Strontium(II) triflate catalysed condensation of β-naphthol, aldehyde and urea or amides: A facile synthesis of amidoalkyl naphthols

Article abstract of DOI:10.3184/030823408X298508

A novel and efficient synthesis of amidoalkyl naphthols has been developed by one-pot condensation of β-naphthol, aromatic aldehydes and urea or amides in the presence of strontium(II) triflate as a catalyst in high yields.

Full text of DOI:10.3184/030823408X298508

JOURNAL OF CHEMICAL RESEARCH 2008
MARCH, 123–128
RESEARCH PAPER 123
Strontium(II) triflate catalysed condensation of β-naphthol, aldehyde and
urea or amides: a facile synthesis of amidoalkyl naphthols
Weike Su*, Wenyuan Tang and Jianjun Li
College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering,
Hangzhou, 310014, P.R. China
A novel and efficient synthesis of amidoalkyl naphthols has been developed by one-pot condensation of b-naphthol,
aromatic aldehydes and urea or amides in the presence of strontium(II) triflate as a catalyst in high yields.
Key words: strontium(II) triflate, one-pot reaction, condensation, amidoalkyl naphthol, β-naphthol
Naphthalene derivatives have attracted considerable interest
because of their pharmaceutical and agricultural activities.1-10
For example, naphazoline and pronethalol have been reported
to act as cardiovascular agents.6 1-naphthaleneacetic acid and
2-naphthoxyacetic acid have been reported to act as plant
growth regulators.7,8 Whilst, 2-naphthol and its derivatatives
have also been reported as bactericides9 and antioxidants.10
Furthermore, many chiral amidoalkyl phenols have been
reported as excellent chelating agents for metal-catalysed
asymmetric synthesis.11-15 Particulary, chiral Mannich bases
of β-naphthol are commonly used as metal-mediated and
ligand-accelerated catalysts in enantioselective carbon–carbon
bond formation.16-21
Various methods have been reported for the aminoalkylation
of β-naphthol, with aromatic aldehydes and heterocyclic
amines,22,23 pyrrolidine,24 iminium salts25,26 and methyl
carbamate.27 However, to the best of our knowledge, there
have been only a few reports of the synthesis of amidoalkyl
naphthols in the presence of urea or amides.28,29 Recently,
Khodaei disclosed that the condensation of β-naphthol,
aromatic aldehydes and urea or amides in the presence of
p-toluenesulfonic acid, afforded amidoalkyl naphthols.28
Patil and co-workers used indion-130 for the synthesis of
these compounds.29 However, these methodologies have
some limitations such as prolonged reaction times, special
apparatus, and the use of environmentally unfriendly catalysts
and harsh reaction conditions. The challenge for a sustainable
environment calls for clean procedures that can avoid using
harmful catalysts. Therefore, the need for a new, simple, green,
one-pot methods for the synthesis of amidoalkyl naphthols is
highly desirable.
Table1 Catalysteffectonthecondensationreactionof4-chloro-
benzaldehyde, b-naphthol and urea
Entry
Catalyst
Catalyst/mol%
Time/h
Yield/%b
1
2
3
4
5
6
7
8
9a
Y(OTf)3
10
10
10
10
10
10
10
10
10
12
12
12
12
12
12
12
12
12
-
-
-
<10
<10
15
Eu(OTf)3
Mg(OTf)2
Yb(OTf)3
Zn(OTf)2
Cu(OTf)2
Bi(OTf)3
Sc(OTf)3
Sr(OTf)2
30
35
85, 87,
85, 85, 84
28
10
11
12
Sr(OTf)2
Sr(OTf)2
Sr(OTf)2
1
5
15
12
12
12
70
84
aCatalyst was reused five times.
bIsolated yield.
applied metal triflates to several reactions.35-37 However, up to
now, Sr(OTf)2 has seldom been studied as a catalyst. We have
also reported a simple, efficient and practical procedure for
the MCRs such as one-pot synthesis of dihydropyrimidones
catalysed by strontium(II) triflate.38
In continuation of our previous work on metal triflate
catalysed MCRs, we report a simple, efficient and practical
procedures for the synthesis of amidoalkyl naphthols using
Sr(OTf)239 as the catalyst in chloroform (Scheme 1).
Initially, we investigated the amidoalkylation of β-naphthol,
4-chlorobenzaldehyde and urea using metal triflates as catalyst
at reflux temperature in chloroform and the results are listed in
Table 1. It was found that all metal triflates showed catalytic
effects except Y(OTf)3, Eu(OTf)3 and Mg(OTf)2 (Table 1,
entries 1–3). Most excitingly, when Sr(OTf)2 was used, the
reaction proceeded smoothly and gave the product in 85%
yield (Table 1, entry 9). Moreover, we found that the yields
were obviously affected by different amounts of Sr(OTf)2.
When using 1%, 5%, 10% and 15% of Sr(OTf)2, the yields
were 28%, 70%, 85% and 84% respectively (Table 1, entries
9–12). Therefore, 10% of Sr(OTf)2 was sufficient and excess
amount of catalyst did not increase the yields significantly
(Table 1, entries 9–12). The activity of the recycled Sr(OTf)2
was also examined. In this reaction, Sr(OTf)2 could be reused
Multicomponent reactions (MCRs) have attracted
considerable attention due to the fact that the products
are formed in a single step without the need to isolate any
intermediate. Diversity can be achieved simply by varying
the reacting components and also complex molecules can be
built up.30-33 Thus, development and discovery of new MCRs
is of interest.
In recent years, rare earth metal triflate salts have been
widely used in organic synthesis due to their low toxicity,
low cost, high stability, ease of handling, water tolerance and
ease of recovery from water.34 Recently, we have successfully
O
O
Sr(OTf)2 (10 mol%)
OH
+
+
R1
NH2
R2
H
CHCl3, reflux
OH
2
R2
NHCOR1
1
3
Scheme 1
* Correspondent. E-mail: suweike@zjut.edu.cn
PAPER: 08/5086

124 JOURNAL OF CHEMICAL RESEARCH 2008
Table2 Solventeffectonthereactionof4-chlorobenzaldehyde,
b-naphthol and urea catalysed by Sr(OTf)2
The reaction could be carried out under solvent-free condition
at 120°C in 75% yield (Table 2, entry 9). Most excitingly,
when chloroform was used as solvent at reflux temperature,
the yield increased to 85% (Table 2, entry 1) which was better
than any other solvents.
In order to study the generality of this procedure, a series
of aldehydes and urea or amides were used. The results are
shown in Table 3. The three component condensation reaction
proceeded smoothly in chloroform at reflux temperature
and were complete in 12 h. The reactions of aldehydes
with β-naphthol and urea or different amides provided the
corresponding amidoalkyl naphthols in good to excellent
yields (Table 3).
In all case, aromatic aldehydes with substituents bearing
either electron-donating or electron-withdrawing groups
reacted successfully and gave the products in good yields.
