A rapid, four-component synthesis of functionalized thiazoles

Article abstract of DOI:10.2174/138620711796957134

An efficient synthesis of 2-(dialkylamino)-4-phenyl)-1,3-thiazol-5-yl) (phenyl)methanone using acid chlorides, secondary amines, 2-bromoacethophenone and ammonium thiocyanate is described.

Full text of DOI:10.2174/138620711796957134

824
Combinatorial Chemistry & High Throughput Screening, 2011, 14, 824-828
A Rapid, Four-Component Synthesis of Functionalized Thiazoles
Maryam Sabbaghan*,1, Mostafa Alidoust1 and Zinatossadat Hossaini2
1Chemistry Department, Faculty of Sciences, Shahid Rajaee Teacher Training University, P.O. Box 16785-163, Tehran,
Iran
2Department of Chemistry, Qaemshahr Branch, Islamic Azad University, P.O. Box 163, Qaemshahr, Iran
Abstract: An efficient synthesis of 2-(dialkylamino)-4-phenyl)-1,3-thiazol-5-yl)(phenyl)methanone using acid chlorides,
secondary amines, 2-bromoacethophenone and ammonium thiocyanate is described.
R''
R''
R
H
N
N
O
1) acetone
2) H2O
NH4SCN
+
R
+
+
Br
R'
R'
N
R'
Cl
S
O
O
R'
Keywords: Thiazole, Hantzsch synthesis, 2-Bromoacethophenone, Aroyl isothiocyanate, Secondary amine.
1. INTRODUCTION
being the Hantzsch’s synthesis, in which an ꢀ-halocarbonyl
compound is condensed with a thioamides, thioureas,
thiocarbamic acids, or dithiocarbamic acids [12-14].
The thiazole ring system is commonly found in many
pharmaceutically important molecules. Numerous natural
products containing this heterocycle have been isolated and
exhibit significant biological activities such as cytotoxic,
immunosuppressive, antifungal, and enzyme inhibitory
activity [1]. Moreover, among the different aromatic
heterocycles, thiazoles occupy a prominent position in the
drug discovery process [2] and this ring structure is found in
several marketed drugs.
As part of our current studies on the development of new
routes in heterocyclic synthesis [15-18], we describe an
efficient one-pot method for the synthesis of functionalized
thiazoles.
2. RESULTS AND DISCUSSION
The reaction of ammonium thiocyanate 1, benzoyl
chlorides 2 and secondary amines 3 in the presence of 2-
Aminothiazoles are known to be ligands of estrogen
receptors [3] as well as a novel class of adenosine receptor
antagonists [4]. Other analogues are used as fungicides,
inhibiting in vivo growth of Xanthomonas, as an ingredient
of herbicides or as schistosomicidal and anthelmintic drugs
[5] Fanetizole, a derivative of 2-aminothiazole is an anti-
inflammatory agent (Fig. 1).
bromoacethophenone
4
led to 2-(Dialkylamino)-4-
phenylthiazol-5-yl) (phenyl) methanone 5 in excellent yields
(Scheme 1). Structures of compounds 5a-5m were assigned
1
by IR, H NMR and 13C NMR data and elemental analysis.
For example, the 1H NMR spectrum of 5a in CDCl3ꢀ
exhibited triplet and quartet (ꢀ = 1.31 and 3.61) for ethyl,
and characteristic multiplets (ꢀ = 7.39-7.76) for the aromatic
protons. The proton-decoupled 13C NMR spectrum of 5a
showed 14 distinct resonances in agreement with the
proposed structure. The 13C NMR spectra of the 2-
(dialkylamino)-4-phenyl)-1,3-thiazol-5-yl)(phenyl)methanone
ring system of 5a showed signals at ꢀ = 135.2 (C), 160.0 (C)
and 170.5 (C) ppm. The carbonyl group resonance in
spectrum appears at 188.7 ppm. The 1H NMR and 13C NMR
spectra of 5b–m were similar to those for 5a except for the
amine moieties, which exhibited characteristic resonances in
the appropriate regions of the spectrum. Partial assignments
of these resonances are given in Experimental section.
H
NH2
N
N
N
R1
S
S
R2
Fanitazole
2-Aminothiazole
Fig. (1).
In addition, thiazoles are also synthetic intermediates and
common substructures in numerous biologically active
compounds. Thus the thiazole nucleus has been much
studied in the field of organic and medicinal chemistry [6].
