L-Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-8(7H)- ones at room temperature

Article abstract of DOI:10.1016/j.crci.2011.12.001

Only 10 mol% of l-Proline in ethanol proved to be a very efficient catalyst for the one-pot synthesis of a wide variety of highly substituted tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature. The key advantages of this process are high yields, cos

Full text of DOI:10.1016/j.crci.2011.12.001

C. R. Chimie 15 (2012) 448–453
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Full paper/Memoire
L-Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-
8(7H)-ones at room temperature
*
Mohammad Reza Poor Heravi , Parinaz Aghamohammadi
Payame Noor University, Department of Chemistry, 19395-4697, Tehran, Iran
A R T I C L E I N F O
A B S T R A C T
Only 10 mol% of
Article history:
L
-Proline in ethanol proved to be a very efficient catalyst for the one-pot
Received 1 November 2011
Accepted after revision 2 December 2011
Available online 4 January 2012
synthesis of a wide variety of highly substituted tetrahydrobenzo[c]acridin-8(7H)-ones at
room temperature. The key advantages of this process are high yields, cost effectiveness of
the catalyst, easy work-up and the products can be directly recrystallized from hot
ethanol.
Keywords:
ß 2011 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
L-Proline
Oregano catalyst
Dimedone
Acridine
Multicomponent reactions
1. Introduction
heating in organic solvents [9], in water catalyzed by TEBAC
[10], under microwave irradiation [11], and using ionic
Recently, multicomponent reactions (MCRs) have been
considered asa superior syntheticstrategy [1]. The MCRsare
veryflexible, atom economic in nature, and proceed through
a sequence of reaction equilibria, yielding the target product
[2]. Moreover, these transformations combine classical
concerns such as efficiency, selectivity, molecular comple-
xity and diversity [3,4]. The acridine derivatives have been
known first to be used as pigments and dyes since the 19th
century [5]. A range of acridines continue to be used today
for the treatment of actuelekaemia (amsacrine) [6], as
anticancer agents (ledakrin) [7]. To date, ranges of acridine
have been reported with a range of chemical and physical
properties. Their utility in the pharmaceutical industry has
also been reported [8]. A number of methods have been
developed for the synthesis of acridine compounds contai-
ning 1,4-dihydropyridines, from dimedone, aldehyde and
different anilines or ammonium acetate via traditional
liquids are emerging as effective solvents for green
processes. In recent years -Proline has drawn much interest
in different organic reactions due to its experimental
simpilicity in water and organic solvents, -Proline has
shown considerable catalytic efficiency in different trans-
formations such as enamine based direct catalytic asym-
L
L
metric aldol condensation [12],
a-amination reaction [13],
Mannich reaction [14], Diels-Alder reaction [15], Knoeve-
nagel reaction [16], Micheal condensation [17], and as
excellent promoter for the copper-catalyzed coupling
reaction [18], as well as in solvent-free Biginelli reaction
[19], in unsymmetric Hantzsch reaction [20], for the
selective synthesis of 2-aryl-1-arylmethyl-1H-benzimida-
zoles from wide range of substituted o-phenylenediamines
and aldehydes [21], proline catalysis has emerged recently
as an efficient means of generating functionalized cyclo-
hexanes ad spirane products via Barbas three-component
cycloaddition [22]; proline has also been used as catalyst for
two-carbon homologation and in various MCRs in one-pot
[23]. The developing of new MCRs and improving known
MCRs are an area of considerable current interest. Herein,
we report a simple and facile multicomponent one-pot
* Corresponding author.
E-mail addresses: heravimr@yahoo.com, heravimr@gmail.com
(M.R. Poor Heravi).
1631-0748/$ – see front matter ß 2011 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
doi:10.1016/j.crci.2011.12.001

M.R. Poor Heravi, P. Aghamohammadi / C. R. Chimie 15 (2012) 448–453
449
Table 1
synthesis of substituted tetrahydrobenzo[c]acridin-8(7H)-
ones in high yields, using -Proline (15 mol%) as an
Multicomponent reaction of salicylaldehyde,
a
-naphthylamine and 5,5-
L
dimethylcyclohexane-1,3-dione(dimedone) in the presence of different
solvents and different catalyst percentagesa.
organocatalyst. Most of the above reported synthetic
methods for the synthesis of substituted tetrahydrobenzo[-
c]acridin-8(7H)-ones suffer from one or more drawbacks,
such as a hazardous reaction condition, complex work-
up and purification, strong acidic condition [24], high
temperature [25,26], use of toxic metal catalyst [27],
poor yields, occurrence of side reactions and expensive
reagents. Therefore, the development of a mild generalized
method to overcome these shortcomings still remains
an ongoing challenge for the synthesis of highly
substituted tetrahydrobenzo[c]acridin-8(7H)-ones for or-
ganic chemists.
