Facile and green method for the synthesis of-aminoketone derivatives in aqueous media

Article abstract of DOI:10.1080/00397910903029859

Three-component reaction of aromatic aldehyde, 2-naphthalenamine, and 1,2-diphenylethanone in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90C gave 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan- 1-one derivatives. The enol fo

Full text of DOI:10.1080/00397910903029859

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Facile and Green Method for the
Synthesis of β-Aminoketone Derivatives
in Aqueous Media
Xiang-Shan Wang a b , Jie Zhou a , Ke Yang a & Qing Li a
a School of Chemistry and Chemical Engineering, Xuzhou Normal
University, Xuzhou, Jiangsu, China
b Key Laboratory of Biotechnology on Medical Plant, Xuzhou,
Jiangsu, China
Published online: 04 Mar 2010.
To cite this article: Xiang-Shan Wang , Jie Zhou , Ke Yang & Qing Li (2010) Facile and Green Method
for the Synthesis of β-Aminoketone Derivatives in Aqueous Media, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry, 40:7, 964-972, DOI:
10.1080/00397910903029859
To link to this article: http://dx.doi.org/10.1080/00397910903029859
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Synthetic Communications1, 40: 964–972, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903029859
FACILE AND GREEN METHOD FOR THE SYNTHESIS OF
b-AMINOKETONE DERIVATIVES IN AQUEOUS MEDIA
Xiang-Shan Wang,1,2 Jie Zhou,1 Ke Yang,1 and Qing Li1
1School of Chemistry and Chemical Engineering, Xuzhou Normal University,
Xuzhou, Jiangsu, China
2Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, China
Three-component reaction of aromatic aldehyde, 2-naphthalenamine, and 1,2-diphenyletha-
none in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90 ꢀC
gave 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives. The enol form
of 1,2-diphenylethanone was tentatively proposed to participate in the formation of the pro-
ducts. Compared with previous methods, this three-component reaction has the advantages
of green solvent, good yields, and operational simplicity.
Keywords: Aqueous media; 1,2-diphenylethanone; 2-naphthalenamine; TEBAC
INTRODUCTION
Compounds containing 1,3-amino-oxygenated functional moieties are
ubiquitous to a variety of biologically important natural products and potent drugs,
including a number of nucleoside antibiotics and HIV protease inhibitors.[1] Of
particular interest would be a facile method for the construction of 1,3-amido
alcohols, as these molecules are versatile precursors for 1,3-amino alcohols and
ligands for asymmetric catalysts.[2] It is noteworthy that aminotetraline derivatives
manifest a number of important and therapeutically useful biological activities such
as antidepressant, immunomodulatory, and antitumor activities.[3]
Despite this broad range of applications, only a few members of this family of
compounds have been reported,[4] of which the main class was 1-amidoalkyl-2-
naphthols and their derivatives. They are always catalyzed by Lewis or Brønsted
acid catalysts such as Montmorillonite K10 clay,[5] Ce(SO4)2,[6] iodine,[7]
K5CoW12O40 ꢁ 3H2O,[8] p-TSA,[9] sulfamic acid,[10] cation-exchanged resins,[11] and
silica-sulfuric acid.[12] It should be noted that they were all performed in organic
solvent; furthermore, only a few studies were concerned about 1,3-aminoketone,[13]
so the development of a green method for 1,3-amino-oxygenated functional moieties
was therefore of considerable synthetic importance.
Received December 25, 2008.
Address correspondence to Xiang-Shan Wang, School of Chemistry and Chemical Engineering,
Xuzhou Normal University, Xuzhou, Jiangsu 221116, China. E-mail: xswang1974@yahoo.com
964

SYNTHESIS OF b-AMINOKETONE DERIVATIVES
965
Development of organic reactions in water without use of harmful organic
solvents is one of the current focuses, especially in the environmentally conscious
focus today. Water has recently attracted considerable interest as a solvent for a
large number of organic transformations[14] because it is abundant, nontoxic, and
environmentally friendly compared to organic solvents. As part of our ongoing
program to synthesize these active compounds in an environmentally friendly
media,[15] herein we report a green synthesis of a series of 1,3-aminoketone deriva-
tives in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC)
by three-component reaction of aromatic aldehyde, 2-naphthalenamine, and
1,2-diphenylethanone.
