Ultrasound-assisted one-pot synthesis of bis-azetidinones in the presence of zeolite

Article abstract of DOI:10.1002/jhet.1922

Sonochemical method is an innovative task for the sustainable chemical research industry. In this work, an attempt was made to synthesize bis-azetidin-2-ones (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j) by Staudinger reaction ([2 + 2] ketene-imine cycloadditi

Full text of DOI:10.1002/jhet.1922

August 2014 Ultrasound-Assisted One-pot Synthesis of Bis-azetidinones in the Presence
of Zeolite
E183
a
a
a
a
b
*
*
Venkateshwarlu Jetti, Praveen Chidurala, Ramakanth Pagadala, Jyotsna S. Meshram, and Chowdam Ramakrishna
aDepartment of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur 440033, Maharashtra, India
bSynthetic and Analytical Laboratory, Defence R&D Establishment, Nagpur 440001, Maharashtra, India
*
E-mail: venkatesh.jetti@gmail.com or drjsmeshram@rediffmail.com
Received September 3, 2012
DOI 10.1002/jhet.1922
Published online 22 April 2014 in Wiley Online Library (wileyonlinelibrary.com).
Sonochemical method is an innovative task for the sustainable chemical research industry. In this work, an
attempt was made to synthesize bis-azetidin-2-ones 2(a–j) by Staudinger reaction ([2 + 2] ketene-imine cycload-
dition reaction) in the presence of zeolite by using both conventional and under ultrasound irradiation. The
synthesized compounds have been elucidated on the basis of their elemental analysis and spectral data (IR, 1H
NMR, 13C NMR, and mass spectra) to evaluate its performance obtained under ultrasonic waves. It was observed
that complete conversion to azetidin-2-ones occurred in 1–2 h by sonochemical method and in 15–46 h by
conventional method. Finally, it has been observed that 2-azetidinones synthesis using sonochemical method is
an energy efficient and environmentally friendly technique over the conventional method.
J Heterocyclic Chem., 51, E183 (2014).
INTRODUCTION
has been focused on the synthesis and modification of b-lac-
tam ring to obtain compounds with diverse pharmacological
activities such as cholesterol absorption inhibitory activity,
human tryptase, thrombin and chymase inhibitory activity,
vasopressin V1a antagonist activity, antidiabetic, anti-inflam-
matory, antiparkinsonian, and anti-HIV activity [13–18].
They are also found to be a potent inhibitor of serine protease,
human leukocyte elastase, and human cytomegalovirus
protease enzyme [19–22] and are effective on central nervous
system; in recent past, these derivatives are also found to be
moderately active against several types of cancer [23]. The
biological activity of the b-lactam skeleton is generally
believed to be associated with the chemical reactivity of their
b-lactam ring; the oxo group is at 2nd position and on the
substituent especially at nitrogen of the 2-azetidinone ring.
In the last two decades, many heterocyclic compounds
from the benzothiazole series were synthesized and their
biological and pharmacological activity investigated.
The 2-aminobenzothiazole scaffold is one of the privileged
structures in medicinal chemistry [24]. Indeed, various exam-
ples featuring this particular scaffold have been prepared,
many exhibiting remarkable biological activities [25,26].
They were studied extensively for their antiallergic [27],
anti-inflammatory [28], antitumor [29–33], and analgesic
[34,35] activity. Considering the mechanism of action, it
was shown that benzothiazole derivatives act as tyrosine
kinase [36–39] and topoisomerase I and II inhibitors
[40,41]. Therefore, various benzothiazole compounds are
further of considerable interest for their diverse pharma-
ceutical uses.
A big challenge facing academia and industry is the
relationship of modern societies to the environment that
requires reinventing the manufacture and use of materials.
Synthetic methodologies nowadays should be designed to
use and generate substances that possess little or no
toxicity to human health and the environment. Several
reports have published on use of ultrasound as a process
intensification tool for numerous catalytic reactions as well
as in homogeneous and in heterogeneous reactions, and it
has proved to be a clean tool for improving yields and
decreasing reaction time [1].