However, the substituents on the aromatic ring have an
influence on the reaction. Aromatic rings bearing electron-
withdrawing groups required a shorter time and gave higher
yields (Table 3).
The condensation reactions of aromatic aldehydes,
β-naphthol with urea gave the corresponding products in
good yields. As compared to the urea, we studied that the
reactions of aromatic aldehydes with β-naphthol and different
amides, including acetamide, benzamide, propenionamide
and thiophene-2-carboxamide under similar conditions.
All the amides afforded the corresponding amidoalkyl
naphthols in higher yields than urea. Furthermore, amidoalkyl
naphthols were the sole products and no by-product was
observed (Table 3).
Entry
Solvent
Time/h
Yield/%a
1
2
3
4
5
6
7
8
9
CHCl3
12
12
12
12
12
12
12
12
12
85
77b, 78c
<30
ClCH2CH2Cl
MeCN
CH3NO2
EtOH
78d, 79e, 65f
<30
THF
H2O
[bpy]BF4
None
<10
-
46
75g
aIsolated yield.
bReaction conditions: 2 ml ClCH2CH2Cl at 60°C; cReaction
conditions: 2 ml ClCH2CH2Cl at 80°C; dReaction conditions:
2 ml CH3NO2 at 60°C; eReaction conditions: 2 ml CH3NO2 at
f
80°C; Reaction conditions: 2 ml CH3NO2 at 100°C; gReaction
conditions: solvent-free at 120°C.
five times without any loss of activity (Table 1, entry 9).
In addition, we studied the reaction with these catalysts
in chloroform at room temperature. It was found that the
reaction also gave the moderate yields but required much
longer reaction time for five days. When no catalyst was used,
no products were detected. Showing that Sr(OTf)2 played an
important role in this reaction. Thus our study showed the best
results were obtained when 10 mol% Sr(OTf)2 was used in
chloroform under reflux (Table 1, entry 9).
Then, we examined the above reaction in different solvents
at 60°C (Table 2). It was found that this condensation reaction
was affected by various solvents. The results indicated that
acetonitrile, ethanol, tetrahydrofuran and [bpy]BF4 are
unsuitable for the reaction. When H2O was used as solvent, no
products were detected. Solvents such as 1,2-dichloroethane
and nitromethane, proved to be effective. Different yields were
obtained at different temperatures (Table 2, entries 2 and 4).
On the basis of the above results, this process was then
extended to heterocyclic aldehyde and aliphatic aldehyde.
The corresponding products (3v, 3w) were obtained in 80%
and 91% yields, respectively (Table 3, entries 22 and 23).
Interestingly, when glutaraldehyde was used as the aldehyde
component and reacted with 2 equivalents of β-naphthol
Table 3 Synthesis of amidoalkyl naphthols in the presence of Sr(OTf)2
O
O
Sr(OTf)2 (10 mol%)
CHCl3, reflux
+
+
OH
R1
NH2
R2
H
OH
R2
NHCOR1
1
2
3
Entry
R1
R2
Product
Time/h
Yield/%a
1
2
NH2
NH2
NH2
NH2
NH2
C6H5
C6H5
C6H5
C6H5
C6H5
2-thiophene
2-thiophene
2-thiophene
2-thiophene
2-thiophene
CH3
p-(OCH3)C6H4
p-(CH3)C6H4
C6H5
p-(Cl)C6H4
m-(NO2)C6H4
p-(OCH3)C6H4
p-(CH3)C6H4
C6H5
p-(Cl)C6H4
m-(NO2)C6H4
p-(OCH3)C6H4
p-(CH3)C6H4
C6H5
p-(Cl)C6H4
m-(NO2)C6H4
p-(OCH3)C6H4
C6H5
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
3p
3q
3r
15
15
12
12
10
10
10
9
80
82
84
85
89
89
90
93
93
95
90
90
92
93
96
89
90
93
90
90
94
80
91
3
4
5
6
7
8
9
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
8
10
10
9
9
8
12
10
8
12
10
8
CH3
CH3
m-(NO2)C6H4
p-(OCH3)C6H4
C6H5
m-(NO2)C6H4
2-furyl
CH3CH2
CH2 =CH
CH2 =CH
CH2 =CH
C6H5
3s
3t
3u
3v
3w
15
10
C6H5
aIsolated yield.
PAPER: 08/5086

JOURNAL OF CHEMICAL RESEARCH 2008 125
Eq. 1
O
HO
OH
Sr(OTf)2 (10 mol%)
CHCl3, reflux, 15 h
NH2
+
+
OHC
CHO
OH
PhOCHN
NHCOPh
4% yield
2 equiv
1 equiv
2 equiv
4a
Eq. 2
HO
O
H
OH
O
Sr(OTf)2 (10 mol%)
CHCl3, reflux, 15 h
+
+
Ph
N
H
N
H
Ph
H2N
NH2
OH
O
1 equiv
2 equiv
2 equiv
58% yield
5a
Eq. 3
O
O
H
N
Ph
H
Sr(OTf)2 (10 mol%)
CHCl3, reflux, 12 h
NH2
+
+
OH
O
OH
NO2
1 equiv
NO2
60% yield
1 equiv
1 equiv
6a
Scheme 2
Mass spectra were measured with Thermo Finnigan LCQ-Advantage.
Elemental analysis was determined on a Carlo-Erba 1108 instrument.
and 2 equivalents of benzamide it gave the corresponding
diamidoalkylation product in only 4% yield (Scheme 2,
Eqn (1)). However, the reaction of urea was studied in a
diamidoalkylation reaction. The yield of the diamidoalkylation
product was 58% (Scheme 2, Eqn (2)), when the molar ratio
of aldehyde, β-naphthol and urea was 2:2:1. In addition, using
α-naphthol instead of β-naphthol, the desired product was also
obtained in moderate yield (Scheme 2, Eqn (3)).
A tentative mechanism for the formation of amidoalkyl
naphthols is proposed in Scheme 3. The reaction may proceed
viatheacyliminineintermediate. Referringtotheliterature,40-43
we supposed that an intermediate is formed by the reaction of
the aldehyde and urea by Sr(OTf)2. Subsequent addition of the
β-naphthol afforded the corresponding amidoalkyl naphthols
(Scheme 3).
General procedure for the synthesis of amidoalkyl naphthols 3a–3w
To a mixture of aldehyde (1 mmol), β-naphthol (1 mmol) and urea
or amide (1.1 mmol) was added Sr(OTf)2 (0.1 mmol, 10 mol%) in
chloroform (2 ml). The mixture was stirred at 60°C for the time as
shown in Table 3. The progress of the reaction was monitored by
TLC. After completion of the reaction, the mixture was filtered and
the precipitate washed with H2O. The crude products were purified
by recrystallisation from ethyl acetate and the pure products were
obtained in 80–96% yields.