Entry
Catalyst (mol %)
Solvent
Time (h)
Yieldb (%)
1
–
EtOH
72
72
72
72
72
72
72
8
5–6
5–6
Trace
Trace
Trace
Trace
N.R.c
55
2
–
MeOH
CHCl3
3
–
4
–
CH3CN
CH2Cl2
1,4-Dioxane
H2O
5
–
6
–
7
–
8
5
EtOH
9
10
15
20
15
15
15
15
15
15
EtOH
4
75
10
11
12
13
14
15
16
17
EtOH
1
95
EtOH
1
85
MeOH
CHCl3
12
12
12
12
12
48
75
35
2. Results and discussion
CH3CN
CH2Cl2
1,4-Dioxane
H2O
25
20
We report herein, for the first time, a simple, mild, and
expeditious synthesis of highly substituted tetrahydro-
benzo[c]acridin-8(7H)-ones in excellent yields employing
30
N.Rc
a
5,5-dimethylcyclohexane-1,3-dione(dimedone)/aldehyde/
thylamine(1:1:1).
a-naph-
L-Proline (15 mol%) as an organocatalyst at room
b
Isolated yield.
temperature (Scheme 1).
c
No reaction.
In order to standardize the reaction, salicylaldehyde
(1mmol),
a-naphthylamine (1 mmol), 5,5-dimethylcyclo-
hexane-1,3-dione(dimedone) (1 mmol) were dissolved in
ethanol and stirred at room temperature for 30 min. in the
absence of the catalyst which led to very poor yields (only
5–6%, as obtained in crude 1H NMR) of the substituted
tetrahydrobenzo[c]acridin-8(7H)-ones. We also tried dif-
ferent solvents under similar reaction conditions but no
appreciable increment in product yield was observed. Then
it was thought worthwhile to study the reaction I in the
secondly to the reaction passing via imine with lower
reactivity rather than iminium ion with -Proline with
much higher reactivity (via mechanism). The detailed
L
results of changing catalyst (
solvents are given in Table 1.
We next examined
L
-Proline) concentration and
a
wide variety of aldehydes
(both aromatic and aliphatic) with various substituents
to establish the catalytic importance of -Proline
L
presence of an organocatalyst like L-Proline. Use of 15 mol%
for this reaction. A wide range of ortho-, meta- and
para-substituted aromatic aldehydes undergo this
one-pot multicomponent synthesis with dimedone and
of the catalyst produced maximum yield (95%). A further
increase of the catalyst concentration does not increase the
yield. On the contrary, the reaction slows down on adding
more than 15 mol% of catalyst. The standard reaction was
also studied in the presence of glycine (15 mol %), when the
desired product was obtained after 72 h in only 10%
isolated yield. This lower yield could be attributed firstly to
the comparatively poor solubility of glycine in ethanol and
a
-naphthylamine to afford substituted tetrahydroben-
zo[c]acridin-8(7H)-ones in good yields. In all cases, we
observed the almost same performance towards this
cyclocondensation to give the desired product (4a–m)
(Table 2). Aliphatic aldehydes gave the corresponding
Scheme 1. L-Proline catalysed synthesis of substituted tetrahydrobenzo[c]acridin-8(7H)-ones.

450
M.R. Poor Heravi, P. Aghamohammadi / C. R. Chimie 15 (2012) 448–453
Table 2
Synthesis of highly tetrahydrobenzo[c]acridin-8(7H)-ones (4a–m) at room temperature using L
-Proline (15 mol %) as an organocatalysta.
