1,3-Dibromo 5,5-dimethylhydantoin (DBH) catalyzed, microwave-assisted rapid synthesis of 1-amidoalkyl-2-naphthols

Article abstract of DOI:10.1002/jccs.201100385

An expeditious synthesis of 1-amidoalkyl-2-naphthols by the condensation of 2-naphthole with various araldehydes and acetamide is described. This greener protocol is catalyzed by 1,3-dibromo 5,5-dimethylhydantoin (DBH), and proceeds efficiently in the abs

Full text of DOI:10.1002/jccs.201100385

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Article
1,3-Dibromo 5,5-Dimethylhydantoin (DBH) Catalyzed, Microwave-assisted Rapid
Synthesis of 1-Amidoalkyl-2-naphthols
Setareh Habibzadeha* and Hassan Ghasemnejad-bosrab
aIndustrial Noshirvani University, Babol, Iran
bDepartment of Chemistry, Babol Branch Islamic Azad University, Babol, Iran
(Received Jun. 21, 2011; Accepted Sept. 6, 2011; Published Online Sept. 15, 2011; DOI: 10.1002/jccs.201100385)
An expeditious synthesis of 1-amidoalkyl-2-naphthols by the condensation of 2-naphthole with various
araldehydes and acetamide is described. This greener protocol is catalyzed by 1,3-dibromo 5,5-di-
methylhydantoin (DBH), and proceeds efficiently in the absence of any organic solvent under thermal
condition and microwave irradiation in high.
Keywords: 1-Amidoalkyl-2-naphthols; 1,3-Dibromo 5,5-dimethylhydantoin (DBH); One-pot Syn-
thesis; Microwave.
INTRODUCTION
Multicomponent reactions (MCRs) are very impor-
RESULTS AND DISCUSSION
In continuation of on-going research on various
transformations by halogenating agents,26-33 herein is re-
ported the use of DBH as a more robust and efficient cata-
lyst in the one-pot synthesis of the 1-amidoalkyl-2-naph-
tols derivatives 4a-o by reaction of naphthalene-2-ol with
different aromatic aldehydes and acetamide under sol-
vent-free and microwave conditions in high yields.
(Scheme I).
tant and attractive subjects in organic synthesis due to for-
mation of carbon-carbon and carbon-hetero atom bonds in
one-pot.1-4 Simple procedures, high bond forming effi-
ciency, time and energy saving and low expenditures are
advantages of these reactions.5 Therefore, researchers have
made great efforts to find and develop new MCRs. Com-
pounds containing 1,3-amino-oxygenated functional groups
are frequently found in biologically active natural products
and potent drugs such as nucleoside antibiotics and HIV
protease inhibitors.6-9 Furthermore, 1-amidoalkyl 2-naph-
thols can be converted to useful and important biological
building blocks and to 1-amino methyl 2-naphthols by an
amide hydrolysis reaction, since compounds exhibit de-
pressor and bradycardia effects in humans.10,11 1-Amido-
alkyl 2-naphthols can be prepared by multicomponent
condensation of aldehydes, 2-naphthols and acetonitrile
or different amides in the presence of reagents such as
p-TSA,12 montmorillonite K10,13 Ce(SO4)2,14 Iodine,15
Fe(HSO4)3,16 Sr(OTf)2,17 K5CoW12O40.3H2O,18 sulfamic
acid,19,20 molybdophosphoric acid,21 cation-exchange res-
ins22 and silica sulfuric acid.23 However some of the re-
ported methods suffer from disadvantages such as pro-
longed reaction time, low yield of products, toxic and cor-
rosive reagents. Therefore, the discovery of clean proce-
dures and the use of green and eco-friendly catalysts with
high catalytic activity and short reaction times for the pro-
duction of 1-amidoalkyl 2-naphthols have gained consid-
erable attention.
Scheme I
Initially to optimize the amount of catalyst, the reac-
tion of 2-naphthol (1 mmol), benzaldehyde (1 mmol) and
acetamide (1.2 mmol) was performed under solvent-free
conditions at 100 oC in the presence of different quantities
of 1,3-dibromo 5,5-dimethyl hydantoin (DBH) (Table 1).