General procedure for the synthesis of N,N’-(1,5-bis(2-
hydroxynaphthalen-1-yl)pentane-1,5-diyl)dibenzamide 4a
To a mixture of glutaraldehyde (1 mmol), β-naphthol (2 mmol)
and benzamide (2 mmol) was added Sr(OTf)2 (0.1 mmol, 10 mol%)
in chloroform (2 ml). The mixture was stirred at 60°C for 15 h. The
progress of the reaction was monitored by TLC. After completion of
the reaction, the mixture was filtered and the precipitate washed with
H2O. The crude product was purified by recrystallisation from ethyl
acetate and the pure product was obtained in 4% yields.
In summary, we have developed a novel catalytic approach
to the synthesis of amidoalkyl naphthols using strontium(II)
triflate. The method has several advantages including its high
yield, environmental suitability, simple work-up procedure
and the easy isolation of its products. Studies on the extension
of this protocol are ongoing in our laboratory.
General procedure for the synthesis of 1,3-bis((2-hydroxynaphthalen-
1-yl)(phenyl)methyl)urea 5a
Experimental
To a mixture of benzaldehyde (2 mmol), β-naphthol (2 mmol)
and urea (1 mmol) was added Sr(OTf)2 (0.1 mmol, 10 mol%) in
chloroform (2 ml). The mixture was stirred at 60°C for 15 h. The
progress of the reaction was monitored by TLC. After completion of
the reaction, the mixture was filtered and the precipitate washed with
H2O. The crude product was purified by recrystallisation from ethyl
acetate and the pure product was obtained in 58% yields.
Chemicals and solvents were either purchased or purified by standard
techniques. Melting points were determined on a Büchi B-540
melting apparatus and uncorrected. The NMR spectra were measured
with a Bruker Advance ΙΙΙ 500 or Varian Mercury Plus-400 instrument
using DMSO as the solvent with TMS as internal standard. IR spectra
were recorded using KBr pellets on a Nicolet Aviatar-370 instrument.
Sr(OTf)2
O
O
OH
OH
-H2O
(TfO)2Sr
R1CHO
N
R2
+
R2
NH2
1
R
NHCOR2
R1
H
Scheme 3
PAPER: 08/5086

126 JOURNAL OF CHEMICAL RESEARCH 2008
General procedure for the synthesis of N-((1-hydroxynaphthalen-2-
yl)(3-nitrophenyl)methyl)benzamide 6a
N-((2-hydroxynaphthalen-1-yl)(p-tolyl)methyl)benzamide
(3g):
White solid m.p. 216–217°C in 90% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.35 (1H, s, OH), 9.03 (1H, d, J = 8.4 Hz, NH), 8.10
(1H, d, J = 8.8 Hz, ArH), 7.89–7.79 (4H, m, ArH), 7.55–7.45 (4H, m,
ArH), 7.33–7.26 (3H, m, ArH), 7.20 (2H, d, J = 8.0 Hz, ArH), 7.09
(2H, d, J = 8.0 Hz, ArH), 2.24 (3H, s, CH3). 13C NMR (100 MHz,
DMSO-d6): 165.6, 153.1, 139.0, 135.6, 134.4, 132.3 (CH × 2),
131.3, 129.2 (CH × 4), 128.7 (CH × 2), 128.5 (CH × 2), 127.0, 126.7
(CH × 2), 126.4, 122.6, 118.7, 118.4, 49.1, 20.5. IR nmax (KBr):
3417, 1631, 1530, 1438, 1345, 817, 712, 586 cm-1. MS (ESI) m/z 368
([M-1]+, 100), 143 (23). Found: C, 81.65; H, 5.85; N, 3.79. Calc. for
C25H21NO2: C, 81.72; H, 5.76; N, 3.81%.
To
a mixture of 3-nitrobenzaldehyde (1 mmol), α-naphthol
(1 mmol) and benzamide (1.1 mmol) was added Sr(OTf)2 (0.1
mmol, 10 mol%) in chloroform (2 ml). The mixture was stirred at
60°C for 15 h. The progress of the reaction was monitored by TLC.
After completion of the reaction, water was added and the product
was extracted with ethyl acetate (3 × 10 ml). The organic layer was
dried ( MgSO4) and evaporated, and the crude product was purified
by flash chromatography (ethyl acetate/petroleum ether, 1:12 to 1:4)
to provide the corresponding product. The pure product was obtained
in 60% yield.
N-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)benzamide
(3h):
White solid m.p. 242–243°C in 93% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.34 (1H, s, OH), 9.03 (1H, d, J = 8.4 Hz, NH), 8.09
(1H, d, J = 8.8 Hz, ArH), 7.88–7.79 (4H, m, ArH), 7.57–7.45 (4H,
m, ArH), 7.33–7.19 (8H, m, ArH). 13C NMR (100 MHz, DMSO-
d6): 165.7, 153.1, 142.0, 134.3, 132.3, 131.4, 129.3 (CH × 2), 128.6
(CH × 2), 128.5 (CH × 2), 128.3, 128.1, 127.1 (CH × 2), 126.7, 126.5,
126.4, 122.6 (CH × 2), 118.7, 118.3, 49.2. IR nmax (KBr): 3419, 3061,
1631, 1435, 1348, 1272, 823, 697, 584 cm-1. MS (ESI) m/z 353 (M+,
5), 231(98). Found: C, 81.48; H, 5.55; N, 3.93. Calc. for C24H19NO2:
C, 81.56; H, 5.42; N, 3.96%.
N-((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)benzamide
(3i): White solid m.p. 187–188°C in 93% yield. 1H NMR (500 MHz,
DMSO-d6): δ 10.36 (1H, s, OH), 9.02 (1H, d, J = 8.5 Hz, NH), 8.06
(1H, d, J = 8.5 Hz, ArH), 7.88–7.80 (4H, m, ArH), 7.57–7.45 (4H,
m, ArH), 7.35–7.23 (7H, m, ArH). 13C NMR (125 MHz, DMSO-d6):
166.4, 153.7, 141.6, 134.7, 132.7, 132.0 (CH × 2), 131.6 (CH × 2),
130.1 (CH × 2), 129.1 (CH × 2), 128.9, 128.8, 128.6 (CH × 2), 127.7,
127.3, 123.2 (CH × 2), 119.1, 118.4, 49.2. IR nmax (KBr): 3420, 3182,
1630, 1514, 1401, 1340, 1267, 1093, 812, 725 cm-1. MS (ESI) m/z
386 ([M-1]+, 100), 143 (20). Found: C, 74.21; H, 4.79; N, 3.53. Calc.
for C24H18ClNO2: C, 74.32; H, 4.68; N, 3.61%.