RESULTS AND DISCUSSION
The treatment of aromatic aldehyde 1, 2-naphthalenamine 2, and 1,2-dipheny-
lethanone 3 in water using 10 mol% TEBAC as phase-transfer catalysis at 90 ꢀC
afforded 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives 4
in good to high yields (Scheme 1).
Subsequently, the reaction of 3-nitrobenzaldehyde, 1,2-diphenylethanone, and
2-naphthalenamine was used as a model reaction to optimize the conditions. The
reaction was first carried out in water in the absence of TEBAC. At room tempera-
ture, no reaction took place (Table 1, entry 1), and only a trace product of 3a was
observed by thin-layer chromatography (TLC) when the reaction temperature was
raised to 90 ꢀC (Table 1, entry 2). Similar reactions were then attempted in the
presence of TEBAC with 1, 5, 10, and 20 mol% (Table 1, entries 5–8); just 10 mol%
TEBAC at 90 ꢀC in water gave the best yield. Greater amounts of the catalyst did
not improve the yield. To find the optimum reaction temperature, the reaction was
carried out in the presence of TEBAC with 10 mol% at room temperature, 50 ꢀC,
and 90 ꢀC, resulting in the isolation of 4a in trace, 62%, and 86% yield (Table 1, entries
3–5), respectively. Thus, 10 mol% TEBAC and a reaction temperature of 90 ꢀC were
chosen. In addition, CH3(CH2)15NMe3Br and CH3(CH2)11SO3Na (Table 1, entries 9
and 10) were also tested as the catalyst. In these cases, product 4a was formed in
slightly lower yields. The TEBAC could be reused for the synthesis of 4a without
significant loss of activity, and even in the fourth round, 4a could be obtained in good
yield (78%).
To extend the reaction (Scheme 1) to a library system, various kinds of aromatic
aldehydes 1 were reacted with 1,2-diphenylethanone and 2-naphthalenamine, giving
the corresponding 3-aryl-3-(naphthalen-2-ylamino) 1,2-diphenylpropan-1-one deri-
vatives 4 successfully (Table 2). All of 1 gave expected products in good yields, either
Scheme 1. Reaction of aromatic aldehyde and 1,2-diphenylethanone and 2-naphthalenamine.

966
X.-S. WANG ET AL.
Table 1. Synthesis of 4a in water under different reaction conditionsa
Entry
Temp. (ꢀC)
Cat. (mol%)
Catalyst
Yieldb (%)
1
2
rt
0
0
—
—
0
trace
trace
62
90
rt
3
10
10
10
20
5
TEBAC
TEBAC
4
50
90
90
90
90
90
90
5
TEBAC
TEBAC
86
85
6
7
TEBAC
TEBAC
78
76
8
1
9
10
10
10
CH3(CH2)15NMe3Br
CH3(CH2)11SO3Na
82
83
aReagents and conditions: 1 (0.302 g, 2 mmol), 2-naphthalenamine 2 (0.286 g, 2 mmol),
1,2-diphenylethanone 3 (0.392 g, 2 mmol), and TEBAC (0.091 g, 0.2 mmol), solvent (10 mL).
bIsolated yields.
bearing electron-withdrawing groups (such as halide, nitro) or electron-donating
groups (such as alkyl group, or alkoxyl group) under the same reaction conditions
(Table 2). The other aromatic amines, such as aniline or p-toluidine, were also chosen
as reactants to react with 1 and 1,2-diphenylethanone. However, they all gave a
complicated system in this TEBAC-H2O reaction condition.
Although the detailed mechanism of the reaction has not been clarified, the
formation of 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives
4 could be explained by a possible mechanism as presented in Scheme 2. The conden-
sation of aromatic aldehydes and 2-naphthalenamine may occur to generate Schiff
=
base first, then the enol form of 1,2-diphenylethanone attacks the C N double bond
to give the final product. In this process, the action of TEBAC is as phase-transfer
catalysis.
Table 2. Reactions of aromatic aldehyde and 1,2-diphenylethanone and 2-naphthalenamine in watera
Entry
Ar
Products
Time (h)
Yields (%)b
1
2
3-NO2C6H4
4-NO2C6H4
3-ClC6H4
4a
4b
4c
4d
4e
4f
10
10
12
16
15
18
16
15
16
14
16
15
86
87
83
85
88
79
90
89
78
89
92
87
3
4
4-ClC6H4
3-BrC6H4
4-BrC6H4
5
6
7
4-CH3C6H4
4-CH3OC6H4
3,4-Cl2C6H3
4-FC6H4
4g
4h
4i
8
9
10
11
12
4j
3,4-OCH2OC6H3
3-FC6H4
4k
4l
aReagents and conditions: 1 (2 mmol), 2-naphthalenamine 2 (0.286 g, 2 mmol), 1,2-diphenylethanone 3
(0.392 g, 2 mmol), TEBAC (0.091 g, 0.2 mmol), and solvent (10 mL).
bIsolated yields.