As shown in Table 1, the yields of product 4a using high
amounts of DBH were relatively low and the reaction time
was long (Table 1, entries 1–3). The yield of product 4a in
the presence of 0.11 mmol of DBH was higher than the oth-
ers (Table 1, entries 4). Therefore 0.11 mmol of catalyst
was chosen as the optimal quantity of DBH. It is also im-
portant to note that, no products were afforded when the re-
actions were carried out in the absence of DBH (Table 1,
* Corresponding author. Tel: +98-111-2267680; Fax: +98-111-2267555; E-mail: habibzadeh@nit.ac.ir
J. Chin. Chem. Soc. 2012, 59, 193-198
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
193

Article
Habibzadeh and Ghasemnejad-bosra
Scheme II.35 Thus, the 2-naphthole act as Michael accep-
tors and araldehydes as nucleophilic resulting in a Michael
adduct that under the influence of DBH initial forms of in-
termediate ortho-quinone methides (o-QMs) 5. The same
o-QMs, generated in-situ, have been reacted with acet-
amide to form 1-amidoalkyl-2-naphthol derivatives. A rea-
sonable explanation for this result can be given by consid-
ering the nucleophilic addition to o-QMs intermediate fa-
vorable via conjugate addition on a,b-unsaturated car-
bonyl group and under the influence of DBH that aro-
matizes ring of this intermediate.
Table 1. The effect of amount of DBH on the reaction of
naphtalen-2-ol, benzaldehyd and acetamide under
thermal solvent free conditions
Time (min)
Yield (%)a
Entry
Catalyst (mmol)
70
85
68
73
80
95
0
1
2
3
4
5
0.25
0.20
0.15
0.11
0.00
60
20
120
a Yields refer to the pure isolated products.
The advantages or the characteristic aspects of the
method described in this paper in comparison with other
previously reported ones are the following: the yields of
products were better than the previous reported yields and
in addition, the catalyst DBH is inexpensive, has no mois-
ture sensitivity, and no special measures are required for
the reaction.
entries 5).
Thus, we prepared arrange of 1-amidoalkyl-2-naph-
thols under the optimized reaction conditions: naphtha-
lene-2-ol (1 mmol), aldehyde (1 mmol) and acetamide (1.2
mmol) in the presence of DBH (0.11 mmol). A series of
amidoalkyl naphthols were prepared in high to excellent
yields by two methods (A, B) (Table 2).
In summary, the present methodology shows that
1,3-dibromo 5,5-dimethyl hydantoin (DBH) is an efficient
catalyst in the one-pot synthesis of 1-amidoalkyl-2-naph-
thols derivatives. The main advantages of the presented
protocol are mild, clean and environmentally benign reac-
tion conditions, as well as the high yields. Furthermore,
The electron withdrawing groups (EWD) substituted
on benzaldehyde in o-QM intermediate increase the rate of
1,4-nucleophilic addition reaction because of alkene LUMO
is at lower energy in the neighboring with-drawing groups
than electron donating groups (EDG).25 We proposed a
mechanism for these reactions five steps as shown in
Table 2. Synthesis of 1-amidoalkyl 2-naphthols in the presence of catalytic amount of DBH
under solvent-free microwave irradiation
M.p., oC
Method A
Method B
Entry Producta
R
Time/Yields (%)b Time/Yields (%)b
Found
Reportedc
1
4a
4b
4c
4d
4e
4f
H
4-Me
(20 min/95)
(25 min/93)
(24 min/92)
(26 min/94)
(25 min/89)
(28 min/89)
(27 min/90)
(18 min/94)
(19 min/93)
(18 min/95)
(19 min/94)
(17 min/92)
(17 min/93)
(18 min/96)
(21 min/94)
(4 min/95)
(5 min/94)
(7 min/93)
(5 min/90)
(6 min/95)
(8 min/89)
(7 min/93)
(9 min/92)
(7 min/89)
(6 min/90)
(4 min/94)
(6 min/92)
(7 min/93)
(6 min/92)
(6 min/95)
240-241
220-222
201-203
186-188
202-204
233-235
126-127
249-251
235-237
178-180
222-224
196-198
228-230
202-203
199-201
241-243
222-223
200-202
184-186
203-205
235-236
123-125
248-250
236-237
180-182
224-227
194-196
227-229
203-205
198-199
2
3
2-Me
4
4-OMe
3-OMe
3,4-OMe2
4-N(Me)2
4-NO2
3-NO2
2-NO2
4-Cl
5
6
7
4g
4h
4i
8
9
10
11
12
13
14
15
4j
4k
4l
2-Cl
4m
4n
4o
4-Br
4-F
2,4-Cl2
a Isolated yields. b All the products are known, characterized by IR, NMR spectral analysis
and compared with the authentic samples. c Melting points of compounds are consistent with
reported values.14,16,20,24,34
194
www.jccs.wiley-vch.de
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2012, 59, 193-198

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Synthesis of 1-Amidoalkyl-2-naphthols by MW under Solvent Free
Scheme II
tate/cyclohexane, 1:3), after the reaction was completed,
water (10 mL) was added and the product was filtered and
then recrystallized from ethyl alcohol.
