Synthesis and in vitro antimicrobial screening of new azetidin-2-ones of 5-ethyl pyridine-2-ethanol

Article abstract of DOI:10.1002/jhet.1734

A new series of azetidinones is described in this paper; Schiff base (4a-o) were synthesized from 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde, which was used to synthesize azetidinones (5a-o), (6a-o), and (7a-o). The structures of the synthesized compou

Full text of DOI:10.1002/jhet.1734

May 2014
Synthesis and In Vitro Antimicrobial Screening of New Azetidin-2-ones of
775
5-Ethyl Pyridine-2-ethanol
Navin B. Patel, Hemant R. Patel, Faiyazalam M. Shaikh, and Dhanji Rajani
a
a
a
b
*
aDepartment of Chemistry, Veer Narmad South Gujarat University, Surat 395007, Gujarat, India
bMicrocare laboratory, Surat-395003, India
*
E-mail: drnavin@satyam.net.in
Received December 15, 2011
DOI 10.1002/jhet.1734
Published online 6 December 2013 in Wiley Online Library (wileyonlinelibrary.com).
A new series of azetidinones is described in this paper; Schiff base (4a–o) were synthesized from 4-[2-(5-
ethylpyridin-2-yl)ethoxy]benzaldehyde, which was used to synthesize azetidinones (5a–o), (6a–o), and (7a–o). The
structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H NMR, and
13C NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of
the monosubstituted and disubstituted chloro groups are more effective to both bacterial and fungal species in
comparison with the standard drugs.
J. Heterocyclic Chem., 51, 775 (2014).
INTRODUCTION
from 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde and
studied their antimicrobial activity.
Schiff bases are typically formed by the condensation of
a primary amine and aldehyde, which are important inter-
mediates for the synthesis of various bioactive compounds.
They are reported to show a variety of biological activities
including antimicrobial [1–5], antitubercular [6–8], antioxi-
dant, and antiproliferative activities [9]. The b-lactum (2-
azetidinone) skeleton is the key structural unit in penicillins
(e.g., amoxicillin (AMOX), ampicillin (AMP), penicillin G
(PEN G), oxacillin (OXA), and cloxacillin (CLOX)), and
cephalosporins (e.g., cephapirin (CEP)) for antimicrobial
agents. In penicillins and cephalosporins, b-lactam ring
is responsible for the antibacterial activity; besides this, 2-
azetidinone-containing compounds were reported for anti-
microbial [10–15], anti-inflammatory [16–19], analgesic,
CNS depressant, and muscle relaxant activities [19].
Pyridine derivatives also exhibit various biological activities
such as anticancer [20,21], anticonvulsant [22], antiproli-
ferative [23], and also used as g-secretase modulators [24],
JAK2 kinase inhibitors [25], cyclooxygenase-2 (COX-2)
inhibitors [26], and so forth.
RESULT AND DISCUSSION
Chemistry.
The synthesis of Schiff bases and
azetidinones was performed in different synthetic steps as
shown in Scheme 1. Schiff bases 4a–o were synthesized by
condensing 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde
with appropriate aromatic amine in absolute alcohol and
2–3 drops of glacial acetic acid at refluxed temperature.
Azetidinones 5a–o and 6a–o were synthesized from
appropriate Schiff base with bromo acetyl bromide and
chloro acetyl chloride respectively in 1,4-dioxane solvent
and triethyl amine as catalyst; 7a–o were synthesized from
appropriate Schiff base and phenoxy acetic acid in the
presence of thionyl chloride. The purity of the compounds
was checked by TLC and elemental analysis. Spectral data
(IR, H NMR, and 13C NMR) of all the compounds were
in full agreement with the proposed structures.
1
The synthesis of 4a–o and 5a–o was confirmed by the IR
and NMR spectra. The band of –CH═N observed at
1627 cmÀ1 showed the confirmation of Schiff base. Asym-
metric and symmetric band of C–O–C ether linkage was
observed at 1227 and 1046 cmÀ1, respectively. A singlet at
d 8.25 attributed to the –CH═N protons; d 161.4 ppm was
In view of future scope and better enhancement of such
active molecule for new biodynamic fascinating scaffolds,
still modifications are possible to study the different
activities; hence, we have synthesized new 2-azetidinones
© 2013 HeteroCorporation

776
N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
Scheme 1. Synthesis of 4a–o.
R:-
4-F
3,4-F
2-Cl
2-F
3-Cl
3,5-F
4-Cl
2-Br, 4-F
3-Cl, 4-CH3
2,3-Cl
4-CH3
3,4-Cl
2,5-Cl
3,5-Cl
attributed to the –CH═N confirmed by 13C NMR. In 5a–o,
the absence of –CH═N band at 1627 cmÀ1 and presence of
1725 cmÀ1 of –C═O (b-lactam ring) confirmed the conver-
sion of Schiff base in to azetidinones by IR, the signal
appeared at d 5.40 and d 5.15 for the –CH–Cl and –CH of aze-
(E. coli MTCC 442 and P. aeruginosa MTCC 2488)
bacteria are shown in Table 1, 3, and 5. From the screening
results, most of the compounds possessed very good
activity (MIC, 100–250 mg/mL) against S. aureus; some of
them possessed excellent compared with ampicillin.
1
tidinones, respectively, in H NMR, and –C═O carbon that
Most of the compounds possessed very good activity
(MIC, 100–250 mg/mL) against S. aureus; 4e and 4n con-
taining chloro and dichloro groups showed significant ac-
tivity of 100 mg/mL against E. coli. 4e also showed
excellent activity of 100 mg/mL against P. aeruginosa
comparable with ampicillin. Compounds 4g, 4l, 4m, and
4o displayed very good activity at 100–200 mg/mL indicat-
ing that these compounds are very effective against S. au-
reus. The remaining compounds 4d, 4e, 4h, 4k, and 4n
are also active having promising activity with ampicillin.
All Schiff bases were very poor against S. pyogenus.
Azetidinones (5a–o), 5d, 5e, and 5g displayed MIC of
100 mg/mL against E. coli, which are similar as standard
drug. Compound 5d possessed MIC of 150 mg/mL against
P. aeruginosa, which is nearer to ampicillin. 5b, 5g, 5j,
and 5k displayed MIC in the range of 100–200 mg/mL
against S. aureus, which is better compared with ampicil-
lin. Compound 5a possessed better MIC at 250 mg/mL
against S. aureus, whereas 5j found very active against S.
pyogeneus; 5b and 5i are moderate against the aforemen-
tioned species. The rest of the compounds possessed
moderate to poor activity against all four bacterial species.
Azetidinones (6a–o), 6a possessed MIC of 100 mg/mL
clearly appeared at d 162.5 was also observed in 13C NMR.
For compounds 6a–o, the sharp band of –C═O is observed
at 1730 cmÀ1. In 1H NMR spectra, two signals are observed
at d 5.35 and d 5.20 for the –CH–Br and –CH of azetidinone
ring, respectively, whereas –C═O carbon appeared at d 170.8.
For compounds 7a–o, the disappearance of –CH═N
band at 1627 cmÀ1 and appearance of 1722 cmÀ1 of –
C═O lactam ring gave the confirmation of 2-azetidinone.
A signal at d 5.31 and d 5.29 for the –CH–OPh and –CH
of 2-azetidinone and carbonyl carbon of azetidinone
appeared at d 165.1. The aforementioned spectral data con-
firmed the conversion of Schiff base into 2-azetidinone.
Biological activity.
The minimum inhibitory
concentrations (MICs) of all compounds were carried out
by broth microdilution method as described by Rattan
[29]. All MTCC cultures were collected from the Institute
of Microbial Technology, Chandigarh, India. Antibacterial
and antifungal activity data of compounds 4a–o, 5a–o,
6a–o, and 7a–o are described in Tables 1–6, respectively.
Antibacterial activity. The MICs of 4a–o and 5a–o were
tested in vitro against two Gram-positive (S. aureus MTCC
96 and S. pyogenus MTCC 443) and two Gram-negative
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New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
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Table 1
Table 2
Antibacterial activity of 4a–o and 5a–o.
Antifungal activity of 4a–o and 5a–o.
Minimal bactericidal concentration mg/mL
Minimal fungicidal concentration mg/mL
Gram-negative
Gram-positive
Compounds
C. albicans
A.niger
A. clavatus
4a
4b
4c
4d
500
>1000
>1000
200
>1000
1000
>1000
500
>1000
1000
>1000
500
P.
S.
aureus
S.