N-((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)benzamide
(3j): White solid m.p. 241–242°C in 95% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.45 (1H, s, OH), 9.17 (1H, d, J = 8.0 Hz, NH), 8.14–
8.10 (3H, m, ArH), 7.93–7.85 (4H, m, ArH), 7.74 (1H, d, J = 8.0 Hz,
ArH), 7.62–7.55 (2H, m, ArH), 7.50 (3H, t, J = 7.6 Hz, ArH), 7.42
(1H, d, J = 8.0 Hz, ArH), 7.34 (1H, t, J = 7.2 Hz, ArH), 7.28 (1H,
d, J = 8.4 Hz, ArH). 13C NMR (100 MHz, DMSO-d6): 166.2, 153.4,
147.8, 144.5, 134.0, 133.2, 132.2 (CH × 2), 131.5, 129.9, 129.7,
128.7 (CH × 2), 128.4, 127.3, 127.0, 122.8, 122.5, 121.6 (CH × 2),
120.9, 118.6, 117.3, 48.9. IR nmax (KBr): 3377, 3266, 1633, 1530,
1347, 820, 733, 655 cm-1. MS (ESI) m/z 397 ([M-1]+, 100), 143(15).
Found: C, 72.26; H, 4.65; N, 6.96. Calc. for C24H18N2O4: C, 72.35;
H, 4.55; N, 7.03%.
Spectroscopic data for the products
1-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)urea (3a):
Yellow solid m.p. 99–100°C in 80% yield. 1H NMR (400 MHz,
DMSO-d6): δ 9.95 (1H, s, OH), 7.82–7.73 (2H, m, ArH), 7.40 (1H, s,
NH), 7.29–7.19 (2H, m, ArH), 7.09–7.06 (2H, m, ArH), 6.89 (2H, s),
6.80 (2H, d, J = 8.4 Hz, ArH), 5.82 (2H, s, NH2), 3.68 (3H, s, OCH3).
13C NMR (100 MHz, DMSO-d6): 158.6, 157.5, 152.9, 136.1, 132.3,
128.8 (CH × 2), 128.6 (CH × 3), 127.0, 126.4, 122.4, 120.3, 118.6,
113.3 (CH × 2), 55.0, 47.8. IR nmax (KBr): 3472, 3367, 1662, 1510,
1250, 1177, 1033, 815, 746, 595 cm-1. MS (ESI) m/z 321 ([M-1]+,
100). Found: C, 70.60; H, 5.79; N, 8.53. Calc. for C19H18N2O3: C,
70.79; H, 5.63; N, 8.69%.
1-((2-hydroxynaphthalen-1-yl)(p-tolyl)methyl)urea (3b): Yellow
solid m.p. 117–118°C in 82% yield. 1H NMR (400 MHz, DMSO-d6):
δ9.92(1H, s, OH), 7.81(1H, d, J=8.0Hz,ArH), 7.74(1H, d, J=8.8Hz,
ArH), 7.39 (1H, s, NH), 7.26 (1H, t, J = 7.6 Hz, ArH), 7.20 (1H, d,
J = 9.2 Hz, ArH), 7.06–7.01 (4H, m, ArH), 6.89 (2H, s), 5.81 (2H, s,
NH2), 2.22 (3H, s, CH3). 13C NMR (100 MHz, DMSO-d6): 158.6,
152.9, 141.3, 134.7, 132.3, 128.9 (CH × 2), 128.6, 128.5 (CH × 4),
125.8, 122.4 (CH × 2), 120.4, 118.6, 47.8, 20.6. IR nmax (KBr): 3468,
3386, 1650, 1514, 1439, 1356, 1268, 813, 746 cm-1. MS (ESI) m/z
306 (M+, 5), 231 (48), 144 (98). Found: C, 74.33; H, 6.05; N, 9.06.
Calc. for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14%.
1-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)urea (3c): White
solid m.p. 174–175°C in 84% yield. 1H NMR (400 MHz, DMSO-d6):
δ 9.97 (1H, s, OH), 7.83–7.75 (3H, m, ArH), 7.40 (1H, s, NH), 7.29–
7.11 (7H, m, ArH), 6.94 (2H, s), 5.86 (2H, s, NH2). 13C NMR (100
MHz, DMSO-d6): 158.5, 152.8, 144.3, 128.9, 128.6 (CH × 2), 127.8,
126.4 (CH × 4), 125.8 (CH × 2), 122.4 (CH × 2), 120.2, 118.5, 48.1.
IR nmax (KBr): 3464, 3346, 3217, 1664, 1535, 1438, 1356, 1270, 813,
745, 699 cm-1. MS (ESI) m/z 291 ([M-1]+, 60), 248 (98), 215 (80),
143 (33). Found: C, 73.86; H, 5.66; N, 9.50. Calc. for C18H16N2O2:
C, 73.95; H, 5.52; N, 9.58%.
1-((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)urea (3d):
White solid m.p. 115–116°C in 85% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.00 (1H, s, OH), 7.83–7.76 (3H, m, ArH), 7.43 (1H,
s, NH), 7.31–7.14 (6H, m, ArH), 6.90 (2H, s), 5.86 (2H, s, NH2).
13C NMR (100 MHz, DMSO-d6): 158.6, 152.9, 148.9, 143.5, 132.1
(CH × 2), 131.6, 130.4 (CH × 4), 129.2, 128.7, 127.8, 127.7, 122.5,
118.5, 47.7. IR nmax (KBr): 3483, 3380, 3180, 1654, 1600, 1518,
1439, 1357, 1268, 815, 752 cm-1. MS (ESI) m/z 326 (M+, 5), 265
(49), 231 (98), 144 (95). Found: C, 66.06; H, 4.78; N, 8.49. Calc. for
C18H15ClN2O2: C, 66.16; H, 4.63; N, 8.57%.
N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)thiophene-
2-carboxamide (3k): Yellow solid m.p. 119–120°C in 90% yield.
1H NMR (400 MHz, DMSO-d6): δ 10.24 (1H, s, OH), 8.94 (1H, d,
J = 8.4 Hz, NH), 8.03 (1H, d, J = 8.8 Hz, ArH), 7.86–7.76 (4H, m,
ArH), 7.43 (1H, t, J = 8.0 Hz, ArH), 7.31–7.13 (6H, m, ArH), 6.84
(2H, d, J = 8.4 Hz, ArH), 3.69 (3H, s, CH3). 13C NMR (100 MHz,
DMSO-d6): 160.5, 158.1, 153.2, 139.4 (CH × 2), 133.6, 132.3, 131.0,
129.3 (CH × 2), 128.6, 128.4, 128.0, 127.9, 126.6, 122.9, 122.6, 118.7,
118.2, 113.6 (CH × 2), 55.1, 48.9. IR nmax (KBr): 3406, 1624, 1536,
1511, 1249, 1177, 816, 745 cm-1. MS (ESI) m/z 388 ([M-1]+, 100).
Found: C, 70.81; H, 5.03; N, 3.53; S, 8.14. Calc. for C23H19NO3S: C,
70.93; H, 4.92; N, 3.60; S, 8.23%.
N-((2-hydroxynaphthalen-1-yl)(p-tolyl)methyl)thiophene-2-
carboxamide (3l): White solid m.p. 206–207°C in 90% yield.