Method B:
Aldehyde (1 mmol), naphthalene-2-ol (1 mmol),
acetamide (1.2 mmol) and DBH (0.11 mmol, 0.27 mg) were
taken in a 100 mL conical ask. The mixture was mixed well
and then irradiated in a microwave oven at 160 W for ap-
propriate time (see Table 1). After the reaction was com-
pleted, water (10 mL) was added and the product was fil-
tered and then recrystallized from ethyl alcohol.
All the products obtained were fully characterized by
spectroscopic methods such as IR, 1H NMR, 13C NMR and
mass spectroscopy and have been identified by the compar-
ison of the spectral data with those reported.16,24,34
N-[(2-Hydroxynaphthlen-1-yl)phenyl-methyl]acet-
amide 4a
o
White solid, m.p. 240-241 C, IR (KBr, vmax) 3392,
3254, 3068, 1981, 1687, 1572, 1540, 1452, 1355, 1270,
772 cm-1. 1H NMR (90 MHz, DMSO-d6): d 2.02 (s, 3H),
7.41-7.10 (m, 9H), 7.80-7.62 (m, 2H), 8.20-7.92 (d, J = 7.8
Hz, 2H), 9.67 (s, 1H). 13C NMR (22.5 MHz, DMSO-d6): d
23.74, 40.87, 118.25, 120.05, 120.18, 120.58, 122.07,
122.78, 123.20, 125.32, 126.91, 127.03, 131.52, 131.87,
132.08, 133.17, 148.12, 156.87, 169.65.
this method is also expected to find application in organic
synthesis due to the low cost of the reagent. It is believed
that this method will be a useful addition to modern syn-
thetic methodologies.
N-[(2-Hydroxynaphthlen-1-yl)-4-methyl phenyl-
methyl]acetamide 4b
o
White solid, m.p. 220-222 C, IR (KBr, vmax) 3380,
3261, 3063, 2975, 1680, 1568, 1548, 1460, 1050, 796 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.08 (s, Cph-CH3, 3H), 2.3
(s, COCH3, 3H), 6.59-7.19 (m, 6H), 7.32-7.38 (m, 2H),
7.63 (d, J = 8.3 Hz, 1H), 7.81-7.88 (m, 2H), 8.41 (d, J = 8.1
Hz, 1H), 9.78 (s, 1H). 13C NMR (22.5 MHz, DMSO-d6): d
21.09, 24.25, 43.28, 117.5, 118.6, 120.23, 121.71, 124.34,
125.65, 127.23, 128.50, 128.92, 129.27, 131.18, 131.28,
132.40, 134.05, 144.87, 154.93, 169.41.
EXPERIMENTAL
All the reactions were carried out using a conven-
tional (unmodified) a microwave oven (LG, 230 V, ~50
Hz). Reactions were monitored on TLC by comparison
with the samples prepared by known procedures. The IR
spectra were recorded using a Shimadzu 435-U-04 spectro-
photometer (KBr pellets) and the NMR spectra were ob-
tained in using a 90 MHz JEOL FT NMR spectrometer. All
melting points were determined on a Büchi 530 melting
point apparatus and are reported uncorrected.