SYNTHESIS OF b-AMINOKETONE DERIVATIVES
967
Scheme 2. Possible mechanism of the reaction.
CONCLUSION
In conclusion, we found a facile and green method for the synthesis of 3-aryl-3-
(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives by three-component
reaction of aromatic aldehyde, 2-naphthalenamine, and 1,2-diphenylethanone in
aqueous media catalyzed by TEBAC at 90 ꢀC. Compared with previous methods,
this three-component reaction has the advantages of green solvent, good to high
yields, and operational simplicity.
EXPERIMENTAL
Melting points were determined in open capillaries and are uncorrected. Infra-
red (IR) spectra were recorded on a Tensor 27 spectrometer in KBr pellets. 1H NMR
spectra were obtained from solution in dimethylsulfoxide (DMSO-d6) or CDCl3 with
Me4Si as internal standard using a Bruker 400 spectrometer. High-resolution mass
spectrometric (HRMS) analyses were carried out using a Bruker Micro-TOF-Q-
MS analyzer.
General Procedure for the Syntheses of 3-Aryl-3-(naphthalen-
2-ylamino)-1,2-diphenylpropan-1-one Derivatives
A 50-mL flask was charged with aromatic aldehyde (2.0 mmol), 1,2-diphenyl-
ethanone (2.0 mmol, 0.392 g), 2-naphthalenamine (2.0 mmol, 0.286 g), TEBAC
(0.2 mmol, 0.091 g), and water (10 mL). The reaction mixture was stirred at 90 ꢀC
for 10–18 h; the solid was isolated by filtration. The filtrate, together with TEBAC,
could be used directly for the same reaction. The crude products were washed with
water, purified by recrystallization from dimethylformamide (DMF) and water, and
dried at 80 ꢀC for several hours in a vacuum to give 4.
Selected Data
1,2-Diphenyl-3-(naphthalen-2-ylamino)-3-(3-nitrophenyl)propan-1-one
(4a). Mp 216–217 ꢀC. IR (KBr): 3404, 3061, 1604, 1632, 1596, 1532, 1493, 1476,
.
1401, 1354, 1286, 1268, 1191, 822, 806, 754, 739, 698 cmꢂ1 1H NMR (CDCl3,
400 MHz): 4.28 (s, 1H, NH), 5.00 (d, J ¼ 9.6 Hz, 1H, CH), 5.45 (dd, J ¼ 9.6 Hz,
J0 ¼ 3.2 Hz, 1H, ArH), 6.55 (d, J ¼ 2.0 Hz, 1H, ArH), 6.69 (dd, J ¼ 8.8 Hz,
J0 ¼ 2.0 Hz, 1H, ArH), 7.13–7.77 (m, 1H, ArH), 7.27–7.49 (m, 11H, ArH), 7.51

968
X.-S. WANG ET AL.
(d, J ¼ 8.8 Hz, 1H, ArH), 7.58 (d, J ¼ 8.4 Hz, 1H, ArH), 7.78 (d, J ¼ 7.6 Hz, 1H,
ArH), 7.92 (d, J ¼ 7.6 Hz, 1H, ArH), 8.02 (dd, J ¼ 8.0 Hz, J0 ¼ 1.6 Hz, 1H, ArH),
8.45 (s, 1H, ArH). HRMS (ESI, m=z): calcd. for C31H25N2O3 (M þ Hþ) 473.1865;
found 473.1861.
1,2-Diphenyl-3-(naphthalen-2-ylamino)-3-(3-nitrophenyl)propan-1-one
(4b). Mp 175–176 ꢀC. IR (KBr): 3414, 3057, 1680, 1632, 1629, 1599, 1580, 1521,
1448, 1397, 1346, 1291, 1262, 1228, 1202, 1191, 1145, 1107, 1091, 981, 851, 831,
748, 700 cmꢂ1
.