Compounds
E. coli
aeruginosa
pyogenus
4a
4b
4c
4d
4e
250
500
1000
200
100
250
250
500
1000
500
250
500
250
100
150
250
500
250
100
100
500
100
500
250
125
500
500
500
500
500
100
500
500
1000
250
100
250
250
500
1000
500
200
250
200
150
200
500
500
500
150
250
500
250
250
500
250
500
250
500
500
250
100
500
1000
1000
250
250
500
200
250
500
500
250
150
100
250
100
250
200
500
200
500
1000
100
500
500
200
200
500
1000
250
250
250
500
1000
1000
250
500
500
250
500
500
500
500
200
250
250
250
250
200
500
200
500
500
250
500
200
100
250
500
500
500
250
100
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
5a
5b
5c
5d
5e
5f
5g
5h
5i
5j
5k
5l
5m
250
500
500
500
500
>1000
500
500
>1000
1000
1000
>1000
1000
500
1000
>1000
1000
>1000
500
1000
>1000
500
1000
250
1000
>1000
>1000
>1000
>1000
500
>1000
>1000
>1000
100
1000
>1000
1000
500
1000
1000
1000
>1000
500
1000
>1000
500
1000
250
1000
500
500
>1000
500
>1000
>1000
500
>1000
1000
500
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
5a
5b
5c
5d
5e
5f
500
500
1000
>1000
500
1000
500
200
500
250
250
200
>1000
>1000
500
500
>1000
250
5g
5h
5i
5j
5k
5l
5n
5o
500
100
500
500
100
100
Nystatin
Greseofulvin
5m
5n
5o
Ampicillin
100
Schiff base, 4a, 4d, 4e, 4f, 4g, 4h, 4k, 4l, and 4m, showed
significant activity of 200–500 mg/mL against C. albicans
and comparable with greseofulvin, whereas the remaining
Schiff bases possessed poor activity against A. niger and
A. clavatus. Azetidinones (5a–o), 5a, 5c, 5d, 5e, 5f, 5g,
5h, 5k, 5l, 5n, and 5o possessed excellent activity of
200–500 mg/mL against C. albicans, which is equipotent
to greseofulvin, whereas the remaining compounds showed
moderate to poor activity against A. niger and A. clavatus.
Azetidinones (6a–o), 6n displayed better activity
of 100 mg/mL against C. albicans, which showed that this
compound is more active when compared with greseofulvin
and similar as nystatin drug. Compounds 6a, 6c, 6d, 6e,
6h, and 6k showed to possess very good activity of
200–500 mg/mL against C. albicans with greseofulvin; the
remaining compounds showed moderate to poor activity
against all four fungal species.
against E. coli, which is equipotent to reference drug.
Compounds 6b, 6c, 6d, and 6j displayed MIC in the range
of 100–200 mg/mL against S. aureus. Compounds 7j and 7i
having chloro and dichloro substituents possessed MIC in
the range of 62.5–100 mg/mL against E. coli. Compound
7i possessed very good MIC of 100 mg/mL against P.
aeruginosa, whereas 7a, 7e, 7f, 7g, 7h, 7i, 7k, and 5l
displayed promising activity of 100–250 mg/mL against S.
aureus. Azetidinones are found to be very poor against S.
pyogeneus; the remaining compounds possessed moderate
to poor activity against all four bacterial species.
Antifungal activity. Minimum inhibition concentrations
(MICs for fungus) of the synthesized compounds are shown
in Tables 2, 4, and 6; three fungal species C. albicans MTCC
227, A. niger MTCC 282, and A. clavatus MTCC 1323
were used and compared with greseofulvin. Most of
the compounds possessed very good antifungal activity
against C. albicans; their MICs were in the range of
100–500 mg/mL.
Azetidinone, 7a, 7h, and 7k, possessed excellent activity
of 200–500 mg/mL against C. albicans, 7j having chloro
group displayed significant activity of 100 mg/mL against
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N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
Table 3
Table 5
Antibacterial activity of 6a–o.
Antibacterial activity of 7a–o.
Minimal bactericidal concentration mg/mL
Minimal bactericidal concentration mg/mL
Gram-negative
Gram-positive
Gram-negative
Gram-positive
E.
P.
S.
S.
E.
P.
S.
S.
Compounds
coli
aeruginosa
aureus
pyogeneus
Compounds
coli
aeruginosa
aureus
pyogenus
6a
6b
6c
6d
6e
6f
6g
6h
6i
6j
6k
6l
6m
6n
6o
100
250
200
250
500
500
250
500
250
150
250
250
500
250
500
100
200
250
250
250
500
500
250
500
250
200
200
250
500
500
500
100
250
150
100
200
250
250
500
1000
500
200
500
500
1000
250
500
250
500
200
200
250
250
250
500
1000
500
500
500
500
1000
500
500
100
7a
7b
7c
7d
7e
7f
7g
7h
7i
7j
7k
7l
7m
7n
7o
150
250
250
250
200
250
200
250
100
62.5
250
250
500
250
200
100
200
250
500
200
200
250
200
500
100
200
250
500
200
250
250
100
200
500
500
500
200
150
100
150
200
500
200
250
500
500
500
250
500
500
1000
500
250
200
250
150
200
500
500
500
500
500
500
100
Ampicillin
Ampicillin
Table 4
Table 6
Antifungal activity of 6a–o.
Antifungal activity of 7a–o.
Minimal fungicidal concentration mg/mL
Minimal fungicidal concentration mg/mL
Compounds
C. albicans
A.niger
A. clavatus
Compounds
C. albicans
A.niger
A. clavatus
6a
6b
6c
6d
6e
6f
6g
6h
500
1000
500
200
250
1000
1000
500
>1000
>1000
500
500
1000
1000
200
500
1000
>1000
200
7a
7b
7c
7d
7e
7f
7g
7h
250
1000
1000
1000
1000
1000
1000
500
200
1000
500
>1000
>1000
1000
500
>1000
>1000
200
200
1000
500
>1000
>1000
1000
500
>1000
>1000
200
500
500
1000
1000
500
>1000
>1000
500
1000
1000
500
>1000
>1000
500
6i
6j
6k
7i
7j
7k
1000
100
200
500
500
6l
6m
6n
6o
1000
1000
100
500
100
>1000
>1000
500
>1000
>1000
1000
500
7l
7m
7n
7o
1000
1000
1000
1000
100
500
500
>1000
>1000
1000
100
>1000
>1000
>1000
100
500
100
100
Nystatin
Greseofulvin
100
100
Nystatin
Greseofulvin
500
500
100
100
C. albicans comparable with nystatin, whereas the remaining
compounds showed poor activities against A. niger and A.
clavatus.
• Structure activity relationship study shows that effect of
substituent group plays an important role in the biological
activity following for Schiff bases; compounds bearing
2,4-Cl found to be very active against bacterial species,
promising towards the C. albicans and poor against the
other fungi compared with the compounds bearing other
substituents such as F or –CH3.
CONCLUSIONS
• All the Schiff bases and azetidinones are excellent
against Gram-positive bacteria S. aureus and very good
against fungal species C. albicans.
• Similar results are observed for azetidinones from struc-
ture activity relationship study such as compound having
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New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
779
(C2–C6), 160.7 (C17); Anal. Calcd for C22H20N2OF2:
72.12, H 5.50, N 7.65; found C 72.13, H 5.51, N 7.62.
C
2-Cl is active against E. coli and C. albicans; another
compound bearing 3,5-Cl group is excellent against all
bacteria.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-4-
chlorobenzenamine (4c). This compound was obtained as off
yellow solid; yield, 80%; mp 113–115ꢀC. Rf: 0.47. IR nmax: 3056
(Ar–H), 2960, 2844 (ÀCH2–), 1626 (ÀCH═N), 1227, 1044
(C–O–C), 745 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.15
(t, 3H, –CH3), 2.54 (q, 2H, –CH2), 3.16 (t, 2H, –CH2), 4.30
(t, 2H, –CH2–O), 7.05–7.87 (m, 8H, Ar–H), 7.35–8.35
(m, 3H, Pyridine–H), 8.28 (s, 1H, –CH═N–); 13C NMR (dc,
CDCl3, 100 MHz): 15.7 (C8), 32.6 (C7), 37.5 (C9), 67.3 (C10),
115.2–155.4 (C11–C16), 123.7–151.3 (C18–C23), 123.2–157.6
(C2–C6), 160.7 (C17); Anal. Calcd for C22H21N2OCl: C 72.42,
EXPERIMENTAL
Laboratory chemicals were supplied by Rankem India Ltd. and
Ficher Scientific Ltd. Melting points were determined by the open
tube capillary method and are uncorrected. The purity of the
compounds was determined by TLC plates (silica gel G) in the
solvent system toluene:ethyl acetate (7.5:2.5). The spots were
observed by exposure to iodine vapors or by UV light. The IR
spectra were obtained on a PerkinElmer 1720 FTIR spectrometer
(KBr pellets). The 1H NMR and 13C NMR spectra were recorded
on a Bruker Avance II 400 spectrometer by using TMS as an
internal standard in CDCl3. Elemental analysis of the newly
synthesized compounds were carried out on Carlo Erba 1108
analyzer.