Several methods for the synthesis of thiazole derivatives
have been developed [7-11], the most widely used method
Mechanistically, the reaction starts with the formation of
aroyl isothiocyanate 6, followed by addition of amine 3 to
generate the thiourea derivative 7. Subsequent nucleophilic
alkylation of
7
with 2-bromoacethophenone yields
intermediate 8. Intermediate 8 undergoes HBr elimination
and subsequent enolization to generate 10, which undergoes
intramolecular cyclization reaction to form the heterocyclic
*Address correspondence to this author at the Chemistry Department,
Faculty of Sciences, Shahid Rajaee Teacher Training University, P.O. Box
16785-163, Tehran, Iran; Tel: +98-21-22970003; Fax: +98-21-22970033;
E-mail: sabbaghan@srttu.edu, msaba16us@yahoo.com
1386-2073/11 $58.00+.00
© 2011 Bentham Science Publishers

A Rapid, Four-Component Synthesis of Functionalized Thiazoles
Combinatorial Chemistry & High Throughput Screening, 2011, Vol. 14, No. 9 825
R
R''
R''
O
H
N
1) acetone
2) H2O
N
NH4SCN
Br
+
R'
+
Cl +
N
R'
S
R'
O
O
R'
R
R
H
H
H
H
H
R'
Et
(CH2)4
(CH2)5
(CH2)2O(CH2)2
(CH2)5
(CH2)5
Et
Et
Me
(CH2)4
(CH2)2O(CH2)2
(CH2)4
(CH2)2O(CH2)2
5
a
b
c
d
e
f
R''
4
a H
b
c
d
Yeild (%)
R''
R
H
OMe
NO2
Br
3 R'
2
a
1
a
b
c
d
e
H
H
H
H
Me
Et
(CH2)4
(CH2)5
84
94
90
OMe
Cl
Br
b
c
d
89
(CH2)2O(CH2)2
OMe
H
H
Cl
92
94
90
95
89
85
87
90
87
OMe
OMe
OMe
NO2
NO2
NO2
Br
g
h
i
j
Br
Br
Br
Br
Br
k
l
m
Br
Scheme 1. Synthesis of thiazoles (5).
intermediate 11. Subsequent loss of water affords thiazoles 5
(Scheme 2).
3. CONCLUSION
In conclusion, we have developed a convenient, efficient,
and one-pot route for synthesis of functionalized thiazoles
from ammonium thiocyanate, acid chlorides, and secondary
The reaction product easily precipitates.
R''
R' R'
O
O
N
+ 4
+ 3
H
N
H
C
N
C
S
+ 2
N
1
S
R'
O
R
R
R'
N
S
Br
R'
O
6
7
8
R''
R''
Enolization
- HBr
N
N
R'
O
R'
O
R'
R'
N
N
S
S
R'
R'
O
OH
9
10
R''
R''
R'
R'
OH
S
O
N
N
R'
R'
5
N
N
S
O
HO
R'
R'
11
Scheme 2. Proposed mechanism for the one-pot thiazole synthesis.

826 Combinatorial Chemistry & High Throughput Screening, 2011, Vol. 14, No. 9
Sabbaghan et al.
amines, in the presence of 2-bromoacethophenone. The
advantage of the present procedure is that the reaction is
performed under neutral conditions by simple mixing of the
starting materials in a sequential manner. Short reaction
time, operational simplicity, and high yields are the salient
features of the present procedure. This is a very fortunate
outcome since the reaction can then be easily workup
without requiring costly purification procedures such as
column chromatography. Since the experimental conditions
for this reaction are quite straightforward, small libraries of
thiazoles will be readily accessible by parallel synthesis with
the possibility that these compounds may display interesting
biological properties, which would deserve further
investigations.
2.36 (m, 4 H, 2 CH2), 3.60 (broad s, 4 H, CH2NCH2), 7.01-
7.11 (m, 5 H, 5 CH), 7.16-7.32 (m, 3 H, 3 CH), 7.42 (d, 2 H,
3J = 7.0, 2 CH).13C NMR: 25.7 (2 CH2), 49.8 (CH2NCH2),
122.5 (C), 127.5 (2 CH), 127.6 (2 CH), 128.5 (CH), 129.0 (2
CH), 129.9 (2 CH), 131.0 (CH), 135.0 (C), 138.5 (C), 160.0
(C), 168.5 (C), 188.6 (C=O). Anal. Calcd for C20H18N2OS
(334.43): C 71.83, H 5.42, N 8.38, Found: C 71.71, H 5.31,
N 8.31.
