH3)2C6H3 C6H5CH2
2- NO2C6H4
4-BrC6H4
4-CH3C6H4
2-ClC6H4
C6H5CH2
C6H5
C6H5
C6H5
C6H5
144-148(152–155)30
179-183(191–193)6
175-178(187–189)25
172-174(160–162)10
279-280(280–281)10
4-OHC6H4
2j
aMolar ratio of the reagents: aluminum nitride/aldehyde/amine/benzil (5 mmol/1
mmol/1 mmol/1 mmol).
bIsolated yield.
Table 4. Synthesis of 2,3- dihydroquinazolin-4(1H)-one derivativesa.
Entry
R
Product
Yieldb (%)
M.p. (◦C) found (reported)
1
2
3
4
5
4-ClC6H4
3-NO2C6H4
4-OCH3C6H4
4-CH3C6H4
C6H5
3a
3b
3c
3d
3e
66
73
66
62
63
204–207(205–2206)31
213–216 (216–217)31
189–193 (192–193)31
220–225(223–224)31
218–222(218–219)31
aMolar ratio of the reagents: aluminum nitride/aldehyde/isatoic anhydride (1.5 mmol/1
mmol/1 mmol).
bIsolated yield.
aluminum hydroxide and ammonia. These particles are
According to the results, the reaction can be mecha-
connected with each other without obvious boundaries. nistically considered as aluminum nitride generating a
SEM image showed that diameters of the particles in the solution of ammonia by reaction with water (scheme 4).
reaction mixture are approximately 1 μm (figure 3b). Based on this mechanism, the Al(OH)3 as a Lewis
After the reaction, the particle size increased and the acid participates in the reaction which activates the
average size of amorphous aluminum hydroxide is in aldehydes, benzil and isatoic anhydride followed by
the range of 500 nm (figure 3c).
nucleophilic addition of amines.

Green Synthesis using nano aluminium nitride
1227
Scheme 4. Possible mechanism.
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In conclusion, we have developed a new strategy that
provides an efficient way for the synthesis of tri/tetra-
substituted-1H imidazoles and 2,3-dihydroquinazolin-
4(1H)-ones using nano AlN as a source of ammonia.
Our method involves mild reaction conditions, very
simple and accessible starting materials. The key advan-
tages of this process are high yields, elimination of or-
ganic solvents and catalysts, easy work-up and puri-
fication of products by non-chromatographic methods.
Supplementary Information
Additional information pertaining to characterization
of the tri/tetrasubstituted imidazole and 2,3 dihydro-
quinazolin-4(1H)-one derivatives, namely, IR spectra,
1H and 13C NMR spectra are available at www.ias.ac.
in/chemsci.
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Acknowledgements
The authors acknowledge Ilam University, Ilam, Iran
for financial support of this work.
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