1H NMR (400 MHz, DMSO-d6): δ 10.27 (1H, s, OH), 8.97 (1H, d,
J = 8.8 Hz, NH), 8.04 (1H, d, J = 8.8 Hz, ArH), 7.90–7.76 (4H, m,
ArH), 7.44 (1H, t, J = 8.0 Hz, ArH), 7.31–7.14 (6H, m, ArH), 7.09
(2H, d, J = 8.0 Hz, ArH), 2.24 (3H, s, CH3). 13C NMR (100 MHz,
DMSO-d6): 160.5, 153.2, 139.3, 138.7 (CH × 2), 135.6, 132.3, 131.0
(CH × 2), 129.3 (CH × 2), 128.7, 128.5, 128.4 (CH × 2), 127.9, 126.5,
122.5 (CH × 2), 118.6, 118.2, 49.0, 20.5. IR nmax (KBr): 3387, 3186,
1628, 1536, 814, 722 cm-1. MS (ESI) m/z 372 ([M-1]+, 30), 143 (5).
Found: C, 73.85; H, 5.26; N, 3.69; S, 8.70. Calc. for C23H19NO2S: C,
73.97; H, 5.13; N, 3.75; S, 8.59%.
1-((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)urea
(3e):
Yellow solid m.p. 179–180°C in 89% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.13 (1H, s, OH), 8.09–7.99 (2H, m), 7.87–7.46 (7H,
m), 7.33–7.21 (2H, m), 7.12 (1H, d, J = 8.4 Hz), 7.06–6.99 (1H, m),
5.96 (1H, s). 13C NMR (100 MHz, DMSO-d6): 158.5, 153.0, 147.7,
147.1, 132.6, 132.0, 129.6, 129.5, 128.7, 128.3, 126.9, 122.6, 121.0
(CH × 2), 120.2, 119.1, 118.4, 48.4. IR nmax (KBr): 3479, 3396, 1651,
1528, 1348, 1268, 813, 748 cm-1. MS (ESI) m/z 336 ([M-1]+, 100),
293 (40). Found: C, 64.01; H, 4.59; N, 12.37. Calc. for C18H15N3O4:
C, 64.09; H, 4.48; N, 12.46%.
N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)benzamide
(3f): White solid m.p. 208–209°C in 89% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.36 (1H, s, OH), 9.05 (1H, d, J = 8.4 Hz, NH), 8.09
(1H, d, J = 8.4 Hz, ArH), 7.87–7.79 (4H, m, ArH), 7.55–7.48 (4H, m,
ArH), 7.33–7.23 (5H, m, ArH), 6.85 (2H, d, J = 8.4 Hz, ArH), 3.69
(3H, s, CH3). 13C NMR (100 MHz, DMSO-d6): 153.0, 134.4, 133.9,
132.2, 131.4, 129.2 (CH × 4), 128.5 (CH × 3), 127.7 (CH × 2), 127.0
(CH × 2), 126.7 (CH × 2), 122.6 (CH × 2), 118.7, 113.6 (CH × 2),
55.0, 48.9. IR nmax (KBr): 3422, 3065, 1630, 1511, 1437, 1345, 1262,
1171, 1029, 826, 712, 589 cm-1. MS (ESI) m/z 382 ([M-1]+, 100),
143 (20). Found: C, 78.22; H, 5.65; N, 3.53. Calc. for C25H21NO3: C,
78.31; H, 5.52; N, 3.65%.
N-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)thiophene-2-
carboxamide (3m): White solid m.p. 220–221°C in 92% yield.
1H NMR (400 MHz, DMSO-d6): δ 10.24 (1H, s, OH), 8.96 (1H, d,
J = 8.4 Hz, NH), 8.04 (1H, d, J = 8.4 Hz, ArH), 7.90–7.77 (4H, m,
ArH), 7.44 (1H, t, J = 7.6 Hz, ArH), 7.32–7.14 (9H, m, ArH). 13C
NMR (100 MHz, DMSO-d6): 160.7, 153.3, 141.7, 139.3 (CH × 2),
132.4, 131.1, 129.4 (CH × 2), 128.6, 128.4 (CH × 2), 128.2 (CH × 2),
128.0, 126.6, 122.9, 122.6 (CH × 2), 118.6, 118.1, 49.2. IR nmax
PAPER: 08/5086

JOURNAL OF CHEMICAL RESEARCH 2008 127
(KBr): 414, 1620, 1536, 1357, 1057, 820, 719 cm-1. MS (ESI) m/z
358 ([M-1]+, 25), 143 (3). Found: C, 73.35; H, 4.90; N, 3.83; S, 8.90.
Calc. for C22H17NO2S: C, 73.51; H, 4.77; N, 3.90; S, 8.92%.
J1 = 17.2 Hz, J2 = 2.0 Hz,:CH2), 5.61 (1H, dd, J1 = 10.4 Hz, J2 = 2.0 Hz,:
CH2). 13C NMR (100 MHz, DMSO-d6): 164.5, 153.2, 142.2, 132.3,
131.8, 129.3 (CH × 2), 128.5, 128.4, 128.0, 126.3, 126.2, 126.1,
125.6, 123.2, 122.4 (CH × 2), 118.5, 118.4, 48.1. IR nmax (KBr):
3398, 3067, 1655, 1515, 1438, 1339, 1270, 1069, 744, 650 cm-1.
MS (ESI) m/z 302 ([M-1]+, 70), 195 (100), 143 (10). Found: C, 79.10;
H, 5.73; N, 4.59. Calc. for C20H17NO2: C, 79.19; H, 5.65; N, 4.62%.
N-((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)acrylamide
(3u): Yellow solid m.p. 247–248°C in 94% yield. 1H NMR
(400 MHz, DMSO-d6): δ 10.20 (1H, s, OH), 8.93 (1H, d, J = 8.0 Hz,
NH), 8.09–7.83 (5H, m, ArH), 7.58–7.55 (2H, m, ArH), 7.44 (1H, t,
J = 7.2 Hz, ArH), 7.33–7.25 (3H, m, ArH), 6.67 (1H, dd, J1 = 17.0 Hz,
J2 = 10.0 Hz,:CH), 6.21 (1H, dd, J1 = 17.0 Hz, J2 = 1.2 Hz,:CH2),
5.68 (1H, dd, J1 = 10.4 Hz, J2 = 1.2 Hz,:CH2). 13C NMR (100 MHz,
DMSO-d6): 164.9, 153.5, 147.7, 145.0, 132.9, 132.2, 131.4, 130.0,
129.7, 128.7, 128.4, 126.9, 126.3, 122.7 (CH × 2), 121.4, 120.5,
118.5, 117.5, 47.8. IR nmax (KBr): 3381, 3161, 1656, 1619, 1521,
1347, 1274, 1221, 981, 808 cm-1. MS (ESI) m/z 347 ([M-1]+, 45),
143 (5). Found: C, 68.88; H, 4.73; N, 7.98. Calc. for C20H16N2O4: C,
68.96; H, 4.63; N, 8.04%.