H 5.80, N 7.68; found C 72.41, H 5.79, N 7.66.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-3,4-
dichlorobenzenamine (4d). This compound was obtained as
off yellow liquid; yield, 78%; mp limpid. Rf: 0.43. IR nmax
:
3057 (Ar–H), 2957, 2845 (ÀCH2–), 1629 (ÀCH═N), 1228,
1046 (C–O–C), 746 (C–Cl); 1H NMR (d CDCl3, 400 MHz):
1.14 (t, 3H, –CH3), 2.56 (q, 2H, –CH2), 3.13 (t, 2H, –CH2),
4.33 (t, 2H, –CH2–O), 7.09–7.86 (m, 7H, Ar–H), 7.33–8.35
(m, 3H, Pyridine–H), 8.25 (s, 1H, –CH═N–); 13C NMR (dc,
CDCl3, 100 MHz): 15.6 (C8), 32.5 (C7), 37.7 (C9), 67.4 (C10),
115.4–155.6 (C11–C16), 121.8–152.6 (C18–C23), 123.4–157.4
(C2–C6), 160.5 (C17); Anal. Calcd for C22H20N2OCl2: C 66.17,
Procedure for the synthesis of 4-[2-(5-ethylpyridin-2-yl)
ethoxy]benzaldehyde (3).
4-[2-(5-Ethylpyridin-2-yl)ethoxy]
benzaldehyde (3) was synthesized by the method described in
the literature[27,28].
General preparation of the compounds (4a–o). A mixture
of 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde (0.01 mol) and
aromatic amine (0.01 mol) was taken in absoluted ethanol, and
few drops of glacial acetic acid were added. Then, the mixture
was refluxed for 6–8 h on water bath. The excess solvent was
distilled off, and then the remaining residue poured in to ice
cold water. The separated solid was filtered, washed, and
H 5.05, N 7.02; found C 66.15, H 5.04, N 7.00.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2,4-
dichlorobenzenamine (4e). This compound was obtained as
off yellow liquid; yield, 75%; mp limpid. Rf: 0.50. IR nmax
:
3056 (Ar–H), 2957, 2847 (ÀCH2–), 1624 (ÀCH═N), 1227,
1043 (C–O–C), 745 (C–Cl); 1H NMR (d CDCl3, 400 MHz):
1.13 (t, 3H, –CH3), 2.54 (q, 2H, –CH2), 3.15 (t, 2H, –CH2),
4.35 (t, 2H, –CH2–O), 6.70–7.88 (m, 7H, Ar–H), 7.34–8.35
(m, 3H, Pyridine–H), 8.26 (s, 1H, –CH═N–); 13C NMR (dc,
CDCl3, 100 MHz): 15.4 (C8), 32.6 (C7), 37.5 (C9), 67.5 (C10),
115.3–155.7 (C11–C16), 125.1–141.3 (C18–C23), 123.5–157.3
(C2–C6), 160.4 (C17); Anal. Calcd for C22H20N2OCl2: C 66.17,
recrystalized from ethanol (Fig. 1).
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-4-
fluorobenzenamine (4a). This compound was obtained as off
white solid; yield, 70%; mp 85–87ꢀC. Rf: 0.45. IR nmax: 3055
(Ar–H), 2956, 2844 (ÀCH2–), 1628 (ÀCH═N), 1227, 1045
(C–O–C), 972 (C–F); 1H NMR (d CDCl3, 400 MHz): 1.12
(t, 3H, –CH3), 2.50 (q, 2H, –CH2), 3.17 (t, 2H, –CH2), 4.32
(t, 2H, –CH2–O), 7.00–7.87 (m, 8H, Ar–H), 7.34–8.34 (m, 3H,
Pyridine–H), 8.27 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.4 (C8), 32.5 (C7), 37.5 (C9), 67.6 (C10),
115.2–155.4 (C11–C16), 116.5–161.4 (C18–C23), 123.3–157.3
H 5.05, N 7.02; found C 66.16, H 5.06, N 7.01.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-3,4-
difluorobenzenamine (4f).
This compound was obtained as
yellow solid; yield, 68%; mp 120–122ꢀC. Rf: 0.51. IR nmax
:
(C2–C6), 160.6 (C17); Anal. Calcd for C22H21N2OF:
C
3059 (Ar–H), 2954, 2845 (ÀCH2–), 1626 (ÀCH═N), 1226,
75.84, H 6.08, N 8.04; found C 75.82, H 6.09, N 8.05.
1
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-3,5-
difluorobenzenamine (4b). This compound was obtained as
1045 (C–O–C), 973 (C–F); H NMR (d CDCl3, 400 MHz): 1.16
(t, 3H, –CH3), 2.53 (q, 2H, –CH2), 3.13 (t, 2H, –CH2), 4.36
(t, 2H, –CH2–O), 6.89–7.85 (m, 7H, Ar–H), 7.34–8.37 (m, 3H,
Pyridine–H), 8.25 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.7 (C8), 32.4 (C7), 37.6 (C9), 67.6 (C10),
115.0–155.5 (C11–C16), 111.2–150.3 (C18–C23), 123.1–157.4
off white solid; yield, 72%; mp 100–103ꢀC. Rf: 0.43. IR nmax
:
3058 (Ar–H), 2958, 2845 (ÀCH2–), 1627 (ÀCH═N), 1228,
1
1046 (C–O–C), 974 (C–F); H NMR (d CDCl3, 400 MHz): 1.13
(t, 3H, –CH3), 2.52 (q, 2H, –CH2), 3.15 (t, 2H, –CH2), 4.33 (t,
2H, –CH2–O), 6.72–7.85 (m, 7H, Ar–H), 7.34–8.36 (m, 3H,
Pyridine–H), 8.26 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.7 (C8), 32.6 (C7), 37.5 (C9), 67.3 (C10),
115.2–155.4 (C11–C16), 123.7–151.3 (C18–C23), 123.2–157.6
(C2–C6), 160.8 (C17); Anal. Calcd for C22H20N2OF2:
C
72.12, H 5.50, N 7.65; found C 72.11, H 5.51, N 7.64.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene2-bromo)-
4-fluorobenzenamine (4g). This compound was obtained as
off brown liquid; yield, 59%; mp limpid. Rf: 0.46. IR nmax: 3056
(Ar–H), 2955, 2844 (ÀCH2–), 1627 (ÀCH═N), 1225, 1046
1
(C–O–C), 972 (C–F), 857 (C–Br); H NMR (d CDCl3, 400 MHz):
1.14 (t, 3H, –CH3), 2.57 (q, 2H, –CH2), 3.16 (t, 2H, –CH2), 4.34
(t, 2H, –CH2–O), 6.89–7.86 (m, 7H, Ar–H), 7.30–8.38 (m, 3H,
Pyridine–H), 8.27 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.8 (C8), 32.5 (C7), 37.4 (C9), 67.7 (C10), 115.2–155.3
(C11–C16), 112.6–163.5 (C18–C23), 123.2–157.6 (C2–C6), 160.7
(C17); Anal. Calcd for C22H20N2OFBr: C 61.84, H 4.72, N 6.56;
found C 61.80, H 4.71, N 6.53.
Figure 1. Schiff base 4a–o.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

780
N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)3-chloro-
4-methyl benzenamine (4h). This compound was obtained as
off brown solid; yield, 62%; mp 135–137ꢀC. Rf: 0.48. IR nmax
brown liquid; yield, 71%; mp limpid. Rf: 0.43. IR nmax: 3056
(Ar–H), 2957, 2845 (ÀCH2–), 1627 (ÀCH═N), 1227, 1046
(C–O–C), 746 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.20
(t, 3H, –CH3), 2.58 (q, 2H, –CH2), 3.15 (t, 2H, –CH2), 4.35
(t, 2H, –CH2–O), 7.07–7.83 (m, 7H, Ar–H), 7.32–8.36 (m, 3H,
Pyridine–H), 8.28 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.4 (C8), 32.4 (C7), 37.7 (C9), 67.5 (C10),
115.2–155.4 (C11–C16), 121.8–144.6 (C18–C23), 123.2–157.4
(C2–C6), 160.5 (C17); Anal. Calcd for C22H20N2OCl2: C
:
3058 (Ar–H), 2958, 2845 (ÀCH2–), 1628 (ÀCH═N), 1228, 1046
(C–O–C), 744 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.18
(t, 3H, –CH3), 2.35 (s, 3H, –CH3), 2.58 (q, 2H, –CH2), 3.15
(t, 2H, –CH2), 4.33 (t, 2H, –CH2–O), 7.00–7.82 (m, 7H, Ar–H),
7.35–8.36 (m, 3H, Pyridine–H), 8.24 (s, 1H, –CH═N–); 13C NMR
(dc, CDCl3, 100 MHz): 15.6 (C8), 20.1 (C24), 32.6 (C7), 37.6 (C9),
67.5 (C10), 115.8–155.4 (C11–C16), 120.0–151.5 (C18–C23),
123.4–157.8 (C2–C6), 160.3 (C17); Anal. Calcd for C23H23N2OCl:
C 72.91, H 6.12, N 7.39; found C 72.90, H 6.10, N 7.36.