1H NMR (DMSO-d6, 400 MHz): 5.35 (d, J ¼ 10.8 Hz, 1H, CH),
5.61–5.66 (m, 1H, CH), 6.88 (b, 2H, ArH þ NH), 6.98 (d, J ¼ 8.8 Hz, 1H, ArH),
7.07–7.11 (m, 2H, ArH), 7.14–7.17 (m, 2H, ArH), 7.25–7.29 (m, 3H, ArH),
7.50–7.70 (m, 8H, ArH), 7.97 (d, J ¼ 8.0 Hz, 2H, ArH), 8.13 (d, J ¼ 8.0 Hz, 2H,
ArH). HRMS (ESI, m=z): calcd. for C31H24N2O3Na (M þ Naþ) 495.1685; found
495.1681.
3-(3-Chlorophenyl)-1,2-diphenyl-3-(naphthalen-2-ylamino)propan-1-one
(4c). Mp 222–223 ꢀC. IR (KBr): 3410, 3053, 3023, 1669, 1633, 1595, 1578, 1531, 1492,
1
1474, 1488, 1401, 1354, 1285, 1268, 1206, 1191, 823, 805, 769, 740, 703 cmꢂ1. H
NMR (CDCl3, 400 MHz): 4.16 (s, 1H, NH), 4.96 (d, J ¼ 9.2 Hz, 1H, CH), 5.32 (d,
J ¼ 9.2 Hz, 1H, CH), 6.95 (d, J ¼ 2.0 Hz, 1H, ArH), 6.67 (dd, J ¼ 8.8 Hz, J0 ¼ 2.0 Hz,
1H, ArH), 7.11–7.20 (m, 3H, ArH), 7.28–7.36 (m, 5H, ArH), 7.42–7.59 (m, 9H, ArH),
7.78 (d, J ¼ 7.6 Hz, 2H, ArH). HRMS (ESI, m=z): calcd. for C31H25ClNO (M þ Hþ)
462.1625; found 462.1606.
3-(4-Chlorophenyl)-1,2-diphenyl-3-(naphthalen-2-ylamino)propan-1-one
(4d). Mp 223–224 ꢀC. IR (KBr): 3400, 3055, 3024, 1667, 1631, 1597, 1580, 1529,
1489, 1448, 1401, 1354, 1285, 1213, 1190, 1014, 852, 829, 815, 752, 742, 703 cmꢂ1
.
1H NMR (DMSO-d6, 400 MHz): 5.35 (t, J ¼ 10.0 Hz, 1H, CH), 5.48 (d, J ¼ 10.8 Hz,
1H, CH), 6.33 (d, J ¼ 10.0 Hz, 1H, NH), 6.78 (s, 1H, ArH), 6.84 (dd, J ¼ 9.2 Hz,
J0 ¼ 1.6 Hz, 1H, ArH), 7.03–7.07 (m, 1H, ArH), 7.17–7.33 (m, 6H, ArH),
7.43–7.58 (m, 6H, ArH), 7.64 (d, J ¼ 8.8 Hz, 2H, ArH), 7.69 (d, J ¼ 8.4 Hz, 2H,
ArH), 7.85 (d, J ¼ 7.6 Hz, 2H, ArH). HRMS (ESI, m=z): calcd. for C31H25ClNO
(M þ Hþ) 462.1625; found 462.1604.
3-(3-Bromophenyl)-1,2-diphenyl-3-(naphthalen-2-ylamino)propan-1-one
(4e). Mp 203–204 ꢀC. IR (KBr): 3410, 3052, 3022, 1669, 1632, 1595, 1531, 1492,
1471, 1447, 1401, 1353, 1285, 1267, 1229, 1205, 1189, 1071, 995, 823, 805, 740,
.
701 cmꢂ1 1H NMR (DMSO-d6, 400 MHz): 5.34–5.38 (m, 1H, CH), 5.5 (d,
J ¼ 11.2 Hz, 1H, CH), 6.30 (d, J ¼ 9.6 Hz, 1H, NH), 6.79–7.05 (m, 2H, ArH),
7.07–7.18 (m, 1H, ArH), 7.19–7.33 (m, 6H, ArH), 7.46–7.70 (m, 10H, ArH), 7.86
(d, J ¼ 7.6 Hz, 2H, ArH). HRMS (ESI, m=z): calcd. for C31H25BrNO (M þ Hþ)
506.1120; found 506.1117.