As part of a program aimed at the synthesis of 2-azetidi-
none (b-lactam), we compare the Staudinger reaction under
ultrasonic and conventional method of their construction
from b-lactams. The synthesis of heterocylic compound
has always drawn the attention of chemist over the years
mainly because of their important biological properties.
Particularly, the role of b-lactam ring is endowed
with unique structure and potent antibacterial activity. The
2-azetidinone (b-lactam) ring system is the common
structural feature of a number of broad spectrum b-lactam
antibiotics, including penicillins, cephalosporins, carbape-
nems, nocardicins, monobactams, clavulanic acid, sulbac-
tams, and tazobactams, which have been widely used as
chemotherapeutic agents to treat bacterial infections and
microbial diseases [2–12]. Most of the researches up to early
1990s focused on synthesis of 2-azetidinones and study of
their antibacterial property. In recent years, renewed interest
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It is surprising to note that reports do not exist in the
simply by mixing 2-aminobenzothiazole with different
substituted aromatic aldehydes by using zeolite as acid
catalyst. To this reaction mixture was added TEA and a
solution of adipylchloride in DMF under ultrasound irradi-
ation. The characteristics of ultrasound could play a role in
generating cavitation in a process. Cavitation is the phe-
nomenon of sequential formation, growth, and collapse of
millions of microscopic vapor bubbles (voids) in a liquid
solution [42–44]. When the bubbles collapse rapidly, it cre-
ates highly localized temperatures and pressures inside the
cavities and hundreds of atmospheric pressures in several
nanoseconds, which allows many chemical reactions to
occur. And at the same time, fierce waves impact the
surface of the zeolite catalyst (Scheme 2).
When the bubbles collapse, it accelerates chemical reactions.
This support allows for easy separation of the solid catalyst and
product by simple filtration, and in optimal conditions, the
supported catalyst can be reused multiple times. This study
describes a successful approach for the synthesis of substituted
azetidin-2-ones using a laboratory ultrasonic cleaner.
literature for the synthesis of 2-aminobenzothiazole
containing bis-azetidinones. In this paper, we wish to report
herein our reports in the Staudinger reaction of 2-aminoben-
zothiazole containing bis-azetidinones that was synthesized
using conventional and ultrasound irradiation methods. The
effect of ultrasound on % yield, reaction time of synthesized
bis-azetidinones has been studied to understand the role of
ultrasound (ultrasonic energy) in the synthesis of azetidinone.
RESULTS AND DISCUSSION
Generally, organic reactions have been heated using
conventional heat transfer equipment such as oil baths,
sand baths, and heating jackets. These heating techniques
are, however, rather slow and a temperature gradient can
develop within the sample. In conventional method,
synthesis of azetidin-2-ones, reported so far, suffer from
one or more difficulties such as harsh reaction conditions,
poor yields, prolonged period, use of hazardous and often
expensive acid catalysts. We have employed to attain easy
and eco-friendly synthetic methodology for the synthesis
of substituted azetidin-2-ones using zeolite under sono-
chemical method.
In this paper, we synthesized azetidin-2-ones under
sonochemical as well as conventional method. By conven-
tional method, azetidin-2-ones were synthesized by stirring
in the presence of TEA and acid chloride for several hours.
In the present work, we report a facile ultrasound (sono-
chemical) synthesis of bis-azetidin-2-ones (Scheme 1).
The reaction was carried out for only 60–120 min, which
is far less than the conventional method (about 15–46 h)
(Scheme 1). In the present research, the whole process of
one-pot synthesis of bis-azetidin-2-ones took only 1–2 h,
which is substantially less than the reported methods, and
we achieved high yield in a much less reaction time.