General procedure for the preparation of amidoalkyl
naphthols
N-[(2-Hydroxynaphthlen-1-yl)-2-meth-yl phenyl-
methyl]acetamide 4c
o
White solid, m.p. 201-203 C, IR (KBr, vmax) 3385,
3263, 3058, 2933, 1679, 1570, 1542, 1509, 1316, 1050,
827 cm-1. 1H NMR (90 MHz, DMSO-d6): d 1.98 (s, Cph-
CH3, 3H), 2.24 (s, COCH3, 3H), 6.48-7.23 (m, 7H), 7.61-
7.78 (m, 4H), 8.39 (d, J = 8.0 Hz, 1H), 9.83 (s, 1H). 13C
NMR (22.5 MHz, DMSO-d6): d 20.71, 23.95, 42.69,
117.27, 119.01, 120.17, 123.5, 124.9, 126.34, 127.44,
128.12, 128.37, 128.75, 129.20, 130.83, 132.58, 135.54,
Method A:
A mixture of aldehyde (1 mmol), naphthalene-2-ol (1
mmol), acetamide (1.2 mmol) and DBH (0.11 mmol, 0.27
mg) were stirred at 100 oC in oil bath. The completion of
the reaction was monitored through TLC (ethyl ace-
J. Chin. Chem. Soc. 2012, 59, 193-198
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.jccs.wiley-vch.de
195

Article
Habibzadeh and Ghasemnejad-bosra
139.32, 155.18, 169.15.
155.81, 168.72.
N-[(2-Hydroxynaphthlen-1-yl)-4-nitro phenyl-methyl]
N-[(2-Hydroxynaphthlen-1-yl)-4-meth-oxy phenyl-
methyl]acetamide 4d
acetamide 4h
Yellow solid, m.p. 249-251 oC, IR (KBr, vmax) 3377,
3261, 3090, 1679, 1571, 1545, 1458, 1090, 838 cm-1. 1H
NMR (90 MHz, DMSO-d6): d 2.05 (s, CH3, 3H), 7.15-7.33
(m, 4H), 7.58-7.67 (m, 2H), 7.74 (d, J = 8.9 Hz, 2H), 7.90-
8.01 (m, 3H), 8.50 (d, J = 8.0 Hz, 1H), 9.82 (s, 1H); 13C
NMR (22.5 MHz, DMSO-d6): d 23.12, 47.18, 118.21,
119.47, 121.38, 122.44, 123.10, 127.23, 128.45, 128.73,
129.81, 131.56, 132.12, 133.02, 133.69, 144.14, 149.01,
152.03 , 168.90.
o
Pale yellow, m.p. 186-188 C, IR (KBr, vmax) 3375,
3252, 3070, 1692, 1566, 1549, 1509, 1448, 1250, 1108,
770 cm-1. 1H NMR (90 MHz, DMSO-d6): d 2.03 (s, CH3,
3H), 3.62 (s, OCH3,3H), 6.64 (d, J = 8.0 Hz, CHph, 2H),
6.69 (s, -CH-NH, 1H), 7.37-7.48 (m, 3H), 7.57 (t, J = 7.3
Hz, 2H), 7.75-7.81 (m, 2H), 8.32 (d, J = 8.2 Hz, 2H), 9.48
(s, 1H); 13C NMR (22.5 MHz, DMSO-d6): d 23.21, 42.49,
56.11, 114.14 117.65, 118.01, 122.82, 124.31, 126.80,
128.88, 128.97, 129.23, 131.10, 131.44, 132.21 133.52,
141.85, 154.08 , 159.87, 169.12.
N-[(2-Hydroxynaphthlen-1-yl)-3-nitro phenyl-methyl]
acetamide 4i
N-[(2-Hydroxynaphthlen-1-yl)-2-meth-oxy phenyl-
methyl]acetamide 4e
o
Pale yellow, m.p. 235-237 C, IR (KBr, vmax) 3374,
3241, 3110, 1691, 1575, 1546, 1451, 1100, 840 cm-1. 1H
NMR (90 MHz, DMSO-d6): d 2.12 (s, CH3, 3H), 7.14-7.45
(m, 6H), 7.76-8.02 (m, 5H), 8.53 (d, J = 8.1 Hz, 1H), 10.16
(s, 1H); 13C NMR (22.5 MHz, DMSO-d6): d 23.30, 48.15,
118.62, 118.79, 120.54, 122.37, 123.83, 125.75, 127.30,
128.46, 129.11, 129.64, 130.82, 133.12, 134.17, 144.58,
149.14, 152.28, 169.80.