5.3. Phenyl(4-Phenyl-2-Piperidin-1-yl-1,3-Thiazol-5-yl)Methan-
one (5c)
Yellow powder, Yield: 0.62 g (90%), m.p. 114-116 °C.
IR (KBr) (ꢀmax/cmꢁ1): 1706, 1634, 1339 cm-1. 1H NMR: 1.74
(broad s, 6 H, 2 CH2), 3.71-3.75 (m, 4 H, CH2NCH2), 7.03-
7.14 (m, 4 H, 4 CH), 7.20-7.33 (m, 4 H, 4 CH), 7.42 (d, 2 H,
3J = 7.2, 2 CH). 13C NMR: 23.9 (CH2), 25.3 (2 CH2), 49.7 (2
CH2), 119.9 (C), 127.6 (2 CH), 127.6 (2 CH), 128.8 (CH),
129.1 (2 CH), 130.2 (2 CH), 131.2 (CH), 134.5 (C), 135.2
(C), 160.9 (C), 172.8 (C), 188.1 (C=O). Anal. Calcd for
C21H20N2OS (348.46): C 72.38, H 5.79, N 8.04, Found: C
72.43, H 5.64, N 8.01.
4. MATERIAL AND METHODS
2-bromoacethophenone, acid chlorides, ammonium
thiocyanate, and secondary amines were obtained from
Merck and were used without further purification. Melting
points were obtained uncorrected using an Electrothermal-
9100 apparatus. IR spectra were recorded with a panorama
ABB FTLA-2000 spectrometer. 1H and 13C NMR spectra
were recorded with a Bruker DRX-250 Avance instrument
using CDCl3 as the deuterated solvent at 250 and 62.5 MHz,
respectively [Include compound used as internal standard]; ꢀ
in parts per million, J in hertz.
5.4. (2-Morpholino-4-yl-4-Phenylthiazol-5-yl)(Phenyl)Methan-
one (5d)
Yellow powder, Yield: 0.62 g (89%), m.p. 131-133 °C.
IR (KBr) (ꢀmax/cmꢁ1): 1717, 1645, 1311 cm-1. 1H NMR: 3.66-
3.69 (m, 4 H, CH2NCH2), 3.84-3.88 (m, 4 H, CH2OCH2),
7.02-7.16 (m, 5 H, 5 CH), 7.21-7.31 (m, 3 H, 3 CH), 7.45 (d,
2 H, 3J = 7, 2 CH). 13C NMR: 48.1 (CH2NCH2), 66.4
(CH2OCH2), 122.9 (C), 127.7 (4 CH), 128.7 (CH), 129.2 (2
CH), 129.9 (2 CH), 131.4 (CH), 134.8 (C), 138.2 (C), 159.1
(C), 171.8 (C), 188.8 (C=O). Anal. Calcd for C20H18N2O2S
(350.43): C 68.55, H 5.18, N 7.99, Found: C 68.48, H 5.10,
N 7.92.
5. GENERAL PROCEDURE
To a stirred solution of ammonium thiocyanate (1) (0.15
g, 2 mmol) in acetone (15 mL) was added benzoyl chloride
(2) (2 mmol) in a round bottomed flask. The mixture was
refluxed for 5 min, removed from heat, and then a solution
secondary amine (3) (2 mmol) in acetone (5 mL) was added
slowly with a syringe. The mixture refluxed for 30 minutes.
After cooling to 0°C by means of an ice bath, water (20 mL)
was poured over the reaction mixture, then 2-
bromoacethophenone (2 mmol) was added. The resulting
solution was stirred for 30 min at room temperature. After
completion of the reaction (monitored by TLC), the
precipitate was collected by filtration and washed by cold
50% aqueous EtOH (5 mL) to afford 5.
5.5. (4-Methoxyphenyl)(4-Phenyl-2-Piperidin-1-yl-1,3-Thiazol-
5-yl)Methanone (5e)
Yellow powder, Yield: 0.69 g (92%), m.p. 138-140 °C.