Ultrasound-assisted synthesis of azetidin-2-ones 2(a–j)
are represented in (Scheme 1). Reactions were carried out
EXPERIMENTAL
Chemicals and apparatus. All the chemicals and solvents
were used AR grade without further purification. Melting points
were taken in an open capillary tube. IR spectra were recorded
1
on a Shimadzu Dr-8031 instrument (Japan). H NMR spectra of
the titled compounds were recorded on a Bruker-Avance
(300 MHz) spectrophotometer using DMSO solvent and TMS as
the internal standard. EI-MS spectra were determined on an
LCQ ion trap mass spectrometer (Thermo Fisher, San Jose, CA,
USA), equipped with an EI source. The reactions were
monitored, and the purity of products was checked out on
precoated TLC plates (Silica gel 60 F254, Merck), visualized
the spots under ultraviolet light and iodine chamber. Sonication
was performed in a “Spectralab model UCB 40D Ultrasonic
cleaner” with a frequency of 40 kHz and a nominal power
250 W. The reaction flask was located in the cleaner, where the
surface of reactants is slightly lower than the level of the water.
The reaction temperature was controlled by the addition or
removal of water from ultrasonic bath.
Scheme 1. Synthesis of azetedinones under ultrasound irradiation.
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Ultrasound-Assisted One-pot Synthesis of Bis-azetidinones in the Presence of Zeolite
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Scheme 2. Synthesis of azetidinones by classical method.
Synthesis of Schiff bases 1(a–j)
N-Benzylidenebenzothiazol-2-amine (1a). IR (KBr, cm–1):
1
1620 (-C═N-), H NMR (300 MHz, CDCl3) d (ppm) = 8.34 (s,
1H, CH═N), 6.6–7.7 (m, 9H, Ar-H); 13C NMR: d 121.8–148.5
for aromatic carbons, 159.07 (-HC═N-), 174.5 (-C═N-); mass
spectra: m/z = 238 (100%). Elemental analysis Calcd (found) for
C14H10N2S: C, 70.50 (70.44), H, 4.23 (4.29), N, 11.76 (11.70).
2-((Benzothiazol-2-ylimino)methyl)phenol (1b).
IR (KBr,
cmꢀ1): 1613 (-C═N-), 1H NMR (300 MHz, CDCl3) d (ppm) = 8.41
(s, 1H, CH═N), 6.7–7.8 (m, 8H, Ar-H), 12.56 (s, 1H, OH); 13C
NMR: d 111.1–156.7 for aromatic carbons, 160.5 (-HC═N-), 174.9
(-C═N-); Mass spectra: m/z= 254 (100%). Elemental analysis
Calcd (found) for C14H10N2OS: C, 66.12 (66.06), H, 3.96 (3.99),
N, 11.02 (11.08).
4-((Benzothiazol-2-ylimino)methyl)phenol (1c).
IR (KBr,
cmꢀ1): 1608 (-CH═N-), 1H NMR (300 MHz, CDCl3)
d
(ppm) = 8.36 (s, 1H, CH═N), 6.5–7.8 (m, 8H, Ar-H), 11.41 (s,
1H, OH); 13C NMR: d 112.4–154.3 for aromatic carbons, 161.5
(-HC═N-), 172.4 (-C═N-); mass spectra: m/z = 254 (100%).
Elemental analysis Calcd (found) for C14H10N2OS: C, 66.12
(66.07), H, 3.96 (3.92), N, 11.02 (11.08).
N-(4-(Dimethylamino)benzylidene)benzothiazol-2-amine
1
(1d). IR (KBr, cmꢀ1): 1615.7 (-CH═N-), H NMR (300 MHz,
CDCl3) d (ppm) = 8.61 (s, 1H, CH═N), 3.04 (s, 6H, N(CH3)2),
6.6–7.9 (m, 8H, Ar-H); 13C NMR: d 40.54 {N(CH3)2}, 115.2–
151.26 for aromatic carbons, 160.52 (-HC═N-), 171.24 (-C═N-);
mass spectra: m/z = 281 (100%). Elemental analysis Calcd (found)
for C16H15N3S: C, 68.30 (68.36), H, 5.37 (5.31), N, 14.93 (14.98).