o
White solid, m.p. 202-204 C, IR (KBr, vmax) 3384,
3265, 3080, 1682, 1568, 1544, 1442, 1238, 1025, 785 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.06 (s, CH3, 3H), 3.61 (s,
OCH3, 3H), 6.73 (s, -CH-NH, 1H), 6.95-7.34 (m, 7H),
7.70-7.78 (m, 2H), 8.07-8.10 (m, 2H), 9.84 (s, 1H); 13C
NMR (22.5 MHz, DMSO-d6): d 23.35, 40.01, 55.02,
116.21, 117.28, 118.25, 120.51, 122.60, 123.86, 127.07,
128.42, 128.63, 129.29, 131.24, 131.97, 135.14, 140.42,
157.91, 158.34, 168.01.
N-[(2-Hydroxynaphthlen-1-yl)-2-nitro phenyl-methyl]
acetamide 4j
o
Pale yellow, m.p. 178-180 C, IR (KBr, vmax) 3369,
N-[(2-Hydroxynaphthlen-1-yl)-3,4-di-methoxy phenyl-
methyl]acetamide 4f
3238, 3105, 1684, 1574, 1543, 1450, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.02 (s, CH3, 3H), 7.12-
7.42 (m, 5H), 7.71-7.83 (m, 4H), 7.92 (d, J = 8.1 Hz, 1H),
8.05 (d, J = 8.3 Hz, 1H), 8.52 (d, J = 8.2 Hz, 1H), 9.69 (s,
1H); 13C NMR (22.5 MHz, DMSO-d6): d 22.82, 48.01,
117.13, 118.42, 121.31, 123.49, 124.50, 126.54, 127.33,
128.25, 128.51, 129.38, 132.27, 133.01, 133.91, 144.14,
148.61, 152.14 , 169.21.
o
Pale yellow, m.p. 233-235 C, IR (KBr, vmax) 3371,
3250, 3085, 1689, 1565, 1542, 1437, 1245, 1062, 788 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.08 (s, CH3, 3H), 3.73 (s,
OCH3, 3H), 4.05 (s, OCH3, 3H), 6.72-6.83 (m, 2H), 7.97-
8.48 (m, 7H), 7.95-8.11 (m, 2H), 9.76 (s, 1H); 13C NMR
(22.5 MHz, DMSO-d6): d 22.06, 42.56, 56.01, 56.68,
113.92, 116.82, 119.83, 121.31, 122.80, 124.47, 126.77,
127.65, 127.84, 128.48, 131.76, 135.34, 138.97, 151.04,
153.01, 153.42, 168.77.
N-[(2-Hydroxynaphthlen-1-yl)-4-chloro phenyl-methyl]
acetamide 4k
o
Pale yellow, m.p. 222-224 C, IR (KBr, vmax) 3382,
3265, 3105, 1690, 1570, 1541, 1453, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.05 (s, CH3, 3H), 7.11
(m, 2H), 7.13-7.20 (m, 5H), 7.65-7.74 (m, 3H), 7.97 (d, J =
7.3 Hz, 1H), 8.12 (d, J = 7.1 Hz, 1H), 9.93 (s, 1H); 13C
NMR (22.5 MHz, DMSO-d6): d 23.21, 47.69, 118.31,
119.82, 122.14, 123,74, 125.83, 126.90, 127.34, 128.69,
129.27, 131.54, 132.01, 132.87, 134.14, 136.89, 142.53,
151.98, 169.80.
N-[(2-Hydroxynaphthlen-1-yl)-4-N,N-dimethyl phenyl-
methyl]acetamide 4g
o
Pale yellow, m.p. 126-127 C, IR (KBr, vmax) 3370,
3248, 3100, 1690, 1573, 1546, 1450, 1248, 1055, 792 cm-1.