3-(4-Bromophenyl)-1,2-diphenyl-3-(naphthalen-2-ylamino)propan-1-one
(4f). Mp 223–224 ꢀC. IR (KBr): 3400, 3055, 3024, 1667, 1631, 1597, 1580, 1529,
1
1486, 1448, 1402, 1353, 1285, 1214, 1190, 1010, 829, 814, 751, 742, 698 cmꢂ1. H
NMR (CDCl3, 400 MHz): 4.16 (s, 1H, NH), 4.95 (d, J ¼ 9.6 Hz, 1H, CH), 5.32
(d, J ¼ 9.2 Hz, 1H, CH), 6.56 (d, J ¼ 2.0 Hz, 1H, ArH), 6.66 (dd, J ¼ 8.8 Hz,

SYNTHESIS OF b-AMINOKETONE DERIVATIVES
969
J0 ¼ 2.0 Hz, 1H, ArH), 7.12–7.16 (m, 1H, ArH), 7.27–7.38 (m, 7H, ArH),
7.42–7.50 (m, 8H, ArH), 7.58 (d, J ¼ 8.0 Hz, 1H, ArH), 7.76 (d, J ¼ 8.4 Hz, 2H,
ArH). HRMS (ESI, m=z): calcd. for C31H25BrNO (M þ Hþ) 506.1120; found
506.1116.
1,2-Diphenyl-3-(4-methylphenyl)-3-(naphthalen-2-ylamino)propan-1-one
(4g). Mp 201–203 ꢀC. IR (KBr): 3402, 3054, 3024, 1670, 1630, 1596, 1579, 1529,
1
1490, 1448, 1401, 1354, 1285, 1212, 1191, 851, 830, 813, 743, 697 cmꢂ1. H NMR
(DMSO-d6, 400 MHz): 2.11 (s, 3H, CH3), 5.29–5.34 (m, 1H, CH), 5.48 (d,
J ¼ 10.8 Hz, 1H, CH), 6.23 (d, J ¼ 9.6 Hz, 1H, NH), 6.77 (s, 1H, ArH), 6.84 (d,
J ¼ 8.4 Hz, 1H, ArH), 6.99–7.06 (m, 3H, ArH), 7.17–7.26 (m, 2H, ArH), 7.29–7.33
(m, 2H, ArH), 7.43–7.56 (m, 8H, ArH), 7.62 (d, J ¼ 7.6 Hz, 2H, ArH), 7.85
(d, J ¼ 7.6 Hz, 2H, ArH). HRMS (ESI, m=z): calcd. for C32H28NO (M þ Hþ)
442.2171; found 442.2171.
1,2-Diphenyl-3-(4-methoxyphenyl)-3-(naphthalen-2-ylamino)propan-1-
one (4h). Mp 181–182 ꢀC. IR (KBr): 3387, 3052, 2960, 2930, 1666, 1630, 1598,
1579, 1527, 1512, 1449, 1398, 1356, 1287, 1275, 1254, 1207, 1178, 1026, 828, 812,
744, 706, 696 cmꢂ1
.
1H NMR (DMSO-d6, 400 MHz): 3.60 (s, 3H, CH3O),
5.28–5.33 (m, 1H, CH), 5.48 (d, J ¼ 11.2 Hz, 1H, CH), 6.22 (d, J ¼ 10.0 Hz, 1H,
NH), 6.74–6.79 (m, 2H, ArH), 6.85 (d, J ¼ 7.6 Hz, 1H, ArH), 7.03–7.06 (m, 1H,
ArH), 7.17–7.33 (m, 4H, ArH), 7.43–7.63 (m, 11H, ArH), 7.85 (d, J ¼ 7.2 Hz, 2H,
ArH). HRMS (ESI, m=z): calcd. for C32H28NO2 (M þ Hþ) 458.2120; found
458.2117.
3-(3,4-Dichlorophenyl)-1,2-diphenyl-3-(naphthalen-2-ylamino)propan-1-
one (4i). Mp 214–215 ꢀC. IR (KBr): 3392, 3055, 3024, 1663, 1630, 1596, 1579, 1529,
1469, 1447, 1400, 1353, 1285, 1215, 1190, 1125, 1030, 902, 829, 815, 756, 742, 718,
.