66.17, H 5.05, N 7.02; found C 66.16, H 5.04, N 7.03.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-3-
chlorobenzenamine (4n).
This compound was obtained as
brown liquid; yield, 76%; mp limpid. Rf: 0.51. IR nmax: 3056
(Ar–H), 2956, 2846 (ÀCH2–), 1626 (ÀCH═N), 1226, 1046
(C–O–C), 744 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.24
(t, 3H, –CH3), 2.52 (q, 2H, –CH2), 3.15 (t, 2H, –CH2), 4.32
(t, 2H, –CH2–O), 7.03–8.23 (m, 8H, Ar–H), 7.33–8.34 (m, 3H,
Pyridine–H), 8.27 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.7 (C8), 32.5 (C7), 37.6 (C9), 67.6 (C10),
115.3–155.7 (C11–C16), 120.4–154.6 (C18–C23), 123.5–157.5
(C2–C6), 160.6 (C17); Anal. Calcd for C22H21N2OCl: C 72.42, H
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-3,5-
dichlorobenzenamine (4i).
This compound was obtained as
off yellow solid; yield, 77%; mp 110–112ꢀC. Rf: 0.43. IR nmax
:
3056 (Ar–H), 2956, 2843 (ÀCH2–), 1627 (ÀCH═N), 1224,
1045 (C–O–C), 746 (C–Cl); 1H NMR (d CDCl3, 400 MHz):
1.17 (t, 3H, –CH3), 2.58 (q, 2H, –CH2), 3.15 (t, 2H, –CH2),
4.33 (t, 2H, –CH2–O), 7.05–7.84 (m, 7H, Ar–H), 7.35–8.36 (m,
3H, Pyridine–H), 8.24 (s, 1H, –CH═N–); 13C NMR (dc,
CDCl3, 100 MHz): 15.6 (C8), 32.6 (C7), 37.6 (C9), 67.5 (C10),
115.8–155.4 (C11–C16), 120.5–156.1 (C18–C23), 123.4–157.6
(C2–C6), 160.5 (C17); Anal. Calcd for C22H20N2OCl2: C 66.17,
H 5.05, N 7.02; found C 66.18, H 5.04, N 7.04.
5.80, N 7.68; found C 72.43, H 5.82, N 7.69.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-4-
methylbenzenamine (4o). This compound was obtained as off
white solid; yield, 70%; mp 80–83ꢀC. Rf: 0.52. IR nmax: 3056
(Ar–H), 2957, 2845 (ÀCH2–), 1627 (ÀCH═N), 1227, 1046
(C–O–C); 1H NMR (d CDCl3, 400 MHz): 1.13 (t, 3H, –CH3),
2.24 (s, 3H, –CH3), 2.52 (q, 2H, –CH2), 3.17 (t, 2H, –CH2),
4.29 (t, 2H, –CH2–O), 6.85–7.69 (m, 8H, Ar–H), 7.34–8.30 (m,
3H, Pyridine–H), 8.25 (s, 1H, –CH═N–); 13C NMR (dc,
CDCl3, 100 MHz): 15.4 (C8), 25.7 (C24), 32.4 (C7), 37.4 (C9),
67.4 (C10), 115.2–155.3 (C11–C16), 120.8–148.9 (C18–C23),
123.4–158.9 (C2–C6), 161.4 (C17); Anal. Calcd for C23H24N2O:
C 80.20, H 7.02, N 8.13; found C 80.22, H 7.03, N 8.11.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2-
chlorobenzenamine (4j).
This compound was obtained as
brown liquid; yield, 78%; mp limpid. Rf: 0.44. IR nmax: 3057
(Ar–H), 2957, 2846 (ÀCH2–), 1627 (ÀCH═N), 1229, 1047
(C–O–C), 745 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.15
(t, 3H, –CH3), 2.56 (q, 2H, –CH2), 3.14 (t, 2H, –CH2), 4.34
(t, 2H, –CH2–O), 7.08–7.82 (m, 8H, Ar–H), 7.34–8.37 (m, 3H,
Pyridine–H), 8.22 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.4 (C8),), 32.5 (C7), 37.7 (C9), 67.6 (C10),
115.5–155.3 (C11–C16), 123.–143.4 (C18–C23), 123.5–157.3
(C2–C6), 160.2 (C17); Anal. Calcd for C22H21N2OCl: C 72.42,
General preparation of the compounds (5a–o).
To a
stirred solution 4a–o (0.05 mol) in 1,4-dioxane (100 mL), bromo
acetyl bromide (0.05 mol) was added dropwise at 0–5ꢀC
temperature in presence of triethyl amine. The reaction mixture
was stirred for about 6–10 h, and the precipitated was filtered off.
The filtrate was refluxed for 4–6 h and completion of reaction
monitored by TLC. (toluene:ethylacetate, 7:3) and the separated
H 5.80, N 7.68; found C 72.44, H 5.81, N 7.67.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2-
fluorobenzenamine (4k).
This compound was obtained as
brown liquid; yield, 69%; mp limpid. Rf: 0.47. IR nmax: 3056
(Ar–H), 2958, 2845 (ÀCH2–), 1627 (ÀCH═N), 1227, 1048
(C–O–C), 975 (C–F); 1H NMR (d CDCl3, 400 MHz): 1.16
(t, 3H, –CH3), 2.57 (q, 2H, –CH2), 3.16 (t, 2H, –CH2), 4.36
(t, 2H, –CH2–O), 7.00–7.85 (m, 8H, Ar–H), 7.35–8.38 (m, 3H,
Pyridine–H), 8.24 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.1 (C8), 32.5 (C7), 37.2 (C9), 67.5 (C10),
115.4–155.4 (C11–C16), 116.8–153.2 (C18–C23), 123.4–157.4
solid was recrystallized from alcohol (Scheme-2) (Figure-2).
3-Bromo-1-(4-fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (5a).
This compound was
obtained as brown liquid; yield, 55%; mp semi-solid. Rf: 0.78.
IR nmax: 3050 (Ar–H), 2947, 2845 (ÀCH2–), 1730 (ÀC═O of
b-lactam ring), 1222, 1028 (C–O–C), 855 (C–Br), 974 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.27 (t, 3H, –CH3), 2.87 (q, 2H,
–CH2), 3.66 (t, 2H, –CH2), 4.58 (t, 2H, –CH2–O), 5.25 (d, 1H,
–CH–Br), 6.70–7.22 (m, 8H, Ar–H), 7.32–8.62 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.1 (C8), 32.5
(C7), 37.2 (C9), 50.2 (C18), 64.3 (C17), 67.5 (C10), 114.9–155.2
(C11–C16), 122.3–157.3 (C2–C6), 115.7–158.2 (C20–C25), 170.9
(C19). Anal. Calcd for C24H22N2O2FBr: C 61.42, H 4.72, N
(C2–C6), 160.3 (C17); Anal. Calcd for C22H21N2OF:
75.84, H 6.08, N 8.04; found C 75.82, H 6.06, N 8.03.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2,5-
C
dichlorobenzenamine (4l).
This compound was obtained as
brown liquid; yield, 75%; mp limpid. Rf: 0.42. IR nmax: 3059
(Ar–H), 2955, 2845 (ÀCH2–), 1629 (ÀCH═N), 1225, 1049
(C–O–C), 746 (C–Cl); 1H NMR (d CDCl3, 400 MHz): 1.19
(t, 3H, –CH3), 2.53 (q, 2H, –CH2), 3.17 (t, 2H, –CH2), 4.37
(t, 2H, –CH2–O), 7.06–7.88 (m, 7H, Ar–H), 7.33–8.36 (m, 3H,
Pyridine–H), 8.26 (s, 1H, –CH═N–); 13C NMR (dc, CDCl3,
100 MHz): 15.3 (C8), 32.6 (C7), 37.4 (C9), 67.6 (C10),
115.5–155.6 (C11–C16), 124.0–144.6 (C18–C23), 123.5–157.7
(C2–C6), 160.7 (C17); Anal. Calcd for C22H20N2OCl2: C
5.97; found C 61.41, H 4.71, N 5.95.
3-Bromo-1-(3,5-difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5b).
This compound was
obtained as brown solid; yield, 58%; mp 134–136ꢀC. Rf: 0.72.
IR nmax: 3047 (Ar–H), 2944, 2846 (ÀCH2–), 1728 (ÀC═O of
b-lactam ring), 1221, 1029 (C–O–C), 854 (C–Br), 973 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.26 (t, 3H, –CH3), 2.86 (q, 2H,
–CH2), 3.65 (t, 2H, –CH2), 4.56 (t, 2H, –CH2–O), 5.23 (d, 1H,
66.17, H 5.05, N 7.02; found C 66.15, H 5.03, N 7.04.
N-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzylidene)-2,3-
dichlorobenzenamine (4m). This compound was obtained as
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2014
New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
781
Scheme 2. Synthesis of 5a–o, 6a–o, and 7a–o.