1H NMR (90 MHz, DMSO-d6): d 1.99 (s, CH3, 3H), 3.02 (s,
CH3, 6H), 6.65 (s, -CH-NH, 1H), 6.71 (d, J = 8.3 Hz, 2H),
6.98-7.12 (m, 4H), 7.45-7.66 (m, 3H), 8.04 (d, J = 8.1 Hz,
1H), 8.43 (d, J = 8.2 Hz, 1H), 9.75 (s, 1H); 13C NMR (22.5
MHz, DMSO-d6): d 23.23, 39.82, 42.89, 113.81, 117.40,
118.77, 121.63, 123.38, 126.97, 127.81, 128.15, 128.72,
129.05, 130.0, 131.7, 133.8, 137.57, 140.42, 148.43,
N-[(2-Hydroxynaphthlen-1-yl)-2-chloro phenyl-methyl]
acetamide 4l
o
White solid, m.p. 196-198 C, IR (KBr, vmax) 3379,
196
www.jccs.wiley-vch.de
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2012, 59, 193-198

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Synthesis of 1-Amidoalkyl-2-naphthols by MW under Solvent Free
3255, 3105, 1693, 1572, 1545, 1458, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.03 (s, CH3, 3H), 6.97-
6.43 (m, 8H), 7.67-7.75 (m, 2H), 8.16-8.24 (m, 2H), 9.66
(s, 1H); 13C NMR (22.5 MHz, DMSO-d6): d 22.53, 47.32,
118.21, 123.50, 124.54, 126.97, 127.81, 127.92, 128.67,
129.19, 129.65, 130.21, 130.90, 131.84, 131.96, 136.173,
142.105, 151.33, 169.74.
2. Ugi, I. Adv. Synth. Catal. 1997, 339, 499.
3. Terret, N. K.; Gardener, M.; Gordon, D. W.; Kobylecki, R. J.;
Steele, J. Tetrahedron 1995, 51, 8135.
4. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
5. Domling, A. Chem. Rev. 2006, 106, 17.
6. Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun.
1997, 2015.
7. Wang, Y.-F.; Izawa, T.; Kobayashi, S.; Ohno, M. J. Am.
Chem. Soc. 1982, 104, 6465.
N-[(2-Hydroxynaphthlen-1-yl)-4-bromo phenyl-
methyl]acetamide 4m
8. Knapp, S. Chem. Rev. 1995, 95, 1859.
o
White solid, m.p. 228-230 C, IR (KBr, vmax) 3384,
9. Juaristi, E. Enantioselective Synthesis of b-Amino Acids;
John Wiley & Sons: New York, 1997.
3262, 3105, 1693, 1573, 1542, 1454, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 1.97 (s, CH3, 3H), 6.98-
7.34 (m, 8H), 7.61-7.65 (m, 2H), 7.87 (d, J = 7.9 Hz, 1H),
8.28 (d, J = 8.1 Hz, 1H), 9.74 (s, 1H); 13C NMR (22.5 MHz,
DMSO-d6): d 23.70, 46.58, 117.81, 118.78, 121.20,
122.43, 123.84, 126.95, 128.42, 128.78, 129.31, 130.25,
131.06, 131.94, 133.21, 129.23, 140.11, 150.69 , 168.41.
N-[(2-Hydroxynaphthlen-1-yl)-4-fluoro phenyl-methyl]
acetamide 4n
10. Szatmari, I.; Fülop, F. Curr. Org. Synth. 2004, 1, 155.
11. Shen, A. Y.; Tsai, C. T.; Chen, C. L. Eur. J. Med. Chem. 1999,
34, 877.
12. Khodaei, M. M.; Khosropour, A. R.; Moghanian, H. Synlett
2006, 916.
13. Kantevari, S.; Vuppalapati, S. V. N.; Nagarapu, L. Catal.
Commun. 2007, 8, 1857.
14. Selvam, N. P.; Perumal, P. T. Tetrahedron Lett. 2006, 47,
7481.
o
White solid, m.p. 202-203 C, IR (KBr, vmax) 3381,
15. Das, B.; Laxminarayana, K.; Ravikanth, B.; Rao, R. J. Mol.
Catal., A 2007, 261, 180.
3268, 3105, 1691, 1577, 1544, 1451, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 2.06 (s, CH3, 3H), 7.13
(m, 2H), 7.17-7.34 (m, 5H), 7.68-7.75 (m, 4H), 8.45 (d, J =
8.3 Hz, 1H), 9.86 (s, 1H); 13C NMR (22.5 MHz, DMSO-
d6): d 23.59, 47.10, 115.12, 117.91, 118.31, 121.42,
123.08, 126.17, 127.54, 128.04, 128.39, 128.90, 129.62,
130.9, 133.87, 137.39, 141.41, 151.33, 168.05.
16. Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Bioorg. Med.