N-(furan-2-yl(2-hydroxynaphthalen-1-yl)methyl)benzamide (3v):
White solid m.p. 222–223°C in 80% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.27 (1H, s, OH), 9.10 (1H, d, J = 8.0 Hz, NH), 8.18
(1H, d, J = 8.4 Hz, ArH), 7.86–7.77 (4H, m, ArH), 7.55–7.44 (5H, m,
ArH), 7.30 (2H, t, J = 7.6 Hz, ArH), 7.22 (1H, d, J = 8.8 Hz, ArH),
6.37–6.35 (1H, m, ArH), 6.12 (1H, d, J = 3.2 Hz, ArH). 13C NMR
(100 MHz, DMSO-d6): 165.7, 154.1, 153.4, 142.1, 134.2, 132.3,
131.5, 129.5 (CH × 2), 128.6 (CH × 2), 128.4, 127.3, 126.5, 122.9,
122.6 (CH × 2), 118.5, 116.4, 110.5, 106.8, 44.6. IR nmax (KBr):
3410, 3147, 1632, 1401, 1345, 819, 746, 598 cm-1. MS (ESI) m/z 343
(M+, 15), 222 (100), 181 (60), 105 (55). Found: C, 76.86; H, 5.05; N,
4.01. Calc. for C22H17NO3: C, 76.95; H, 4.99; N, 4.08%.
N-((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)thiophene-
2-carboxamide (3n): White solid m.p. 130–131°C in 93% yield.
1H NMR (400 MHz, DMSO-d6): δ 10.27 (1H, s, OH), 8.96 (1H, d,
J = 8.0 Hz, NH), 8.01 (1H, d, J = 8.4 Hz, ArH), 7.91–7.78 (4H, m,
ArH), 7.44 (1H, t, J = 7.6 Hz, ArH), 7.36–7.22 (7H, m, ArH), 7.15
(1H, t, J = 4.4 Hz, ArH). 13C NMR (100 MHz, DMSO-d6): 160.8,
153.4, 140.9, 139.2 (CH × 2), 132.3, 131.2, 131.2, 129.7, 128.8, 128.7
(CH × 2), 128.4, 128.1, 128.0, 126.8, 122.8, 122.7 (CH × 2), 118.6,
117.7, 48.8. IR nmax (KBr): 3417, 1627, 1536, 1503, 1356, 1276,
815, 719 cm-1. MS (ESI) m/z 392 ([M-1]+, 25), 149 (100). Found: C,
66.96; H, 4.15; N, 3.53; S, 8.20. Calc. for C22H16ClNO2S: C, 67.08;
H, 4.09; N, 3.56; S, 8.14%.
N-((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)thiophene-
2-carboxamide (3o): Yellow solid m.p. 196–197°C in 96% yield.
1H NMR (400 MHz, DMSO-d6): δ 10.37 (1H, s, OH), 9.12 (1H, d,
J = 8.4 Hz, NH), 8.12–7.97 (4H, m, ArH), 7.88–7.80 (3H, m, ArH),
7.71 (1H, d, J = 8.0 Hz, ArH), 7.60 (1H, t, J = 8.0 Hz, ArH), 7.48
(1H, t, J = 8.0 Hz, ArH), 7.37–7.26 (3H, m, ArH), 7.19–7.17 (1H, m,
ArH). 13C NMR (100 MHz, DMSO-d6): 161.0, 153.5, 147.8, 144.4,
138.9 (CH × 2), 133.3, 131.4, 130.0, 129.7, 129.0, 128.7, 128.4,
128.0, 126.9, 122.7, 122.6, 121.6, 120.9, 118.6, 117.0, 48.9. IR nmax
(KBr): 3384, 3239, 1626, 1530, 1346, 814, 716 cm-1. MS (ESI) m/z
403 ([M-1]+, 100), 143 (18). Found: C, 65.14; H, 4.06; N, 6.93; S,
8.03. Calc. for C22H16N2O4S: C, 65.33; H, 3.99; N, 6.93; S, 7.93%.
N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)
acetamide (3p): Yellow solid m.p. 171–172°C in 89% yield.
1H NMR (400 MHz, DMSO-d6): δ 9.95 (1H, s, OH), 8.40 (1H, d,
J = 8.8 Hz, NH), 7.86–7.74 (3H, m, ArH), 7.36 (1H, t, J = 7.6 Hz,
ArH), 7.27–7.19 (2H, m, ArH), 7.08–7.04 (3H, m, ArH), 6.82–6.79
(2H, m, ArH), 3.68 (3H, s, OCH3), 1.96 (3H, s, CH3). 13C NMR
(100 MHz, DMSO-d6): 169.1, 157.7, 153.0, 134.4, 132.3, 129.1
(CH × 2), 128.5 (CH × 2), 127.2 (CH × 2), 126.2, 122.3, 119.0,
118.5, 113.4 (CH × 2), 55.0, 47.4, 22.7. IR nmax (KBr): 3396, 3056,
1628, 1513, 1438, 1255, 1177, 813, 745 cm-1. MS (ESI) m/z 320
([M-1]+, 100), 143 (8). Found: C, 74.66; H, 6.12; N, 4.30. Calc. for
C20H19NO3: C, 74.75; H, 5.96; N, 4.36%.
N-(1-(2-hydroxynaphthalen-1-yl)propyl)benzamide (3w): White
1
solid m.p. 244–245°C in 91% yield. H NMR (400 MHz, DMSO-
d6): δ 10.10 (1H, s, OH), 8.62 (1H, d, J = 8.0 Hz, NH), 8.23 (1H, d,
J = 8.8 Hz, ArH), 7.82–7.70 (4H, m, ArH), 7.54–7.44 (4H, m, ArH),
7.30 (1H, t, J = 7.2 Hz, ArH), 7.20 (1H, d, J = 8.8 Hz, ArH), 5.92
(1H, q, J = 7.6 Hz, ArH), 2.18–1.95 (2H, m, CH2), 0.93 (3H, t, CH3).
13C NMR (100 MHz, DMSO-d6): 165.4, 152.9, 134.7, 132.2, 131.0,
128.4 (CH × 2), 128.3, 128.2 (CH × 2), 126.9, 126.2, 122.5 (CH × 2),
122.3, 119.5, 118.6, 48.5, 26.9, 11.3. IR nmax (KBr): 3406, 3180,
1635, 1533, 1344, 817, 708 cm-1. MS (ESI) m/z 305 (M+, 25), 276
(86), 169 (100), 105 (90). Found: C, 78.58; H, 6.35; N, 4.51. Calc. for
C20H19NO2: C, 78.66; H, 6.27; N, 4.59%.