R:-
4-F
3,4-F
2-Cl
2-F
3-Cl
3,5-F
4-Cl
2-Br, 4-F
3-Cl, 4-CH3
2,3-Cl
4-CH3
3,4-Cl
2,5-Cl
3,5-Cl
(C19). Anal. Calcd for C24H22N2O2ClBr: C 59.34, H 4.56, N
5.77; found C 59.35, H 4.54, N 5.76.
3-Bromo-1-(3,4-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5d).
This compound was
obtained as brown solid; yield, 65%; mp 140–142ꢀC. Rf: 0.78.
IR nmax: 3045 (Ar–H), 2943, 2842 (ÀCH2–), 1725 (ÀC═O of
b-lactam ring), 1225, 1025 (C–O–C), 746 (C–Cl), 853 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.27 (t, 3H, –CH3), 2.84 (q, 2H,
–CH2), 3.65 (t, 2H, –CH2), 4.56 (t, 2H, –CH2–O), 5.27 (d, 1H,
–CH–Br), 6.71–7.25 (m, 7H, Ar–H), 7.36–8.67 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.5 (C8), 32.4
(C7), 37.2 (C9), 50.4 (C18), 64.3 (C17), 67.6 (C10), 114.4–155.3
(C11–C16), 122.4–157.6 (C2–C6), 121.4–141.3 (C20–C25), 170.5
(C19). Anal. Calcd for C24H21N2O2Cl2Br: C 55.41, H 4.07, N
Figure 2. Azetidinone 5a–o.
–CH–Br), 6.55–7.23 (m, 7H, Ar–H), 7.34–8.64 (m, 3H, Pyridine–H);
13C NMR (dc, CDCl3, 100 MHz): 15.2 (C8), 32.6 (C7), 37.4 (C9),
50.4 (C18), 64.5 (C17), 67.2 (C10), 114.5–155.4 (C11–C16),
122.4–157.5 (C2–C6), 100.2–164.7 (C20–C25), 170.8 (C19).
Anal. Calcd for C24H21N2O2F2Br: C 59.15, H 4.34, N 5.75;
5.38; found C 55.42, H 4.06, N 5.39.
3-Bromo-1-(2,4-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5e).
This compound was
found C 59.16, H 4.32, N, 5.76.
3-Bromo-1-(4-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
obtained as brown solid; yield, 64%; mp 137–138ꢀC. Rf: 0.74.
IR nmax: 3047 (Ar–H), 2947, 2846 (ÀCH2–), 1726 (ÀC═O of
b-lactam ring), 1220, 1029 (C–O–C), 746 (C–Cl), 854 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.26 (t, 3H, –CH3), 2.86 (q, 2H,
–CH2), 3.63 (t, 2H, –CH2), 4.56 (t, 2H, –CH2–O), 5.37 (d, 1H,
–CH–Br), 5.26 (s, 1H, –CH–Br), 7.35–8.65 (m, 3H, Pyridine–H);
13C NMR (dc, CDCl3, 100 MHz): 15.2 (C8), 32.5 (C7), 37.3
(C9), 50.8 (C18), 64.4 (C17), 67.8 (C10), 114.6–155.7 (C11–C16),
122.3–157.5 (C2–C6), 124.4–138.4 (C20–C25), 170.6 (C19).
Anal. Calcd for C24H21N2O2Cl2Br: C 55.41, H 4.07, N,5.38;
found C 55.40, H 4.05, N, 5.37.
ethoxy)phenyl)azetidin-2-one (5c).
This compound was
obtained as brown solid; yield, 62%; mp 155–156ꢀC. Rf: 0.75.
IR nmax: 3046 (Ar–H), 2946, 2842 (ÀCH2–), 1729 (ÀC═O of
b-lactam ring), 1220, 1026 (C–O–C), 744 (C–Cl), 855 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.25 (t, 3H, –CH3), 2.85 (q, 2H,
–CH2), 3.63 (t, 2H, –CH2), 4.54 (t, 2H, –CH2–O), 5.29 (d, 1H,
–CH–Br), 6.72–7.45 (m, 8H, Ar–H), 7.34–8.66 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.4 (C8), 32.5
(C7), 37.3 (C9), 50.2 (C18), 64.4 (C17), 67.4 (C10), 114.3–155.5
(C11–C16), 122.3–157.4 (C2–C6), 123.0–139.5 (C20–C25), 170.7
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

782
N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
3-Bromo-1-(3,4-difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5f). This compound was
(C7), 37.5 (C9), 50.3 (C18), 64.4 (C17), 67.8 (C10), 114.2–155.0
(C11–C16), 122.3–157.3 (C2–C6), 123.0–140.5 (C20–C25), 170.6
(C19). Anal. Calcd for C24H22N2O2ClBr: C 59.34, H 4.56, N
obtained as brown liquid; yield, 57%; mp semi-solid. Rf: 0.72.
IR nmax: 3051 (Ar–H), 2950, 2843 (ÀCH2–), 1729 (ÀC═O of
b-lactam ring), 1224, 1025 (C–O–C), 852 (C–Br), 974 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.28 (t, 3H, –CH3), 2.87 (q, 2H,
–CH2), 3.66 (t, 2H, –CH2), 4.53 (t, 2H, –CH2–O), 5.21 (d, 1H,
–CH–Br), 6.72–7.22 (m, 7H, Ar–H), 7.30–8.67 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.4 (C8), 32.1
(C7), 37.6 (C9), 50.4 (C18), 64.5 (C17), 67.9 (C10), 114.3–155.4
(C11–C16), 122.5–157.4 (C2–C6), 111.6–149.6 (C20–C25), 170.5
(C19). Anal. Calcd for C24H21N2O2F2Br: C 59.15, H 4.34, N
5.77; found C 59.32, H 4.55, N 5.75.
3-Bromo-1-(3-fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (5k).
This compound was
obtained as brown liquid; yield, 55%; mp semi-solid. Rf: 0.78.
IR nmax: 3048 (Ar–H), 2946, 2846 (ÀCH2–), 1726 (ÀC═O of
b-lactam ring), 1228, 1028 (C–O–C), 856 (C–Br), 973 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.25 (t, 3H, –CH3), 2.84 (q, 2H,
–CH2), 3.64 (t, 2H, –CH2), 4.56 (t, 2H, –CH2–O), 5.28 (d, 1H,
–CH–Br), 6.73–7.25 (m, 8H, Ar–H), 7.35–8.67 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.6 (C8), 32.1
(C7), 37.6 (C9), 50.2 (C18), 64.3 (C17), 67.2 (C10), 114.5–155.2
(C11–C16), 122.4–157.7 (C2–C6), 115.7–163.0 (C20–C25), 170.2
(C19). Anal. Calcd for C24H22N2O2FBr: C 61.42, H 4.72, N
5.75; found C 59.14, H 4.33, N, 5.76.
3-Bromo-1-(2-bromo-4-fluorophenyl)-4-(4-(2-(5-ethylpyridin-
2-yl)ethoxy)phenyl) azetidin-2-one (5g).
This compound was
obtained as off brown solid; yield, 50%; mp 178–180ꢀC. Rf: 0.77.
IR nmax: 3048 (Ar–H), 2948, 2842 (ÀCH2–), 1725 (ÀC═O
of b-lactam ring), 1223, 1027 (C–O–C), 854 (C–Br), 972
5.97; found C 61.40, H 4.70, N, 5.96.
3-Bromo-1-(2,5-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
1
ethoxy)phenyl) azetidin-2-one (5l).
This compound was
(C–F); H NMR (d CDCl3, 400 MHz): 1.26 (t, 3H, –CH3), 2.58
obtained as brown liquid; yield, 55%; mp semi-solid. Rf: 0.76.
IR nmax: 3045 (Ar–H), 2945, 2845 (ÀCH2–), 1725 (ÀC═O of
b-lactam ring), 1220, 1023 (C–O–C), 745 (C–Cl), 854 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.27 (t, 3H, –CH3), 2.85 (q, 2H,
–CH2), 3.63 (t, 2H, –CH2), 4.57 (t, 2H, –CH2–O), 5.30 (d, 1H,
–CH–Br), 6.72–7.55 (m, 7H, Ar–H), 7.37–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.4 (C8), 32.3
(C7), 37.5 (C9), 50.7 (C18), 64.1 (C17), 67.9 (C10), 114.6–155.4
(C11–C16), 122.3–157.6 (C2–C6), 123.5–141.6 (C20–C25), 170.4
(C19). Anal. Calcd for C24H21N2O2Cl2Br: C 55.41, H 4.07, N
(q, 2H, –CH2), 3.65 (t, 2H, –CH2), 4.54 (t, 2H, –CH2–O), 5.23 (d,
1H, –CH–Br), 6.72–7.23 (m, 7H, Ar–H), 7.32–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100MHz): 15.7 (C8), 32.2
(C7), 37.5 (C9), 50.3 (C18), 64.3 (C17), 67.5 (C10), 114.2–155.6
(C11–C16), 122.4–157.6 (C2–C6), 114.5–160.6 (C20–C25), 170.4
(C19). Anal. Calcd for C24H21N2O2FBr2: C 52.58, H 3.86, N
5.11; found C 52.57, H 3.84, N 5.10.