Chem. Lett. 2008, 18, 788.
17. Su, W. K.; Tang, W. Y.; Li, J. J. J. Chem. Res. 2008, 123.
18. Nagarapu, L.; Baseeruddin, M.; Apuri, S.; Kantevari, S.
Catal. Commun. 2007, 8, 1729.
19. Nagawade, R. R.; Shinde, D. B. Chin. J. Chem. 2007, 25,
1710.
N-[(2-Hydroxynaphthlen-1-yl)-2,4-di-chloro phenyl-
methyl]acetamide 4o
20. Patil, S. B.; Singh, P. R.; Surpur, M. P.; Samant, S. D.
Ultrason. Sonochem. 2007, 14, 515.
o
White solid, m.p. 199-101 C, IR (KBr, vmax) 3380,
21. Jiang, W.-Q.; An, L.-T.; Zou, J.-P. Chin. J. Chem. 2008, 26,
697.
3266, 3105, 1701, 1574, 1547, 1459, 1235, 1039, 770 cm-1.
1H NMR (90 MHz, DMSO-d6): d 1.97 (s, CH3, 3H), 6.97-
7.15 (m, 2H), 7.26-7.38 (m, 4H), 7.59 (d, J = 8.0 Hz, 1H),
7.72-7.78 (m, 2H), 7.96 (d, J = 8.2 Hz, 1H), 7.65 (d, 1H),
9.87 (s, 1H); 13C NMR (22.5 MHz, DMSO-d6): d 23.12,
48.40, 117.25, 118.64, 122.81, 123.23, 127.65, 129.44,
129.81, 130.29, 131.42, 132.51, 132.90, 133.43, 134.14,
136.87, 139.01, 150.29, 168.65.
22. Patil, S. B.; Singh, P. R.; Surpur, M. P.; Samant, S. D. Synth.
Commun. 2007, 37, 1659.
23. Srihari, G.; Nagaraju, M.; Murthy, M. M. Helv. Chim. Acta.
2007, 90, 1497.
24. Hajipour, A. R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A. E. Tet-
rahedron Lett. 2009, 50, 5649.
25. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic
Chemistry; University Science Books: Sausalito, California,
2006.
ACKNOWLEDGEMENTS
26. Ghasemnejad-Bosra, H.; Faraje, M.; Habibzadeh, S.;
Ramzaniyan-Lehmali, F. J. Serb. Chem. Soc. 2010, 75, 299.
27. Azarifar, D.; Ghasemnejad-Bosra, H.; Zolfigol, M. A.;
Tajbaksh, M. Heterocycles 2006, 68, 175.
28. Azarifar, D.; Ghasemnejad-Bosra, H. Synthesis 2006, 1123.
29. Azarifar, D.; Ghasemnejad Bosra, H.; Tajbaksh, M. J.
Heterocycl. Chem. 2007, 44, 467.
We wish to thank the Industrial Noshiravani Univer-
sity, Babol, Iran, for financial support during the realiza-
tion of this research
REFERENCES
1. Strecker, A. Liebigs Ann. Chem. 1850, 75, 27.
J. Chin. Chem. Soc. 2012, 59, 193-198
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.jccs.wiley-vch.de
197

Article
Habibzadeh and Ghasemnejad-bosra
30. Ghasemnejad-Bosra, H.; Haghdadi, M.; Gholampour-Azizi,
I. Heterocycles 2008, 75, 391.
33. Habibzadeh, S.; Ghasemnejad-Bosra, H.; Faraji, M. Helv.
Chim. Acta. 2011, 94, 429.
31. Ghasemnejad-Bosra, H.; Haghdadi, M.; Khanmohamadi, O.;
Gholipour, M.; Asghari, G. J. Chin. Chem. Soc. 2008, 55,
464.
34. Khazaei, A.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Zare, A.;
Parhami, A.; Khalafi-Nezhad, A. Appl. Catal., A 2010, 386,
179.
32. Ghasemnejad-Bosra, H.; Faraje, M.; Habibzadeh, S. Helv.
Chim. Acta 2009, 92, 575.
35. Nandi, G. Ch.; Samai, S.; Kumar, R.; Singh. M. S. Tetrahe-
dron Lett. 2009, 50, 7220.
198
www.jccs.wiley-vch.de
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2012, 59, 193-198