Synthesis of Schiff base by ultrasound method 1(a–j). The
reaction was carried out in spectra lab model UCB 40D ultrasonic
cleaner. A 0.04 mol 2-aminobenzothiazole, 0.04 mol aromatic
aldehyde, and ethanol were taken in a Pyrex flask (50 mL). The
reaction mixture was irradiated in the water bath of an
ultrasonic cleaner for the period as indicated in Table 1. The
progress of the reaction was monitored by TLC. The reaction
mixture was poured into crushed ice. The precipitate was
separated by filtration, washed with water, and recrystallized
from ethanol to obtain 1(a–j). The crude product obtained was
purified by n-hexane and EtOAc.
General procedure for the synthesis of Schiff base by classical
method 1(a–j). A quantity of 0.04 mol of 2-aminobenzothiazole,
0.04 mol aromatic aldehyde (2), and 2–3 drops of acetic acid in
20 mL of ethanol was refluxed for 120–180 min. The completion
of reaction was monitored by TLC. After completion of the
reaction, the residue was stirred with ice cold water; solid deposit
was collected by filtration and dried. The crude product obtained
was purified by n-hexane and EtOAc (Table 2).
N-(4-Methoxybenzylidene)benzothiazol-2-amine (1e).
IR
1
(KBr, cmꢀ1): 1627.6 (-CH═N-), H NMR (300 MHz, CDCl3) d
(ppm) = 8.46 (s, 1H, CH═N), 3.90 (s, 3H, OCH3), 6.6–7.6 (m,
8H, Ar-H); 13C NMR: d 57.41 (OCH3) 113.44–156.8 for
aromatic carbons, 162.5 (-HC═N-), 173.41 (-C═N-); mass
spectra m/z = 268 (100%). Elemental analysis Calcd (found) for
C15H12N2OS: C, 67.14 (67.08), H, 4.51 (4.57), N, 10.44 (10.39).
3-((Benzothiazol-2-ylimino)methyl)phenol (1f).
IR (KBr,
1
cmꢀ1): 1616 (-C═N-), H NMR (300 MHz, CDCl3) d (ppm) = 8.5
(s, 1H, CH═N), 6.7–7.7 (m, 8H, Ar-H), 10.92 (s, 1H, OH); 13C
NMR: d 115.2–158.8 for aromatic carbons, 160.3 (-HC═N-), 176.5
(-C═N-); mass spectra: m/z= 254 (100%). Elemental analysis Calcd
(found) for C14H10N2OS: C, 66.12 (66.16), H, 3.96 (3.89), N,
11.02 (11.09).
Table 1
Time and yield comparison between classical and ultrasound irradiation 1(a–j).
Ultrasound method
Classical method
Compound
R
Reaction time (min)
Yield (%)a
Reaction time (min)
Yield (%)a
mp (ꢁC)
1a
1b
1c
1d
1e
1f
1g
1h
1i
C6H5
70
45
65
50
75
45
90
85
40
60
91
86
93
85
94
90
95
90
88
85
145
125
140
130
150
125
180
165
120
135
65
64
62
65
59
57
61
60
63
65
132
139
142
174
167
140
165
169
172
134
o-OHC6H4
p-OHC6H4
p-N(Me)2C6H4
p-OCH3C6H4
m-OHC6H4
m-ClC6H4
p-ClC6H4
p-NO2C6H4
m-CH3C6H4
1j
aIsolated yields.
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Table 2
Time and yield comparison between classical and ultrasound irradiation 2(a–j).
Ultrasound method
Classical method
Compound
R
Reaction time (min)
Yield (%)a
Reaction time (h)
Yield (%)a
mp (ꢁC)
2a
2b
2c
2d
2e
2f
2g
2h
2i
C6H5
90
80
60
110
90
80
110
120
60
89
92
85
90
93
87
88
90
85
87
35
27
15
42
36
28
41
46
18
27
63
68
67
71
61
62
65
70
60
64
139
148
145
172
162
142
158
156
170
140
o-OHC6H4
p-OHC6H4
p-N(Me)2C6H4
p-OCH3C6H4
m-OHC6H4
m-ClC6H4
p-ClC6H4
p-NO2C6H4
m-CH3C6H4
2j
80
aIsolated yields.