3-Bromo-1-(3-chloro-4-methylphenyl)-4-(4-(2-(5-ethylpyridin-
2-yl)ethoxy)phenyl) azetidin-2-one (5h). This compound was
obtained as yellow solid; yield, 52%, mp 125–127ꢀC. Rf: 0.78. IR
n
max: 3052 (Ar–H), 2946, 2843 (ÀCH2–), 1726 (ÀC═O of b-
5.38; found C 55.43, H 4.06, N 5.39.
3-Bromo-1-(2,3-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
lactam ring), 1226, 1027 (C–O–C), 745 (C–Cl), 854 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.29 (t, 3H, –CH3), 2.32 (s,
3H, –CH3), 2.85 (q, 2H, –CH2), 3.64 (t, 2H, –CH2), 4.56 (t,
2H, –CH2–O), 5.25 (d, 1H, –CH–Br), 6.72–7.22 (m, 7H, Ar–H),
7.34–8.67 (m, 3H, Pyridine–H); 13C NMR (dc, CDCl3,
100 MHz): 15.3 (C8), 20.5 (C26), 32.4 (C7), 37.1 (C9),
50.3 (C18), 64.7 (C17), 67.8 (C10), 114.0–155.2 (C11–C16),
122.5–157.1 (C2–C6), 119.5–140.1 (C20–C25), 170.8 (C19).
Anal. Calcd for C25H24N2O2ClBr: C 60.07, H 4.84, N 5.60;
ethoxy)phenyl) azetidin-2-one (5m).
This compound was
obtained as pale yellow solid; yield, 58%; mp 134–136ꢀC. Rf:
0.75. IR nmax: 3047 (Ar–H), 2946, 2848 (ÀCH2–), 1728
(ÀC═O of b-lactam ring), 1225, 1027 (C–O–C), 746 (C–Cl),
1
854 (C–Br); H NMR (d CDCl3, 400 MHz): 1.25 (t, 3H, –CH3),
2.87 (q, 2H, –CH2), 3.61 (t, 2H, –CH2), 4.52 (t, 2H, –CH2–O),
5.32 (d, 1H, –CH–Br), 6.72–7.76 (m, 7H, Ar–H), 7.35–8.69 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.7 (C8),
32.3 (C7), 37.2 (C9), 50.5 (C18), 64.3 (C17), 67.4 (C10),
114.7–155.6 (C11–C16), 122.5–157.5 (C2–C6), 121.2–141.6
(C20–C25), 170.3 (C19). Anal. Calcd for C24H21N2O2Cl2Br:
found C 60.05, H 4.83, N 5.61.
3-Bromo-1-(3,5-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5i).
This compound was
obtained as brown liquid; yield, 61%; mp semi-solid. Rf: 0.71.
IR nmax: 3049 (Ar–H), 2949, 2846 (ÀCH2–), 1728 (ÀC═O of
b-lactam ring), 1223, 1025 (C–O–C), 745 (C–Cl). 855 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.26 (t, 3H, –CH3), 2.86 (q, 2H,
–CH2), 3.65 (t, 2H, –CH2), 4.57 (t, 2H, –CH2–O), 5.27 (d, 1H,
–CH–Br), 6.72–7.25 (m, 7H, Ar–H), 7.35–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.0 (C8), 32.4
(C7), 37.2 (C9), 50.6 (C18), 64.2 (C17), 67.3 (C10), 114.4–155.5
(C11–C16), 122.1–157.4 (C2–C6), 120.5–144.6 (C20–C25), 170.7
(C19). Anal. Calcd for C24H21N2O2Cl2Br: C 55.41, H 4.07, N
C 55.41, H 4.07, N 5.38; found C 55.40, H 4.05, N 5.37.
3-Bromo-1-(3-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (5n).
This compound was
obtained as brown liquid; yield, 64%; mp semi-solid. Rf: 0.77.
IR nmax: 3047 (Ar–H), 2946, 2848 (ÀCH2–), 1728 (ÀC═O of
b-lactam ring), 1225, 1027 (C–O–C), 746 (C–Cl), 854 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.25 (t, 3H, –CH3), 2.87 (q, 2H,
–CH2), 3.61 (t, 2H, –CH2), 4.52 (t, 2H, –CH2–O), 5.31 (d, 1H,
–CH–Br), 6.72–7.76 (m, 7H, Ar–H), 7.35–8.69 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.2 (C8), 32.4
(C7), 37.4 (C9), 50.2 (C18), 64.5 (C17), 67.3 (C10), 114.5–155.3
(C11–C16), 122.2–157.2 (C2–C6), 119.7–143.5 (C20–C25), 170.6
(C19) Anal. Calcd for C24H22N2O2ClBr: C 59.34, H 4.56, N
5.38; found C 55.40, H 4.06, N 5.36.
3-Bromo-1-(2-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (5j).
This compound was
obtained as brown liquid; yield, 63%; mp semi-solid. Rf: 0.73.
IR nmax: 3047 (Ar–H), 2947, 2847 (ÀCH2–), 1727 (ÀC═O of
b-lactam ring), 1222, 1027 (C–O–C), 744 (C–Cl), 854 (C–Br);
1H NMR (d CDCl3, 400 MHz): 1.26 (t, 3H, –CH3), 2.86 (q, 2H,
–CH2), 3.65 (t, 2H, –CH2), 4.57 (t, 2H, –CH2–O), 5.23 (d, 1H,
–CH–Br), 6.74–7.51 (m, 8H, Ar–H), 7.35–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.5 (C8), 32.2
5.77; found C 59.33, H 4.54, N 5.75.
3-Bromo-1-(4-methylphenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (5o).
This compound was
obtained as pale brown solid; yield, 62%; mp 110–112ꢀC, Rf:
0.75. IR nmax: 3047 (Ar–H), 2946, 2842 (ÀCH2–), 1720 (ÀC═O
of b-lactam ring), 1220, 1027 (C–O–C), 836 (C–Br); 1H NMR (d
CDCl3, 400MHz): 1.29 (t, 3H, –CH3), 2.35 (s, 3H, –CH3), 2.83
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2014
New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
783
(q, 2H, –CH2), 3.69 (t, 2H, –CH2), 4.55 (t, 2H, –CH2–O), 5.20
(d, 1H, –CH–Br), 7.00–7.81 (m, 8H, Ar–H), 7.31–8.61 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 15.3 (C8), 25.7
(C26), 32.0 (C7), 37.2 (C9), 50.1 (C18), 64.2 (C17), 67.4 (C10),
114.8–155.2 (C11–C16), 122.3–159.5 (C2–C6), 122.2–137.2
(C20–C25), 170.2 (C19). Anal. Calcd for C25H25N2O2Br: C
64.52, H 5.41, N 6.02; found C 64.51, H 5.40, N 6.04.
General preparation of the compounds (6a–o). To a stirred
solution 4a–o (0.05 mol) in 1,4-dioxane (100 mL), chloro acetyl
chloride (0.05 mol) was added dropwise at 0–5ꢀC temperature in
presence of triethyl amine. The reaction mixture was stirred for
about 6–12h, and the precipitated amine hydrochloride was
filtered off. The filtrate was refluxed for 10–12 h and completion
of reaction monitored by TLC. (toluene:ethylacetate, 7:3) and the
(C2–C6), 123.1–139.8 (C20–C25), 163.0 (C19). Anal. Calcd for
C24H21N2O2F2Cl: C 65.09, H 4.78, N 6.33; found C 65.11, H
4.79, N 6.34.
3-Chloro-1-(3,4-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (6d).
This compound was
obtained as off brown solid; yield, 58%; mp 151–153ꢀC. Rf:
0.75. IR nmax: 3053 (Ar–H), 2942, 2846 (ÀCH2–), 1723
(ÀC═O of b-lactam ring), 1226, 1025 (C–O–C), 746 (C–Cl);
1H NMR (d CDCl3, 400 MHz): 1.17 (t, 3H, –CH3), 2.55 (q, 2H,
–CH2), 3.20 (t, 2H, –CH2), 4.21 (t, 2H, –CH2–O), 5.10 (d, 1H,
–CH–Cl), 6.72–7.26 (m, 7H, Ar–H), 7.32–8.61 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.3 (C8), 32.3
(C7), 36.5 (C9), 62.5 (C18), 63.3 (C17), 67.5 (C10), 114.1–155.0
(C11–C16), 122.8–157.2 (C2–C6), 121.1–141.5 (C20–C25), 163.6
(C19). Anal. Calcd for C24H21N2O2Cl3: C 60.58, H 4.45, N
separated solid was recrystallized from alcohol (Scheme 2, Fig. 3).