IR (KBr) (ꢀmax/cmꢁ1): 1691, 1624, 1350, 1247 cm-1. 1H
NMR: 1.73 (broad s, 6 H, 2 CH2), 3.64-3.66 (m, 4 H,
3
CH2NCH2), 3.75 (s, 3 H, OCH3), 6.60 (d, 2 H, J = 7.8, 2
CH), 7.04-7.16 (m, 3 H, 3 CH), 7.35-7.38 (m, 2 H, 2 CH),
7.48 (d, 2 H, 3J = 7.8, 2 CH). 13C NMR: 23.9 (CH2), 25.2 (2
CH2), 49.5 (CH2NCH2), 55.3 (OCH3), 113.1 (2 CH), 127.6
(C), 127.7 (2 CH), 128.5 (CH), 129.4 (C), 130.0 (2 CH),
130.9 (C), 131.5 (2 CH), 160.0 (C), 162.2 (C), 171.3 (C),
187.5 (C=O). Anal. Calcd for C22H22N2O2S (378.48): C
69.81, H 5.86, N 7.40, Found: C 69.59, H 5.80, N 7.34.
5.1. [2-(Diethylamino)-4-Phenyl-1,3-Thiazol-5-yl](Phenyl)
Methanone (5a)
Yellow powder, yield: 0.56 g (84%), m.p. 130-132 °C. IR
1
(KBr) (ꢀmax/cmꢁ1): 1691, 1650, 1473, 1324 cm-1. H NMR:
1.31 (t, 6 H, 3J = 7.2, 2 Me), 3.62 (q, 4 H, 3J = 7.2, 2 NCH2),
7.00-7.11 (m, 4 H, 4 CH), 7.18-7.31 (m, 4 H, 4 CH), 7.43 (d,
3
2 H, J = 7.00, 2 CH). 13C NMR: 12.5 (2 Me), 45.6 (2
NCH2), 122.0 (C), 127.4 (2 CH), 127.5 (2 CH), 128.4 (CH),
129.0 (2 CH), 129.9 (2 CH), 130.9 (CH), 135.2 (C), 138.6
(C), 160.0 (C), 170.5 (C), 188.7 (C=O). Anal. Calcd for
C20H20N2OS (336.45): C 71.40, H 5.99, N 8.33, Found: C
71.12, H 5.43, N 8.21.
5.6. [4-(4-Methoxyphenyl)-2-Piperidin-1-yl-1,3-Thiazol-5-
yl](Phenyl)Methanone (5f)
Yellow powder, Yield: 0.71 g (94%), m.p. 132-134 °C.
IR (KBr) (ꢀmax/cmꢁ1): 1691, 1640, 1298 cm-1. 1H NMR: 1.74
(broad s, 6 H, 2 CH2), 3.71-3.75 (m, 4 H, CH2NCH2), 3.90
(s, 3 H, OMe), 6.57 (d, 2 H, 3J = 8.2, 2 CH), 7.1 (t, 2 H, 3J =
7.5, 2 CH), 7.2-7.29 (m, 3 H, 3 CH), 7.46 (d, 2 H, 3J = 7.5, 2
CH). 13C NMR: 24.0 (CH2), 25.8 (2 CH2), 50.1 (CH2NCH2),
54.2 (OCH3), 110.1 (2 CH), 127.1 (2 CH), 127.7 (2 CH),
128.4 (C), 129.9 (CH), 131.9 (2 CH), 132.5 (C), 138.0 (C),
5.2. Phenyl(4-Phenyl-2-Pyrrolidin-1-yl-Thiazol-5-yl)Methan-
one (5b)
Yellow powder, Yield: 0.62 g (94%), m.p. 157-158 °C.
IR (KBr) (ꢀmax/cmꢁ1): 1696, 1640, 1324 cm-1. 1H NMR: 2.07-

A Rapid, Four-Component Synthesis of Functionalized Thiazoles
Combinatorial Chemistry & High Throughput Screening, 2011, Vol. 14, No. 9 827
161.0 (C), 164.2 (C), 171.3 (C), 186.5 (C=O). Anal. Calcd
for C22H22N2O2S (378.48): C 69.81, H 5.86, N 7.40, Found:
C 69.68, H 5.81, N 7.35.