N-(3-Chlorobenzylidene)benzothiazol-2-amine (1g). IR (KBr,
cmꢀ1): 1619 (-C═N-), 1H NMR (300MHz, CDCl3) d (ppm) = 8.35
(s, 1H, CH═N), 6.7–7.6 (m, 8H, Ar-H); 13C NMR: d 113.8–159.3
for aromatic carbons, 162.9 (-HC═N-), 174.8 (-C═N-); mass
spectra: m/z= 272 (100%). Elemental analysis Calcd (found) for
C14H9ClN2S: C, 61.65 (61.60), H, 3.33 (3.29), N, 10.27 (10.31).
N-(4-Chlorobenzylidene)benzothiazol-2-amine (1h). IR (KBr,
cmꢀ1): 1617.5 (-C═N-), 1H NMR (300 MHz, CDCl3) d (ppm) = 8.5
(s, 1H, CH═N), 6.5–7.7 (m, 8H, Ar-H); 13C NMR: d 116.2–158.1
for aromatic carbons, 161.4 (-HC═N-), 171.2 (-C═N-); mass
spectra: m/z= 272 (100%). Elemental analysis Calcd (found) for
C14H9ClN2S: C, 61.65 (61.61), H, 3.33 (3.38), N, 10.27 (10.23).
solution were added triethylamine (0.05mol) and a solution of
adipylchloride (0.02 mol) in DMF (5 mL). The reaction mixture
was irradiated for ~60–120min. The completion of the reaction
was monitored by TLC. After the irradiation was over, the
reaction mixture was cooled and added into water. After filtering
the zeolite particles, the obtained solid product was separated and
purified from ethyl acetate and n-hexane.
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-phenylazetidin-
2-one) (2a). IR (KBr, cmꢀ1): 1759 (C═O b-lactam), 1365 (C-N);
1H NMR (300 MHz, CDCl3) d (ppm) = 1.75 (d, 4H, -CH2-CH2-); 5.0
(m, 2H, >C-C═O); 4.3 (d, 2H, >C-N<); 7.2–8.2 (m, 18H, Ar-H);
13C NMR: d 29.2 ((-CH2), 46.2 (-CH2-C═O), 62.4 (>CH-N<),
166 (N═C<), 168 (>C═O), 120, 122.1, 126, 126.9, 127.2, 128.7,
129.1, 139.1, 151.8 for aromatic carbons; mass spectra, m/z =586
(M+, 100%), elemental analysis: Calcd (found): C, 69.60 (69.64);
H, 4.47 (4.41); N, 9.55 (9.61).
N-(4-Nitrobenzylidene)benzothiazol-2-amine (1i).
IR (KBr,
cmꢀ1): 1614.3 (-C═N-), 1H NMR (300 MHz, CDCl3)
d
(ppm) = 8.42 (s, 1H, CH═N), 6.6–7.8 (m, 8H, Ar-H), ; 13C
NMR: d 111.5–157.3 for aromatic carbons, 163.4 (-HC═N-),
175.1 (-C═N-); mass spectra: m/z= 283 (100%). Elemental analysis
Calcd (found): for C14H9N3O2S: C, 59.35 (59.39), H, 3.20 (3.16),
N, 14.83 (14.75).
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(2-hydroxyphenyl)
azetidin-2-one) (2b). IR (KBr, cmꢀ1): 1758 (C═O b-lactam), 1366
1
(C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.78 (d, 4H, -CH2-
N-(3-Methylbenzylidene)benzothiazol-2-amine (1j). IR (KBr,
CH2-); 5.2 (m, 2H, O═C-CH<); 4.4 (d, 2H, >N-CH<); 7.2–8.2
(m, 16H, Ar-H); 12 (s, 2H, Ar-OH); 13C NMR: d 27.2 (-CH2), 49
(-CH2-C═O), 62.9 (>CH-N<), 163.4 (N═C<), 166.7 (>C═O),
116.1, 117.8, 121.9, 122.3, 126, 126.7, 129.9, 130.8, 152, 159 for
aromatic carbons; mass spectra, m/z=618 (M+, 100%), elemental
analysis: Calcd (found): C, 66 (66.2); H, 4.24 (4.20); N, 9.06 (9.02).