3-Chloro-1-(4-fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
5.89; found C 60.56, H 4.44, N, 5.88.
phenyl)azetidin-2-one (6a). This compound was obtained as dark
brown solid; yield, 58%; mp 115–118ꢀC. Rf: 0.78. IR nmax: 3052
(Ar–H), 2942, 2845 (ÀCH2–), 1725 (ÀC═O of b-lactam ring),
1225, 1026 (C–O–C), 745 (C–Cl), 973 (C–F); 1H NMR (d
CDCl3, 400 MHz): 1.15 (t, 3H, –CH3), 2.54 (q, 2H, –CH2), 3.12
(t, 2H, –CH2), 4.29 (t, 2H, –CH2–O), 5.12 (d, 1H, –CH–Cl),
6.72–7.22 (m, 8H, Ar–H), 7.32–8.62 (m, 3H, Pyridine–H); 13C
NMR (dc, CDCl3, 100 MHz): 14.6 (C8), 32.2 (C7), 36.4 (C9),
62.3 (C18), 63.4 (C17), 67.3 (C10), 114.6–155.5 (C11–C16),
122.3–157.3 (C2–C6), 115.7–158.6 (C20–C25), 163.5 (C19). Anal.
Calcd for C24H22N2O2FCl: C 67.84, H 5.22, N 6.59; found C
3-Chloro-1-(2,4-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (6e).
This compound was
obtained as off brown solid; yield, 58%; mp 147–148ꢀC. Rf:
0.72. IR nmax: 3054 (Ar–H), 2943, 2845 (ÀCH2–), 1722
(ÀC═O of b-lactam ring), 1225, 1026 (C–O–C), 745 (C–Cl);
1H NMR (d CDCl3, 400 MHz): 1.18 (t, 3H, –CH3), 2.53 (q, 2H,
–CH2), 3.12 (t, 2H, –CH2), 4.22 (t, 2H, –CH2–O), 5.12 (d, 1H,
–CH–Cl), 6.72–7.33 (m, 7H, Ar–H), 7.32–8.59 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.5 (C8), 32.5
(C7), 36.1 (C9), 62.2 (C18), 63.4 (C17), 67.5 (C10), 114.3–155.4
(C11–C16), 122.3–157.1 (C2–C6), 124.4–138.5 (C20–C25), 163.4
(C19). Anal. Calcd for C24H21N2O2Cl3: C 60.58, H 4.45, N
67.83, H 5.21, N 6.58.
3-Chloro-1-(3,5-difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
5.89; found C 60.57, H 4.46, N 5.90.
ethoxy)phenyl) azetidin-2-one (6b).
This compound was
3-Chloro-1-(3,4-difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
obtained as brown solid; yield, 49%; mp 120–122ꢀC. Rf: 0.72.
IR nmax: 3052 (Ar–H), 2942, 2845 (ÀCH2–), 1725 (ÀC═O of
b-lactam ring), 1225, 1026 (C–O–C), 745 (C–Cl), 973 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.12 (t, 3H, –CH3), 2.53 (q, 2H,
–CH2), 3.15 (t, 2H, –CH2), 4.30 (t, 2H, –CH2–O), 5.14 (d, 1H,
–CH–Cl), 6.66–7.22 (m, 7H, Ar–H), 7.30–8.63 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.5 (C8), 32.3
(C7), 36.4 (C9), 62.4 (C18), 63.5 (C17), 67.6 (C10), 114.3–155.1
(C11–C16), 122.1–157.0 (C2–C6), 100.0–164.5 (C20–C25), 163.2
(C19). Anal. Calcd for C24H21N2O2F2Cl: C 65.09, H 4.78, N
ethoxy)phenyl) azetidin-2-one (6f).
This compound was
obtained as brown solid; yield, 52%; mp 172–173ꢀC. Rf: 0.73.
IR nmax: 3052 (Ar–H), 2943, 2842 (ÀCH2–), 1728 (ÀC═O of
b-lactam ring), 1222, 1021 (C–O–C), 742 (C–Cl), 973 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.19 (t, 3H, –CH3), 2.49 (q, 2H,
–CH2), 3.16 (t, 2H, –CH2), 4.25 (t, 2H, –CH2–O), 5.16 (d, 1H,
–CH–Cl), 6.72–7.22 (m, 7H, Ar–H), 7.31–8.63 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.1 (C8), 32.5
(C7), 36.2 (C9), 62.4 (C18), 63.1 (C17), 67.3 (C10), 114.2–155.6
(C11–C16), 122.1–157.4 (C2–C6), 111.7–145.2 (C20–C25), 163.2
(C19). Anal. Calcd for C24H21N2O2F2Cl: C 65.09, H 4.78, N
6.33; found C 65.11, H 4.79, N 6.34.
3-Chloro-1-(4-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
6.33; found C 65.11, H 4.77, N 6.34.
ethoxy)phenyl)azetidin-2-one (6c).
This compound was
3-Chloro-1-(2-bromo-4-fluorophenyl)-4-(4-(2-(5-ethylpyridin-
obtained as brown liquid; yield, 54%; mp semi-solid. Rf: 0.71. IR
2-yl)ethoxy)phenyl) azetidin-2-one (6g).
This compound was
n
max: 3051 (Ar–H), 2940, 2845 (ÀCH2–), 1722 (ÀC═O of b-
obtained as brown solid; yield, 57%; mp 160–163ꢀC. Rf: 0.74. IR
lactam ring), 1222, 1021 (C–O–C), 743 (C–Cl); 1H NMR
(d CDCl3, 400MHz): 1.13 (t, 3H, –CH3), 2.52 (q, 2H, –CH2),
3.13 (t, 2H, –CH2), 4.25 (t, 2H, –CH2–O), 5.13 (d, 1H, –CH–Cl),
6.73–7.46 (m, 8H, Ar–H), 7.29–8.60 (m, 3H, Pyridine–H); 13C
NMR (dc, CDCl3, 100MHz): 14.2 (C8), 32.1 (C7), 36.5 (C9), 62.2
(C18), 63.1 (C17), 67.4 (C10), 114.2–155.3 (C11–C16), 122.2–157.3
n
max: 3055 (Ar–H), 2941, 2845 (ÀCH2–), 1723 (ÀC═O of b-
lactam ring), 1221, 1026 (C–O–C), 743 (C–Cl), 851 (C–Br), 974
(C–F); H NMR (d CDCl3, 400MHz): 1.15 (t, 3H, –CH3), 2.52
1
(q, 2H, –CH2), 3.17 (t, 2H, –CH2), 4.25 (t, 2H, –CH2–O), 5.21
(d, 1H, –CH–Cl), 6.72–7.22 (m, 7H, Ar–H), 7.32–8.64 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.3 (C8), 32.4
(C7), 36.3 (C9), 62.2 (C18), 63.5 (C17), 67.4 (C10), 114.7–155.5
(C11–C16), 122.6–157.2 (C2–C6), 114.5–160.2 (C20–C25), 163.4
(C19). Anal. Calcd for C24H21N2O2FClBr: C 57.22, H 4.20, N
5.56; found C 57.24, H, 4.21, N, 5.57.
3-Chloro-1-(3-chloro-4-methylphenyl)-4-(4-(2-(5-ethylpyridin-
2-yl)ethoxy)phenyl) azetidin-2-one (6h).
This compound was
obtained as dark brown solid; yield, 53%; mp 135–137ꢀC. Rf:
0.72. IR nmax: 3056 (Ar–H), 2943, 2841 (ÀCH2–), 1720 (ÀC═O
1
of b-lactam ring), 1228, 1026 (C–O–C), 747 (C–Cl); H NMR (d
CDCl3, 400MHz): 1.14 (t, 3H, –CH3), 2.20 (s, 3H, –CH3), 2.54
Figure 3. Azetidinone 6a–o.
(q, 2H, –CH2), 3.14 (t, 2H, –CH2), 4.30 (t, 2H, –CH2–O), 5.12 (d,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

784
N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
1H, –CH–Cl), 6.68–7.22 (m, 7H, Ar–H), 7.36–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.6 (C8), 20.5
(C26), 32.5 (C7), 36.2 (C9), 62.4 (C18), 63.6 (C17), 67.5 (C10),
114.3–155.2 (C11–C16), 122.2–157.4 (C2–C6), 119.5–140.2 (C20–
C25), 163.1 (C19). Anal. Calcd for C25H24Cl2N2O2: C 65.94, H
(ÀC═O of b-lactam ring), 1223, 1026 (C–O–C), 744 (C–Cl);
1H NMR (d CDCl3, 400 MHz): 1.16 (t, 3H, –CH3), 2.48 (q, 2H,
–CH2), 3.19 (t, 2H, –CH2), 4.25 (t, 2H, –CH2–O), 5.10 (d, 1H,
–CH–Cl), 6.72–7.75 (m, 7H, Ar–H), 7.31–8.62 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.2 (C8), 32.4
(C7), 36.3 (C9), 62.6 (C18), 63.4 (C17), 67.7 (C10), 114.3–155.5
(C11–C16), 122.3–157.4 (C2–C6), 121.1–141.5 (C20–C25), 163.0
(C19). Anal. Calcd for C24H21N2O2Cl3: C 60.58, H 4.45, N
5.31, N 6.15; found C 65.96, H 5.34, N, 6.14.