5.11. (4-Bromophenyl)[2-Morpholino 4-(4-Nitrophenyl)-
1,3-Thiazole-5-yl]Methanone (5k)
Yellow powder, yield: 0.82 g (87%); mp138-140°C; IR
1
(KBr) (ꢀmax/cmꢁ1): 1679, 1609, 1521 and 1472 cm-1. H
5.7. [2-(Diethylamino)-4-(4-Methoxyphenyl)-1,3-Thiazol-
5-yl](Phenyl)Methanone (5g)
NMR: 3.08-3.10 (m, 4 H, CH2NCH2), 3.74-3.78 (m, 4 H,
3
3
CH2OCH2), 7.17 (d, 2 H, J = 7.6, 2 CH), 7.25 (d, 2 H, J =
3
3
7.5, 2 CH), 7.37 (d, 2 H, J = 7.6, 2 CH), 7.97 (d, 2 H, J =
7.5, 2 CH). 13C NMR: 42.7 (CH2NCH2), 63.2 (CH2OCH2),
122.5 (2 CH), 125.3 (C), 129.6 (C), 130.5 (2 CH), 130.8 (4
CH), 131.6 (C), 140.9 (C), 146.9 (C), 156.5 (C), 171.4 (C),
185.9 (C=O). EI-MS: 476 (M++2, 10), 474 (M+, 10), 289
(85), 185 (100). Anal. Calcd for C20H16BrN3O4S (474.33): C,
50.64; H, 3.40; N, 8.86. Found: C, 50.58; H, 3.36; N, 8.79%.
Yellow powder, Yield: 0.66 g (90%), m.p. 112-113°C. IR
(KBr) (ꢀmax/cmꢁ1): 1691, 1645, 1334, cm-1. 1H NMR: 1.32 (t,
6 H, 3J = 7.2, 2 Me), 3.70 (q, 4 H, 3J = 7.2, 2 NCH2), 3.76 (s,
3
3
3 H, OMe), 6.60 (d, 2 H, J = 8.5, 2 CH), 7.08 (t, 1 H, J =
7.3, 1 CH), 7.24-7.39 (m, 4 H, 2 CH), 7.44 (d, 2 H, 3J = 7.3,
2 CH). 13C NMR: 12.5 (2 Me), 45.6 (2 NCH2), 54.1 (OMe),
110.2 (2 CH), 126.8 (2 CH), 127.4 (2 CH), 128.2 (C), 130.4
(CH), 132.2 (2 CH), 133.5 (C), 139.5 (C), 161.0 (C), 163.8
(C), 171.3 (C), 186.4 (C=O). Anal. Calcd for C21H22N2O2S
(366.48): C 68.82, H 6.05, N 7.64, Found: C 68.79, H 6.01,
N 7.53.
5.12. (4-Bromophenyl)[4-(4-Bromophenyl)2-(1-Pyrrolidino)-
1,3-Thiazole-5-yl]Methanone (5l)
Yellow powder, yield: 0.86 g (90%); mp 142-144°; IR
(KBr) (ꢀmax/cmꢁ1): 1658, 1603, 1531 and 1467 cm-1; 1H
NMR: 2.00-2.04 (m, 4 H, 2 CH2), 3.49 (m, 4 H, 2 CH2), 7.18
(d, 2 H, 3J = 7.8, 2 CH), 7.27 (d, 2 H, 3J = 7.6, 2 CH), 7.32
5.8. (4-Chlorophenyl)[2-(Diethylamino)-4-(4-Methoxyphenyl)-
1,3-Thiazol-5-yl]Methanone (5h)
3
3
(d, 2 H, J = 7.6, 2 CH), 7.36 (d, 2 H, J = 7.5, 2 CH). 13C
NMR: 25.7 (2 CH2), 50.2 (2 CH2), 122.6 (C), 125.2 (C),
129.9 (C), 130.9 (4 CH), 131.2 (2 CH), 132.1 (2 CH), 134.4
(C), 138.0 (C), 159.4 (C), 168.2 (C), 186.5 (C=O). Anal.
Calcd for C20H16Br2N2OS (492.23): C, 48.80, H, 3.28, N,
5.69. Found: C, 48.74; H, 3.19; N, 5.53%.
Yellow powder, Yield: 0.76 g (95%), m.p. 118-120°C. IR
(KBr) (ꢀmax/cmꢁ1): 1768, 1686, 1319, cm-1. 1H NMR: 1.32 (t,
6 H, 3J = 7.0, 2 Me), 3.62 (q, 4 H, 3J = 7.0, 2 NCH2), 3.75 (s,
3
3
3 H, OMe), 6.61 (d, 2 H, J = 8.5, 2 CH), 7.24 (d, 2 H, J =
3
3
8.5, 2 CH), 7.38 (d, 2 H, J = 8.5, 2 CH), 7.47 (d, 2 H, J =
8.5, 2 CH). 13C NMR: 13.4 (2 Me), 45.2 (2 NCH2), 53.2
(OMe), 110.1 (2 CH), 128.3 (2 CH), 128.2 (C), 129.9 (2
CH), 130.1 (C), 132.8 (2 CH), 134.0 (C), 137.1 (C), 156.3
(C), 160.6 (C), 161.3 (C), 184.2 (C=O). Anal. Calcd for
C21H21N2O2S (400.92): C 62.91, H 5.28, N 6.99, Found: C
62.89, H 5.21, N 6.94.