705 cmꢂ1 1H NMR (DMSO-d6, 400 MHz): 5.37–5.42 (m, 1H, CH), 5.51 (d,
J ¼ 10.4 Hz, 1H, CH), 6.30 (d, J ¼ 10.0 Hz, 1H, NH), 6.86–6.89 (m, 2H, ArH),
7.05–7.29 (m, 1H, ArH), 7.18–7.34 (m, 4H, ArH), 7.44–7.63 (m, 9H, ArH), 7.69
(dd, J ¼ 8.4 Hz, J0 ¼ 2.0 Hz, 1H, ArH), 7.87 (d, J ¼ 7.2 Hz, 2H, ArH), 7.99 (d,
J ¼ 1.6 Hz, 1H, ArH). HRMS (ESI, m=z): calcd. for C31H23Cl2NONa (M þ Naþ)
518.1054; found 518.1050.
1,2-Diphenyl-3-(4-fluorophenyl)-3-(naphthalen-2-ylamino)propan-1-one
(4j). Mp 201–202 ꢀC. IR (KBr): 3399, 3055, 1666, 1633, 1598, 1531, 1507, 1448,
1403, 1356, 1285, 1269, 1227, 1206, 1190, 1157, 959, 851, 823, 804, 744, 703 cmꢂ1
.
1H NMR (DMSO-d6, 400 MHz): 5.35–5.40 (m, 1H, CH), 5.48–5.50 (m, 1H, CH),
6.29 (d, J ¼ 9.6 Hz, 1H, NH), 6.80 (s, 1H, ArH), 6.86 (d, J ¼ 9.2 Hz, 1H, ArH),
7.01–7.18 (m, 3H, ArH), 7.20–7.26 (m, 2H, ArH), 7.30–7.34 (m, 2H, ArH),
7.43–7.57 (m, 6H, ArH), 7.63–7.73 (m, 4H, ArH), 7.84 (d, J ¼ 7.2 Hz, 2H, ArH).
HRMS (ESI, m=z): calcd. for C31H25FNO (M þ Hþ) 446.1920; found 446.1910.
1,2-Diphenyl-3-(3,4-methylenedioxylphenyl)-3-(naphthalen-2-ylamino)
propan-1-one (4k). Mp 217–218 ꢀC. IR (KBr): 3405, 3055, 3023, 1667, 1633, 1607,
1594, 1531, 1482, 1448, 1401, 1353, 1357, 1285, 1267, 1234, 1203, 1191, 1142, 1004,
1
950, 824, 804, 740, 702 cmꢂ1. H NMR (DMSO-d6, 400 MHz): 5.27–5.32 (m, 1H,

970
X.-S. WANG ET AL.
CH), 5.45 (d, J ¼ 10.4 Hz, 1H, CH), 5.85 (d, J ¼ 3.2 Hz, 2H, OCH2O), 6.18 (d,
J ¼ 9.6 Hz, 1H, NH), 6.73 (d, J ¼ 8.0 Hz, 1H, ArH), 6.81–6.86 (m, 2H, ArH),
7.04–7.33 (m, 7H, ArH), 7.45–7.62 (m, 8H, ArH), 7.87 (d, J ¼ 7.2 Hz, 2H, ArH).
HRMS (ESI, m=z): calcd. for C32H26NO3 (M þ Hþ) 472.1909; found 472.1909.
1,2-Diphenyl-3-(3-fluorophenyl)-3-(naphthalen-2-ylamino)propan-1-one
(4l). Mp 223–224 ꢀC. IR (KBr): 3396, 3054, 1666, 1630, 1597, 1578, 1530, 1503,
1488, 1442, 1398, 1354, 1284, 1243, 1204, 1190, 1037, 929, 829, 812, 750, 743,
706 cmꢂ1 1H NMR (DMSO-d6, 400 MHz): 5.37–5.42 (m, 1H, CH), 5.50 (d,
.
J ¼ 10.4 Hz, 1H, CH), 6.30 (d, J ¼ 10.0 Hz, 1H, NH), 6.84–6.88 (m, 3H, ArH),
7.04–7.08 (m, 1H, ArH), 7.18–7.34 (m, 5H, ArH), 7.44–7.58 (m, 8H, ArH), 7.63
(d, J ¼ 8.0 Hz, 2H, ArH), 7.86 (d, J ¼ 8.0 Hz, 2H, ArH). HRMS (ESI, m=z): calcd.
for C31H25FNO (M þ Hþ) 446.1920; found 446.1914.
ACKNOWLEDGMENTS
We are grateful to the National Natural Science Foundation of China
(20802061), the Natural Science Foundation (08KJD150019), and the Qing Lan
Project (08QLT001) of Jiangsu Education Committee for financial support.
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