Entry
R
Time (h)
Product
Yieldb (%)
Mp (oC)
Found
Reported
1
C6H5
1
4a
4b
4c
4d
4e
4f
95
91
92
92
97
95
93
95
96
97
88
87
89
257–258
212–214
206–207
221–223
289–290
281–283
228–229
218–219
231–233
276–277
187–189
191–192
195–197
258–259 [28,29]
2
4-CH3C6H4
4-CH3OC6H4
2-OHC6H4
4-ClC6H4
4-NO2C6H4
2-NO2C6H4
4-FC6H4
2-FC6H4
4-CF3C6H4
H
2
–
3
2
–
4
2
220–222 [30]
5
1
290–292 [28,29]
6
0.5
0.5
0.5
0.5
0.5
4
281–283 [31]
7
4g
4h
4i
–
–
–
–
–
–
–
8
9
10
11
12
13
4j
4k
4l
Me
4
CH(CH3)2
5
4m
a5,5-dimethylcyclohexane-1,3-dione(dimedone)/aldehyde/
a-naphthylamine (1:1:1).
b
Isolated yield.
O
N
H
NH2
O
Path I
O
R
C
O
(3)
O
HO
O
(2)
R
O
O
H2N
-H2O
-H2O
R
H
(1a-m)
C
B
O
-H2O
COOH
-
N
H
O
H
Path II
(2)
O
R
COOH
N
H
COOH
O
N
H
N
R
H
R
(4a-m)
(1a-m)
Scheme 2. A plausible mechanism for the formation of tetrahydrobenzo[c]acridin-8(7H)-ones, Pathway I-acid catalysis through intermolecular hydrogen
bonding. Pathway II-iminium catalysis.
tetrahydrobenzo[c]acridin-8(7H)-ones in lower yield
(25–35%) than aromatic aldehydes (90–98%). The reac-
tion profile is very clean and no side products are
formed. All the synthesized tetrahydrobenzo[c]acridin-
8(7H)-ones have been characterized on the basis of
elemental and spectral studies.
intermediate B via iminum catalysis which condenses with
the condensation product of amine and 5,5-dimethylcy-
clohexane-1,3-dione(dimedone) to form the intermediate
C which, on dehydration, gives the tetrahydrobenzo[c]a-
cridin-8(7H)-ones (4a–m).
A plausible mechanism for the
L
-Proline catalyzed
3. Conclusion
synthesis of highly substituted tetrahydrobenzo[c]acridin-
8(7H)-ones has been proposed (Scheme 2) in which the
reaction proceeds through two different pathways (Path-I
and Path-II). Path-I involves the activation of aldehydic
In conclusion, we have developed
efficient one-pot multicomponent methodology for the
synthesis of substituted tetrahydrobenzo[c]acridin-
a simple and
carbonyl oxygen by the acidic part of
L
-Proline through
8(7H)-ones (4a–m) catalyzed by 15 mol% L-Proline at
intermolecular H-bonding and subsequent condensation
with 5,5-dimethylcyclohexane-1,3-dione(dimedone) to
form the ene dione intermediate B. Path-II gives the same
room temperature. Simplicity of operation, high yields,
easy work-up, purification of compounds by non-
chromatography method (crystallization only) and wide

M.R. Poor Heravi, P. Aghamohammadi / C. R. Chimie 15 (2012) 448–453
451
range of substrate applicability are the key advantages of
this methodology.
2.45–2.74 (dd, 2H, C11-H), 4.32 (s, 3H, OCH3), 6.06 (s, 1H,
C7-H), 7.14–8.06 (m, 9H, Ar-H), 8.62 (d, 1H, J = 7.5, C6-H),
9.54 (s, 1H, NH). 13C NMR (DMSO-d6, 125 MHz):
d 26.31,
28.56, 30.54, 35.53, 40.09, 51.43, 64.87, 76.98, 81.21,
89.76, 104.65, 118.76, 120.65, 123.65, 123.97, 125.03,
127.43, 128.20, 129.43, 129.54, 130.43, 132.43, 144.32,
150.43, 155.43, 195.54. MS (EI), m/z (%) = 383 (M+, 70), 276
(92). HRMS (EI) Found: M+, 383.2109. C26H25NO2 requires
M+, 383.1921. Anal Calcd for C26H25NO2: C, 81.43; H, 6.57;
N, 3.65. Found: C, 81.21; H, 6.65; N, 3.86.