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(4-hydroxyphenyl)
cmꢀ1): 1615.8 (-C═N-), 1H NMR (300 MHz, CDCl3)
d
(ppm) = 8.3 (s, 1H, CH═N), 6.6–7.6 (m, 8H, Ar-H), 3.06 (s,
3H, Ar-CH3); 13C NMR: d 112.2–156.7 for aromatic carbons,
160.9 (-HC═N-), 172.1 (-C═N-); mass spectra: m/z= 253 (100%).
Elemental analysis Calcd (found): for C15H12N2S: C, 71.40 (71.36),
H, 4.79 (4.74), N, 11.10 (11.15).
azetidin-2-one) (2c).
IR (KBr, cmꢀ1): 1759 (C═O b-lactam),
Synthesis of bis-azetidinone (2a–j)
General procedure for the synthesis of substituted bis-azetidin-2-
1
1366 (C-N); H NMR (300 MHz, CDCl3) d (ppm)= 1.8 (d, 4H,
-CH2-CH2-); 5.2 (m, 2H, O═C-CH<); 4.2 (d, 2H, >N-CH<);
7.2–8.2 (m, 16H, Ar-H); 11.45 (s, 2H, Ar-OH); 13C NMR: d 28.1
(-CH2), 48.2 (-CH2-C═O), 63.5 (>CH-N<), 163.1 (N═C<), 167
(>C═O), 116.6, 118.1, 121.6, 122.8, 125.6, 126.2, 129.6, 131.4,
152.2, 158.1 for aromatic carbons; mass spectra, m/z = 618 (M+,
100%), elemental analysis: Calcd (found): C, 66 (66.2); H, 4.24
(4.32); N, 9.06 (9.01).
one by classical method 2(a–j).
The appropriate Schiff base
(0.04 mol) and triethylamine (0.05 mol) were stirred in anhydrous
dichloromethane, whereas a solution of adipylchloride (0.02 mol) in
dry dichloromethane was added drop wise. The reaction mixture
was stirred for 15–46 h. The completion of the reaction
was monitored by TLC. The reaction mixture was washed with
water and dried over sodium sulfate. The products that were
obtained after removing the solvent were purified from ethyl acetate
and n-hexane.
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(4-dimethylamino)
phenyl)azetidin-2-one) (2d). IR (KBr, cmꢀ1): 1756 (C═O b-lactam),
1
Synthesis of bis-azetidin-2-one base by ultrasound method
1366 (C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.63 (d, 4H,
2(a–j).
The reaction was carried out in spectralab model
-CH2═CH2-); 5.1 (m, 2H, O═C-CH<); 4.3 (d, 2H, >N-CH<);
7.2–8.2 (m, 16H, Ar-H); 3.06 (s, 12H, (N(CH3)2)); 13C NMR: d
41.3 (N(CH3)2), 26.9 (-CH2), 48 (-CH2-C-O), 62.4 (>CH-N<),
163.1 (N═C<), 166.2 (>C═O), 115.8, 117.9, 122.0, 121.9, 126,
UCB 40D ultrasonic cleaner. A 0.04 mol 2-aminobenzothiazole
(1), 0.04 mol aromatic aldehyde (2), and zeolite (montmorillonite
K-10) (0.2 g) were stirred with glass rod in DMF (20 mL). To this
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Ultrasound-Assisted One-pot Synthesis of Bis-azetidinones in the Presence of Zeolite
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126.2, 129.1, 130.3, 151.7, 159.2 for aromatic carbons; mass spectra,
m/z=618 (M+, 100%), elemental analysis: Calcd (found): C, 66
(66.4); H, 4.24 (4.27); N, 9.06 (9.01).