N,N'-(1,5-bis(2-hydroxynaphthalen-1-yl)pentane-1,5-diyl)
dibenzamide (4a): White solid m.p. 251–252°C in 4% yield. 1H NMR
(400 MHz, DMSO-d6): δ 10.15 (2H, s, OH), 8.52 (2H, s), 8.18 (2H,
s), 7.80–7.68 (8H, m, ArH), 7.53–7.41 (8H, m, ArH), 7.29 (2H, t,
J = 7.6 Hz,ArH), 7.18 (2H, d, J = 8.8 Hz,ArH), 5.99 (2H, q, J = 8.0 Hz),
2.27–2.25 (2H, m, CH2), 2.03–1.96 (2H, m, CH2), 1.64 (1H, s, CH2),
1.43 (1H, s, CH2). 13C NMR (100 MHz, DMSO-d6): 165.5 (CH × 2),
152.9 (CH × 2), 134.8 (CH × 2), 132.1 (CH × 2), 131.1 (CH × 2),
128.4 (CH × 6), 126.9 (CH × 6), 126.4 (CH × 4), 122.4 (CH × 4),
119.9 (CH × 2), 118.7 (CH × 2), 46.8 (CH × 2), 33.4 (CH × 2), 23.6.
IR nmax (KBr): 3414, 3279, 1647, 1509, 1400, 1140, 694, 617 cm-1.
MS (ESI) m/z 595 ([M + 1]+, 100). Found: C, 78.65; H, 5.91; N, 4.68.
Calc. for C39H34N2O4: C, 78.77; H, 5.76; N, 4.71%.
N-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)acetamide
(3q):
White solid m.p. 230-–231°C in 90% yield. 1H NMR (400 MHz,
DMSO-d6): δ 9.98 (1H, s, OH), 8.44 (1H, d, J = 8.4 Hz, NH), 7.84–
7.75 (3H, m, ArH), 7.36 (1H, t, J = 7.6 Hz, ArH), 7.27–7.20 (4H, m,
ArH), 7.17–7.12 (4H, m, ArH), 1.98 (3H, s, CH3). 13C NMR (100
MHz, DMSO-d6): 169.2, 153.1, 142.6, 132.3, 129.2, 128.5 (CH × 2),
128.4, 128.0 (CH × 2), 126.3, 126.0, 123.3, 122.4 (CH × 2), 118.9,
118.5, 47.8, 22.6. IR nmax (KBr): 3401, 3252, 1641, 1515, 1338,
1278, 808, 743, 697 cm-1. MS (ESI) m/z 290 ([M-1]+, 60), 149 (15).
Found: C, 78.21; H, 6.01; N, 4.78. Calc. for C19H17NO2: C, 78.33; H,
5.88; N, 4.81%.
N-((2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)acetamide
(3r): Yellow solid m.p. 255–256°C in 93% yield. 1H NMR
(400 MHz, DMSO-d6): δ 10.13 (1H, s, OH), 8.63 (1H, d, J = 8.0 Hz,
NH), 8.06–8.01 (2H, m, ArH), 7.88–7.80 (3H, m, ArH), 7.59–7.53
(2H, m, ArH), 7.42 (1H, t, J = 7.6 Hz, ArH), 7.30 (1H, t, J = 7.6 Hz,
ArH), 7.23–7.17 (2H, m, ArH), 2.02 (3H, s, CH3). 13C NMR (100
MHz, DMSO-d6): 169.7, 153.3, 147.7, 145.4, 132.8, 132.1, 129.9,
129.5, 128.7, 128.4, 126.8, 122.8, 122.6, 121.2, 120.4, 118.4, 117.8,
47.6, 22.5. IR nmax (KBr): 3375, 3222, 1649, 1525, 1350, 806, 734
cm-1. MS (ESI) m/z 335 ([M-1]+, 70), 143 (5). Found: C, 67.76; H,
4.87; N, 8.30. Calc. for C19H16N2O4: C, 67.85; H, 4.79; N, 8.33%.
N-((2-hydroxynaphthalen-1-yl)(4-methoxyphenyl)methyl)acrylamide
(3s): White solid m.p. 222–223°C in 90% yield. 1H NMR (400 MHz,
DMSO-d6):δ10.00(1H,s,OH),8.68(1H,d,J=8.4Hz,NH),7.88–7.75
(3H, m, ArH), 7.39–7.06 (6H, m, ArH), 6.84–6.80 (2H, m, ArH), 6.57
(1H, dd, J1 = 16.8 Hz, J2 = 10.4 Hz,:CH), 6.11 (1H, dd, J1 = 17.0 Hz,
J2 = 2.0 Hz,:CH2), 5.60 (1H, dd, J1 = 10.2 Hz, J2 = 2.4 Hz,:CH2),
3.68 (3H, s, OCH3). 13C NMR (100 MHz, DMSO-d6): 164.4, 157.8,
153.2, 134.0, 132.3, 131.9, 129.2 (CH × 2), 128.6, 128.5, 127.4,
126.3, 125.6, 123.3, 122.4, 118.6, 118.5, 113.5 (CH × 2), 55.0, 47.7.
IR nmax (KBr): 3398, 3071, 1657, 1512, 1439, 1337, 1247, 1174,
818, 654 cm-1. MS (ESI) m/z 332 ([M-1]+, 15), 293 (50), 195 (100),
143 (3). Found: C, 75.58; H, 5.83; N, 4.15. Calc. for C21H19NO3: C,
75.66; H, 5.74; N, 4.20%.
1,3-bis((2-hydroxynaphthalen-1-yl)(phenyl)methyl)urea
(5a):
White solid m.p. 168–169°C in 58% yield. 1H NMR (400 MHz,
DMSO-d6): δ 9.85 (2H, s, OH), 7.77–7.69 (7H, m, ArH), 7.44–7.05
(19H,m,ArH).13CNMR(100MHz,DMSO-d6):158.0,152.8(CH×2),
144.6 (CH × 2), 132.2 (CH × 2), 128.9 (CH × 4), 128.5(CH × 6),
127.9 (CH × 4), 126.2 (CH × 4), 125.8 (CH × 2), 122.2 (CH × 2),
120.2 (CH × 2), 118.4 (CH × 2), 48.0 (CH × 2). IR nmax (KBr): 3415,
3395, 1631, 1531, 1273, 1068, 814, 745, 698 cm-1. MS (ESI) m/z
525 ([M + 1]+, 100). Found: C, 80.01; H, 5.51; N, 5.28. Calc. for
C35H28N2O3: C, 80.13; H, 5.38; N, 5.34%.
N-((1-hydroxynaphthalen-2-yl)(3-nitrophenyl)methyl)benzamide
1
(6a): Sorrel solid m.p. 83–84°C in 60% yield. H NMR (400 MHz,
DMSO-d6): δ 9.79 (1H, s, OH), 9.38 (1H, d, J = 9.2 Hz, NH), 8.27–
8.25 (1H, m, ArH), 8.17–8.12 (2H, m, ArH), 7.96–7.81 (4H, m, ArH),
7.67–7.47 (8H, m, ArH), 7.15 (1H, d, J = 8.4 Hz, CH). 13C NMR
(100 MHz, DMSO-d6): 166.4, 149.5, 147.8, 144.9, 134.3 (CH × 2),
133.7, 131.6, 129.9, 128.4 (CH × 2), 127.7, 126.2 (CH × 2), 125.8
(CH × 2), 125.3, 122.6 (CH × 2), 122.2, 121.9, 121.7, 119.9, 50.6. IR
N-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)acrylamide
(3t):
White solid m.p. 255–256°C in 90% yield. 1H NMR (400 MHz,
DMSO-d6): δ 10.02 (1H, s, OH), 8.71 (1H, d, J = 8.4 Hz, NH), 7.87–
7.76 (3H, m, ArH), 7.37 (1H, t, J = 7.6 Hz, ArH), 7.28–7.15 (8H, m,
ArH), 6.60 (1H, dd, J1 = 17.2 Hz, J2 = 10.0 Hz,:CH), 6.13 (1H, dd,
n
max (KBr): 3421, 3126, 1664, 1530, 1400, 1349 cm-1. MS (ESI) m/z
398 (M+, 5), 230 (85), 105 (100). Found: C, 72.23; H, 4.62; N, 6.99.