4. Experimental
4.1. General
All reagents were purchased from Merck. Aldehydes
were distilled before use. Melting points were determined
using a Linkman HF591 heating stage, used in conjunction
with a TC92 controller, and re-uncorrected. NMR spectra
were recorded using either a Brucker DRX500 machine at
room temperature. 1H, 13C NMR and 19FNMR spectra were
measured using DMSO-d6 as solvent. CHN analyses were
performed on Exeter Analytical Inc. ‘Model C-400 CHN
Analyzer’. Mass spectra were obtained using a Micro Mass
LCT machine in ES or EI mode. Infrared spectra were
measured on a Perkin Elmer Paragon 100 FT-IR spectro-
meter. All the reactions were monitored by TLC using
0.25 mm silica gel plates (Merck 60F254) UV indicator.
4.3.3. 10,10-Dimethyl-7-(4-nitrophenyl)-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4f)
0.378 g (95%); yellow solid; mp 241–242 8C. IR (KBr):
3306, 3065, 2897, 1643, 1567 (C = O), 1512, 1421, 1142,
819 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.18 (s, 3H, CH3),
1.41 (s, 3H, CH3), 2.08–2.34 (dd, 2H, C9-H), 2.56–2.83 (dd,
2H, C11-H), 5.89 (s, 1H, C7-H), 7.18–7.98 (m, 9H, Ar-H), 8.74
(d, 1H, J = 8.0, C6-H), 9.67 (s, 1H, NH). 13C NMR (DMSO-d6,
125 MHz):
d 27.21, 29.33, 31.43, 33.43, 42.49, 52.55, 66.54,
74.88, 88.76, 106.88, 117.43, 121.33, 122.21, 123.30,
124.21, 126.10, 129.11, 129.43, 129.42, 131.34, 133.54,
147.21, 153.65, 157.87, 196.33. MS (EI), m/z (%) = 398 (M+,
70), 196 (94). HRMS (EI) Found: M+, 398.2002. C25H22N2O3:
requires M+, 398.1611. Anal Calcd for C25H22N2O3: C,
75.36; H, 5.57; N, 7.03. Found: C, 75.30; H, 5.87; N, 7.21.
4.2. General procedure for the synthesis of substituted
tetrahydrobenzo[c]acridin-8(7H)-ones (4a–m)
In a 50 mL round bottom flask 5,5-dimethylcyclohe-
xane-1,3-dione (1 mmol), aldehyde (1 mmol) and
naphthylamine (1 mmol) were stirred in the presence of
15 mol% of -Proline in ethanol (2 mL) at room temperature
a-
4.3.4. 10,10-Dimethyl-7-(2-nitrophenyl)-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4g)
L
for the stipulated time (Table 2). The progress of the
reaction was monitored by TLC. After completion of the
reaction, the reaction mixture was diluted with water
(5 mL) and extracted with ethyl acetate (3 Â 10 mL). The
organic layer was dried over anhydrous Na2SO4, concen-
trated, and recrystallized from hot ethanol to afford the
pure product.
0.378 g (93%); yellow solid; mp 228–229 8C. IR (KBr):
3318, 3098, 2921, 1651, 1532 (C = O), 1505, 1434, 1154,
832 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.16 (s, 3H, CH3),
1.38 (s, 3H, CH3), 2.10–2.41 (dd, 2H, C9-H), 2.58–2.89 (dd,
2H, C11-H), 5.91 (s, 1H, C7-H), 7.14–8.03 (m, 9H, Ar-H),
8.82 (d, 1H, J = 8.0, C6-H), 9.83 (s, 1H, NH). 13C NMR
(DMSO-d6, 125 MHz): dd25.43, 30.23, 32.54, 36.42, 40.87,
53.33, 67.34, 77.41, 88.76, 119.55, 120.22, 121.66, 122.41,
124.09, 125.31, 125.87, 129.09, 129.65, 130.42, 132.76,
135.31, 148.43, 156.72, 158.34, 197.67. MS (EI), m/z
(%) = 398 (M+, 70), 196 (95). HRMS (EI) Found: M+,
398.1342. C25H22N2O3 requires M+, 398.1611. Anal Calcd
for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03. Found: C, 75.16;
H, 5.65; N, 7.09.