CONCLUSION
In summary, we report the synthesis of different substi-
tuted bis-2-azetidinones via Staudinger cycloaddition
between keten and Schiff base that was performed in
milder conditions under ultrasonic irradiation in the pres-
ence of zeolite that was of a high product yield and
enhance product purity with a shorter reaction time, easier
work-up, and environmentally friendly character compared
with previous conventional synthetic methods in the litera-
ture. Hence, the present method is an ample scope for
further study in developing these as good lead one-pot
methodology.
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(4-methoxyphenyl)
azetidin-2-one) (2e). IR (KBr, cmꢀ1): 1758 (C═O b-lactam), 1366
1
(C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.54 (d, 4H, -CH2-
CH2-); 5.2 (m, 2H, O═C-CH<); 4.68 (d, 2H, >N-CH<); 7.2–8.2
(m, 16H, Ar-H); 3.93 (s, 6H, OCH3); 13C NMR: d 56 (-CH3), 28.4
(-CH2), 45.5 (-CH2-C═O), 61 (>CH-N<), 164.5 (N═C<), 168.3
(>C═O), 117.9, 120.3, 122, 125, 126.5, 127.5, 129.9, 131.1,
153.2, 162 for aromatic carbons; mass spectra, m/z = 646 (M+,
100%), elemental analysis: Calcd (found): C, 66.85 (66.75); H,
4.68 (4.7); N, 8.66 (8.59).
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(3-hydroxyphenyl)
azetidin-2-one) (2f).
IR (KBr, cmꢀ1): 1745 (C═O b-lactam),
1
1353 (C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.72 (d, 4H,
-CH2-CH2-); 5.2 (m, 2H, O═C-CH<); 4.31 (d, 2H, >N-CH<);
7.2–8.2 (m, 16H, Ar-H); 10.89 (s, 2H, Ar-OH); 13C NMR: d 27.4
(-CH2), 48.4 (-CH2-C═O), 61.7 (>CH-N<), 163 (N═C<), 165.9
(>C═O), 116.4, 117.4, 122.4, 122.1, 126.2, 126.3, 129.3, 130.5,
152.1, 159 for aromatic carbons; mass spectra, m/z = 618 (M+,
100%), elemental analysis: Calcd (found): C, 66 (66.7); H, 4.24
(4.19); N, 9.06 (9.01).
Acknowledgments. We greatly acknowledge the head of the
Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur
University, Nagpur (India) for laboratory facilities and the director
of SAIF Chandigarh (India) for providing necessary spectral data
of compounds.
3,30-(Ethane-1,2-diyl)bis(1-(benzothiazol-2-yl)-4-(3-chlorophenyl)
REFERENCES AND NOTES
azetidin-2-one) (2g).
IR (KBr, cmꢀ1): 1760 (C═O b-lactam),
1
1364 (C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.61 (d, 4H,
-CH2-CH2-); 5.1 (m, 2H, O═C-CH<); 4.6 (d, 2H, >N-CH<);
7.2–8.2 (m, 16H, Ar-H); 13C NMR: d 28.1 (-CH2), 46.9 (-CH2-
C═O), 61.1 (>CH-N<), 165.1 (N═C<), 168.4 (>C-O), 118.9,
119.8, 122.5, 124.6, 125.9, 127.5, 129.4, 131.6, 153, 161.1
for aromatic carbons; mass spectra, m/z= 654 (M+, 100%),
elemental analysis: Calcd (found): C, 62.29 (62.21); H, 3.69 (3.72);
N, 8.55 (8.59).
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1
1347 (C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.59 (d, 4H,
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1
(C-N); H NMR (300 MHz, CDCl3) d (ppm) = 1.79 (d, 4H, -CH2-
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2-one) (2j). IR (KBr, cmꢀ1): 1746 (C═O b-lactam), 1354 (C-N);
1H NMR (300 MHz, CDCl3) d (ppm) = 1.59 (d, 4H, -CH2-CH2-);
5.0 (m, 2H, O═C-CH<); 4.61 (d, 2H, >N-CH<); 7.2–8.2
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