Calc. for C24H18N2O4: C, 72.35; H, 4.55; N, 7.03%.
PAPER: 08/5086

128 JOURNAL OF CHEMICAL RESEARCH 2008
20 C. Cimarelli, A. Mazzanti, G. Palmieri and E. Volpini, J. Org. Chem.,
2001, 66, 4759.
21 J.-X. Ji, L.-Q. Qiu, C.W. Yip and A.S.C. Chan, J. Org. Chem., 2003, 68,
1589.
22 N.K. Paul, L. Dietrich and A. Jha, Synth. Commun., 2007, 37, 877.
23 A. Jha, N.K. Paul, S. Trikha and T.S. Cameron, Can. J. Chem., 2006,
84, 843.
We thank the National Natural Science Foundation of China
[20676123] for financial support.
Received 3 February 2008; accepted 24 February 2008
Paper 08/5086
doi: 10.3184/030823408X298508
24 M. Periasamy, M.N. Reddy and S. Anwar, Tetrahedron: Asymmetry, 2004,
15, 1809.
25 M.R. Saidi, N. Azizi and M.R. Naimi-Jamal, Tetrahedron Lett., 2001, 42,
8111.
References
1
2
M. Schapira, R. Abagyan and M. Totrov, J. Med. Chem., 2003, 46, 3045.
I.T. Harrison, B. Lewis, P. Nelson, W. Rooks, A. Roszkowski,
A. Tomolonis and J.H. Fried, J. Med. Chem., 1970, 13, 203.
A.C. Goudie, L.M. Gaster, A.W. Lake, C.J. Rose, P.C. Freeman,
B.O. Hughes and D. Miller, J. Med. Chem., 1978, 21, 1260.
G. Petranyi, N.S. Ryder and A. Stuetz, Science, 1984, 224, 1239.
A.A. Kyle and M.V. Dahl, Am. J. Clin. Dermatol., 2004, 5, 443.
P. Hurwitz and J.M. Thompson, Arch. Ophthal., 1950, 43, 712.
F.E. Gardner, P.C. Marth and L.P. Batjer, Science, 1939, 90, 208.
T.E. Archer and J.D. Stokes, J. Agric. Food. Chem., 1980, 28, 877.
B. Duperray, M. Chastrette, M.C. Makabeh and H. Pacheco, Eur. J. Med.
Chem., 1976, 11, 433.
26 M.R. Saidi and N. Azizi, Tetrahedron: Asymmetry, 2003, 14, 389.
27 M. Dabiri, A.S. Delbari and A. Bazgir, Heterocycles, 2007, 71, 543.
28 M.M. Khodaei, A.R. Khosropour and H. Moghanian, Synlett, 2006, 916.
29 S.B. Patil, P.R. Singh, M.P. Surpur and S.D. Samant, Synth. Commun.,
2007, 37, 1659.
30 A. Domling and I. Ugi, Angew. Chem. Int. Ed., 2000, 39, 3168.
31 I. Ugi, A. Domling and W. Horl, Endeavour, 1994, 18, 115.
32 S. Heck and A. Domling, Synlett, 2000, 424.
33 L.A. Thompson and J.A. Ellman, Chem. Rev., 1996, 96, 555.
34 S. Kobayashi, M. Sugiura, H. Kitagawa and W.W.-L. Lam, Chem. Rev.,
2002, 102, 2227.
35 W.-K. Su and C. Jin, Org. Lett., 2007, 9, 993.
36 W.-K. Su, J.-X. Chen, H.-Y. Wu and C. Jin, J. Org. Chem., 2007, 72,
4524.
37 C.-M. Yu, X.-P. Dai and W.-K. Su, Synlett, 2007, 646.
38 W.-K. Su, J.-J. Li, Z.-G. Zheng and Y.-C. Shen, Tetrahedron Lett., 2005,
46, 6037.
39 J.H. Forsberg, V.T. Spaziano, T.M. Balasubramanian, G.K. Liu,
S.A. Kinsley, C.A. Duckworth, J.J. Poteruca, P.S. Brown and J.L. Miller,
J. Org. Chem., 1987, 52, 1017.
40 C.O. Kappe, J. Org. Chem., 1997, 62, 7201.
41 Y. Ma, C.-T. Qian, L.-M. Wang and M. Yang, J. Org. Chem., 2000, 65,
3864.
42 S.-L. Huang, Y.-J. Pan, Y.-L. Zhu and A.-X. Wu, Org. Lett., 2005, 7,
3797.
43 P. Cristau, J.P. Vors and J.-P. Zhu, Tetrahedron Lett., 2003, 44, 5575.
3
4
5
6
7
8
9
10 A.F. Hardman, US Pat., 2 375 168, 1945.
11 P. Kocovsky, S. Vyskocil and M. Smrcina, Chem. Rev., 2003, 103, 3213.
12 S. Vyskocil, S. Jaracz, M. Smrcina, M. Sticha, V. Hanus, M. Polasek and
P. Kocovsky, J. Org. Chem., 1998, 63, 7727.
13 M. Smrcina, M. Lorenc, V. Hanus, P. Sedmera and P. Kocovsky, J. Org.
Chem., 1992, 57, 1917.
14 Y. Yuan, X. Li, J. Sun and K.-L. Ding. J. Am. Chem. Soc., 2002, 124,
14866.
15 G. Bernardinelli, D. Fernandez, R. Gosmini, P. Meier, A. Ripa,
P. Schupfer, B. Treptow and E.P. Kundig, Chirality, 2000, 12, 529.
16 C. Cardellicchio, G. Ciccarella, F. Naso, E. Schingaro and F. Scordari,
Tetrahedron: Asymmetry, 1998, 9, 3667.
17 G. Palmieri, Tetrahedron: Asymmetry, 2000, 11, 3361.
18 D.-X. Liu, L.-C. Zhang, Q. Wang, C.-S. Da, Z.-Q. Xin, R. Wang,
M.C.K. Choi and A.S.C. Chan, Org. Lett., 2001, 3, 2733.
19 C. Cimarelli, G. Palmieri and E. Volpini, Tetrahedron: Asymmetry, 2002,
13, 2417.
PAPER: 08/5086