4.3. Characterization data of some representative compounds
4.3.1. 10,10-Dimethyl-7-(p-tolyl)-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4b)
0.334 g (91%); pale yellow solid; mp 212–214 8C. IR
(KBr): 3323, 3077, 2985, 1655, 1589 (C = O), 1523, 1446,
804 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.11 (s, 3H, CH3),
1.26 (s, 3H, CH3), 2.07–2.27 (dd, 2H, C9-H), 2.51–2.71 (dd,
2H, C11-H), 2.89 (s, 3H, CH3), 5.42 (s, 1H, C7-H), 7.11–8.10
4.3.5. 7-(4-Fluorophenyl)-10,10-dimethyl-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4h)
(m, 9H, Ar-H), 8.52 (d, 1H, J = 7.3, C6-H), 9.40 (s, 1H, NH). 13
NMR (DMSO-d6, 125 MHz): 27.23, 29.67, 32.64, 36.87,
C
0.352 g (95%); white solid; mp 218–219 8C. IR (KBr):
3315, 3069, 2973, 1640, 1531 (C = O), 1514, 1439, 1125,
836 mÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.10 (s, 3H, CH3),
1.29 (s, 3H, CH3), 2.08–2.34 (dd, 2H, C9-H), 2.45–2.81 (dd,
2H, C11-H), 5.92 (s, 1H, C7-H), 7.11–7.89 (m, 9H, Ar-H),
8.62 (d, 1H, J = 7.5, C6-H), 9.61 (s, 1H, NH). 13C NMR
(DMSO-d6, 125 MHz): d d 27.32, 31.03, 33.04, 37.23,
44.92, 58.41, 69.29, 78.44, 89.70, 119.02, 120.44, 120.89,
123.07, 124.26, 125.04, 125.89, 129.12, 129.54, 131.07,
133.52, 139.54, 149.43, 157.56, 159.42, 198.98. 19F NMR
(DMSO-d6, 470 MHz): À60.09. MS (EI), m/z (%) = 371 (M+,
70), 276 (92). HRMS (EI) Found: M+, 371.2101.
d
41.00, 50.56, 67.76, 87.98, 106.84, 119.85, 121.86, 122.72,
123.59, 124.05, 126.53, 128.19, 128.75, 128.92, 131.33,
133.05, 146.14, 152.87, 156.07, 194.01. MS (EI), m/z
(%) = 367 (M+, 70), 276 (95). HRMS (EI) Found: M+,
367.1904. C26H25NO requires M+, 367.1908. Anal Calcd
for C26H25NO: C, 84.98; H, 6.86; N, 3.81. Found: C, 90.05; H,
6.91; N, 3.65.
4.3.2. 7-(4-Methoxyphenyl)-10,10-dimethyl-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4c)
0.352 g (92%); white solid; mp 206–207 8C. IR (KBr):
3318, 3098, 2921, 1651, 1532 (C = O), 1505, 1434,
C
C
25H22FNO requires M+, 371.1703. Anal Calcd for
25H22FNO: C, 80.84; H, 5.97; N, 3.77. Found: C, 80.42;
1154,832 cmÀ1
.
1H NMR (DMSO-d6, 500 MHz): 1.13
(s, 3H, CH3), 1.31 (s, 3H, CH3), 2.03–2.25 (dd, 2H, C9-H),
H, 6.05; N, 3.73.

452
M.R. Poor Heravi, P. Aghamohammadi / C. R. Chimie 15 (2012) 448–453
4.3.6. 7-(2-Fluorophenyl)-10,10-dimethyl-9,10,11,12-
tetrahydrobenzo[c]acridin-8(7H)-one (4i)
46.65, 57.88, 68.98, 79.07, 80.54, 88.76, 110.65, 125.43,
129.28, 129.74, 131.43, 138.43, 149.33, 154.43, 156.76,
196.87. MS (EI), m/z (%) = 291 (M+, 70), 166 (79). HRMS (EI)
Found: M+, 291.180309. C20H21NO requires M+, 291.1608.
Anal Calcd for C20H21NO: C, 82.44; H, 7.26; N, 4.81. Found:
C, 82.06; H, 7.32; N, 4.43.