5.13. (4-Bromophenyl)[4-(4-Bromophenyl)-2-Pyrrolidino-
1,3-Thiazole-5-yl]Methanone (5m)
Yellow powder, yield: 0.88 g (87%); mp 152-154°C; IR
(KBr) (ꢀmax/cm-1): 1612, 1508, 1343 and 1300 cm-1; 1H
NMR: ꢀ 3.49-3.62 (m, 4 H, CH2NCH2), 3.74-3.78 (m, 4 H,
3
3
5.9. (4-Bromophenyl)[2-(Dimethylamino)-4-(4-Nitrophenyl)-
1,3-Thiazole-5-yl]Methanone (5i)
CH2OCH2), 7.21 (2 H, d, J = 7.6, 2 CH), 7.31 (2 H, d, J =
3
3
7.8, 2 CH), 7.34 (2 H, d, J = 7.8, 2 CH), 7.39 (2 H, d, J =
7.8, 2 CH). 13C NMR: 48.3 (CH2NCH2), 65.8 (CH2OCH2),
122.7 (C), 125.6 (C), 130.1 (C), 130.9 (2 CH), 131.0 (2 CH),
131.3 (2 CH), 131.7 (C), 132.1 (2 CH), 134.2 (C), 158.4 (C),
171.8 (C), 186.8 (C=O). Anal. Calcd for C20H16Br2N2O2S
(508.23): C, 47.27; H, 3.17; N, 5.51. Found: C, 47.18; H,
3.05; N, 5.47%.
Yellow powder, yield: 0.63 g (89%); mp 123-125°C; IR
(KBr) (ꢀmax/cm-1): 1678, 1420, 1321, and 1031 cm-1. 1H
3
NMR: 3.37 (s, 6 H, NMe2), 7.17 (d, 2 H, J = 7.8, 2 CH),
3
3
7.25 (d, 2 H, J = 8.2, 2 CH), 7.33 (d, 2 H, J = 8.2, 2 CH),
7.36 (d, 2 H, 3J = 7.8, 2 CH). 13C NMR: 32.4 (NMe2), 122.6
(2 CH), 125.2 (C), 130.9 (2 CH), 131.2 (2 CH), 132.1 (2
CH), 132.2 (C), 138.9 (C), 143.1 (C), 159.4 (C), 162.5 (C),
168.2 (C), 186.2 (C=O). Anal. Calcd for C18H14BrN3O3S
(432.29): C, 50.01; H, 3.26; N, 9.72. Found: C, 49.95; H,
3.18; N, 9.86%.
ACKNOWLEDGEMENT
This work was supported by the Research Council of
Shahid Rajaee Teacher Training University.
5.10. (4-Bromophenyl)[4-(4-Nitrophenyl)2-(1-Pyrrolidino-
1,3-Thiazole-5-yl]Methanone (5j)
DISCLOSURES
Part of information included in this article has been
previously published in ‘Molecular Diversity (2009) Volume
13, Number 3, 295-300’.
Yellow powder, yield: 0.78 g (85%); mp 143-145°C, IR
(KBr) (ꢀmax/cmꢁ1): 1674, 1625, 1537, and 1472 cm-1; 1H
NMR: 1.85-1. (m, 4 H, 2 CH2), 3.52-3.55 (m, 4 H,
3
3
CH2NCH2), 7.68 (d, 2 H, J = 8.0, 2 CH), 7.77 (d, 2 H, J =
3
3
REFERENCES
7.8, 2 CH), 8.12 (d, 2 H, J = 7.8, 2 CH), 8.42 (d, 2 H, J =
8.0, 2 CH). 13C NMR: 24.1 (2 CH2), 45.1 (2 CH2), 124.8 (2
CH), 125.8 (C), 129.6 (2 CH), 131.3 (2 CH), 132.2 (2 CH),
132.4 (C), 138.8 (C), 143.0 (C), 150.4 (C), 151.6 (C), 163.2
(C), 188.9 (C=O). Anal. Calcd for C20H16BrN3O3S (458.33):
C, 52.41; H, 3.52; N, 9.17. Found: C, 52.38; H, 3.45; N,
9.04%.
[1]
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Received: February 7, 2011
Revised: April 27, 2011
Accepted: June 1, 2011