0.356 g (96%); pale yellow solid; mp231–233 8C. IR
(KBr): 3373, 3053, 2983, 1674, 1530 (C = O), 1520, 1423,
1145,823 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.12 (s, 3H,
CH3), 1.42 (s, 3H, CH3), 2.05–2.35 (dd, 2H, C9-H), 2.42–2.65
(dd, 2H, C11-H), 6.05 (s, 1H, C7-H), 7.21–8.11 (m, 9H, Ar-H),
8.74 (d, 1H, J = 8.0, C6-H), 9.65 (s, 1H, NH). 13C NMR
4.3.10. 7-Isopropyl-10,10-dimethyl-9,10,11,12-
(DMSO-d6, 125 MHz):
d
29.43, 32.43, 35.04, 39.54,
tetrahydrobenzo[c]acridin-8(7H)-one (4m)
44.56, 59.54, 68.65, 75.87, 89.43, 118.54, 121.44,
121.99, 123.65, 124.54, 125.43, 125.65, 129.43, 129.84,
131.37, 133.62, 141.54, 147.43, 154.58, 159.54, 197.87.
19F NMR (DMSO-d6, 470 MHz): À61.03. MS (EI), m/z
(%) = 371 (M+, 70), 276 (95). HRMS (EI) Found: M+,
371.165709. C25H22FNO requires M+, 371.1708. Anal
Calcd for C25H22FNO: C, 80.84; H, 5.97; N, 3.77. Found:
C, 80.61; H, 5.65; N, 3.83.
0.283 g (89%); pale yellow solid; mp 195–197 8C. IR
(KBr): 3318, 3098, 2921, 1651, 1532 (C = O), 1505, 1434,
1154,832 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.13 (s, 3H,
CH3), 1.31 (s, 3H, CH3), 2.03–2.25 (dd, 2H, C9-H), 2.45–2.74
(dd, 2H, C11-H), 3.45 (hep., 1H, CH), 4.56 (d, 6H, 2 Â CH3),
6.21 (s, 1H, C7-H), 7.16–8.02 (m, 5H, Ar-H), 8.72 (d, 1H,
J = 7.5, C6-H), 9.65 (s, 1H, NH). 13C NMR (DMSO-d6,
125 MHz):
d 26.31, 28.56, 30.54, 32.43, 33.27, 34.65,
35.53, 40.09, 51.43, 64.87, 76.98, 81.21, 89.76, 128.20,
129.43, 129.54, 131.04, 131.23, 143.32, 152.65, 153.43,
194.60. MS (EI), m/z (%) = 319 (M+, 70), 276 (90), 193 (45).
HRMS (EI) Found: M+, 319.1908. C22H25NO requires M+,
319.1932. Anal Calcd for C22H25NO: C, 82.72; H, 7.89; N,
4.38. Found: C, 82.56; H, 7.65; N, 4.66.
4.3.7. 10,10-Dimethyl-7-(4-(trifluoromethyl)phenyl)-
9,10,11,12-tetrahydrobenzo[c]acridin-8(7H)-one (4j)
0.408 g (97%); white solid; mp 276–277 8C. IR (KBr):
3332, 3076, 2971, 1651, 1522 (C = O), 1525, 1474, 1124,
822 cmÀ1. 1H NMR (DMSO-d6, 500 MHz): 1.11 (s, 3H, CH3),
1.23 (s, 3H, CH3), 2.05–2.32 (dd, 2H, C9-H), 2.43–2.84 (dd,
2H, C11-H), 5.97 (s, 1H, C7-H), 7.17–8.12 (m, 9H, Ar-H), 8.73
(d, 1H, J = 7.5, C6-H), 9.45 (s, 1H, NH). 13C NMR (DMSO-d6,
Acknowledgements
125 MHz):
d 26.34, 29.42, 31.54, 33.65, 42.76, 55.65, 68.65,
We thank the Payame Noor University (PNU), Tehran,
Iran, for financial support. Also, I express special thanks to
my wife (Dr. A. Hashemi) and my daughters (Niloofar
and Niki).
76.54, 85.43, 88.65, 105.43, 119.54, 121.43, 123.98, 124.54,
126.32, 127.08, 128.21, 129.21, 129.76, 131.32, 133.83,
137.96 (q, 1JCF = 255.76 Hz), 147.34, 156.43, 158.09, 198.56.
19F NMR (DMSO-d6, 470 MHz): À111.2. MS (EI), m/z
(%) = 421 (M+, 70), 276 (98). HRMS (EI) Found: M+,
421.2106. C26H22F3NO requires M+, 421.1709. Anal Calcd
for C26H22F3NO: C, 74.10; H, 13.52; N, 3.32. Found: C,
74.54, 13.21; H, 3.45.
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