3-Chloro-1-(3,5-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (6i).
This compound was
obtained as brown solid; yield, 65%; mp 155–156ꢀC. Rf: 0.75.
IR nmax: 3052 (Ar–H), 2943, 2842 (ÀCH2–), 1721 (ÀC═O of
5.89; found C 60.59, H 4.47, N 5.89.
3-Chloro-1-(3-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
1
ethoxy)phenyl)azetidin-2-one (6n).
This compound was
b-lactam ring), 1225, 1025 (C–O–C), 744 (C–Cl); H NMR (d
obtained as brown solid; yield, 60%; mp 118–120ꢀC. Rf: 0.76.
IR nmax: 3053 (Ar–H), 2945, 2846 (ÀCH2–), 1724 (ÀC═O of
CDCl3, 400 MHz): 1.16 (t, 3H, –CH3), 2.54 (q, 2H, –CH2), 3.12
(t, 2H, –CH2), 4.24 (t, 2H, –CH2–O), 5.18 (d, 1H, –CH–Cl),
6.72–7.23 (m, 7H, Ar–H), 7.35–8.68 (m, 3H, Pyridine–H); 13C
NMR (dc, CDCl3, 100 MHz): 14.7 (C8), 32.5 (C7), 36.1 (C9),
62.1 (C18), 63.3 (C17), 67.6 (C10), 114.3–155.2 (C11–C16),
122.3–157.5 (C2–C6), 120.2–144.2 (C20–C25), 163.2 (C19).
Anal. Calcd for C24H21N2O2Cl3: C 60.58, H 4.45, N 5.89;
1
b-lactam ring), 1222, 1023 (C–O–C), 746 (C–Cl); H NMR (d
CDCl3, 400 MHz): 1.18 (t, 3H, –CH3), 2.54 (q, 2H, –CH2), 3.17
(t, 2H, –CH2), 4.26 (t, 2H, –CH2–O), 5.11 (d, 1H, –CH–Cl),
6.72–7.40 (m, 8H, Ar–H), 7.34–8.64 (m, 3H, Pyridine–H); 13C
NMR (dc, CDCl3, 100 MHz): 14.7 (C8), 32.5 (C7), 36.6 (C9),
62.3 (C18), 63.3 (C17), 67.5 (C10), 114.2–155.1 (C11–C16),
122.4–157.5 (C2–C6), 119.5–143.1 (C20–C25), 163.2 (C19).
Anal. Calcd for C24H22N2O2Cl2: C 65.31, H 5.02, N 6.35;
found C 60.57, H 4.43, N 5.90.
3-Chloro-1-(2-chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (6j).
This compound was
found C 65.30, H 5.03, N 6.34.
obtained as brown limpid; yield, 60%; mp semi-solid. Rf: 0.74.
3-Chloro-1-(4-methylphenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
IR nmax: 3053 (Ar–H), 2947, 2840 (ÀCH2–), 1722 (ÀC═O of
1
ethoxy)phenyl)azetidin-2-one (6o).
This compound was
b-lactam ring), 1225, 1027 (C–O–C), 746 (C–Cl); H NMR (d
obtained as brown solid; yield, 69%; mp 142–144ꢀC. Rf: 0.74.
IR nmax: 3052 (Ar–H), 2942, 2845 (ÀCH2–), 1725 (ÀC═O of b-
lactam ring), 1225, 1026 (C–O–C), 745 (C–Cl); 1H NMR (d
CDCl3, 400MHz): 1.12 (t, 3H, –CH3), 2.13 (s, 3H, –CH3), 2.52
(q, 2H, –CH2), 3.15 (t, 2H, –CH2), 4.29 (t, 2H, –CH2–O), 5.15
(d, 1H, –CH–Cl), 6.85–7.35 (m, 8H, Ar–H), 7.33–8.30 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100MHz): 14.7 (C8), 25.0
(C26), 32.5 (C7), 36.5 (C9), 62.5 (C18), 63.2 (C17), 67.3 (C10),
114.7–155.4 (C11–C16), 123.4–158.8 (C2–C6), 120.7–137.2 (C20–
C25), 162.4 (C19). Anal. Calcd for C25H25N2O2Cl: C 71.33, H
CDCl3, 400 MHz): 1.19 (t, 3H, –CH3), 2.51 (q, 2H, –CH2), 3.14
(t, 2H, –CH2), 4.32 (t, 2H, –CH2–O), 5.13 (d, 1H, –CH–Cl),
6.72–7.52 (m, 8H, Ar–H), 7.32–8.64 (m, 3H, Pyridine–H); 13C
NMR (dc, CDCl3, 100 MHz): 14.3 (C8), 32.8 (C7), 36.3 (C9),
62.8 (C18), 63.7 (C17), 67.2 (C10), 114.5–155.6 (C11–C16),
122.4–157.0 (C2–C6), 123.2–140.2 (C20–C25), 163.2 (C19).
Anal. Calcd for C24H22N2O2Cl2: C 65.31, H 5.02, N 6.35;
found C 65.33, H 5.04, N 6.34.
3-Chloro-1-(2-flourophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)azetidin-2-one (6k).
This compound was
5.99, N 6.66; found C 71.32, H 5.97, N 6.65.
obtained as brown limpid; yield, 58%; mp semi-solid. Rf: 0.71.
IR nmax: 3058 (Ar–H), 2944, 2843 (ÀCH2–), 1724 (ÀC═O of
b-lactam ring), 1226, 1023 (C–O–C), 747 (C–Cl), 975 (C–F);
1H NMR (d CDCl3, 400 MHz): 1.18 (t, 3H, –CH3), 2.55 (q, 2H,
–CH2), 3.13 (t, 2H, –CH2), 4.22 (t, 2H, –CH2–O), 5.16 (d, 1H,
–CH–Cl), 6.72–7.25 (m, 8H, Ar–H), 7.33–8.63 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.5 (C8), 32.6
(C7), 36.4 (C9), 62.5 (C18), 63.6 (C17), 67.4 (C10), 114.3–155.4
(C11–C16), 122.5–157.3 (C2–C6), 123.2–163.2 (C20–C25), 162.5
(C19). Anal. Calcd for C24H22N2O2FCl: C 67.84, H 5.22, N
General preparation of the compounds (7a–o). A mixture
of Schiff base (0.01 mol) and phenoxyacetic acid (0.01 mol) was
dissolved in dry benzene (20 mL) with constant stirring, and
thionyl chloride (10 mL) was added to a mixture at 0ꢀC. After
the complete addition, a solid mass separated out and stir it for
2–4 h, which was filtered off, dried in vacuo, and recrystallized
from ethanol (Scheme-2) (Figure-4).
1-(4-Fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7a).
This compound was
obtained as yellow solid; yield, 75%; mp 125–127ꢀC. Rf: 0.82.
IR nmax: 3045 (Ar–H), 2942, 2851 (ÀCH2–), 1725 (ÀC═O of
6.59; found C 67.86, H 5.23, N 6.58.
3-Chloro-1-(2,5-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (6l).
This compound was
obtained as dark brown liquid; yield, 62%; mp semi-solid. Rf:
0.72. IR nmax: 3056 (Ar–H), 2949, 2845 (ÀCH2–), 1726
(ÀC═O of b-lactam ring), 1224, 1025 (C–O–C), 743 (C–Cl);
1H NMR (d CDCl3, 400 MHz): 1.16 (t, 3H, –CH3), 2.52 (q, 2H,
–CH2), 3.20 (t, 2H, –CH2), 4.26 (t, 2H, –CH2–O), 5.17 (d, 1H,
–CH–Cl), 6.72–7.55 (m, 7H, Ar–H), 7.36–8.66 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 14.6 (C8), 32.3
(C7), 36.5 (C9), 62.2 (C18), 63.1 (C17), 67.3 (C10), 114.2–155.4
(C11–C16), 122.5–157.3 (C2–C6), 123.4–140.5 (C20–C25), 163.5
(C19). Anal. Calcd for C24H21N2O2Cl3: C 60.58, H 4.45, N
5.89; found C 60.59, H 4.46, N 5.88.
3-Chloro-1-(2,5-dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl) azetidin-2-one (6m).
This compound was
obtained as dark brown liquid; yield, 63%; mp semi-solid. Rf:
0.74. IR nmax: 3055 (Ar–H), 2948, 2845 (ÀCH2–), 1725
Figure 4. Azetidinone 7a–o.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2014
New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
785
b-lactam ring), 1234, 1025 (C–O–C), 974 (C–F); 1H NMR (d
CDCl3, 400 MHz): 1.34 (t, 3H, –CH3), 2.85 (q, 2H, –CH2), 3.84
(t, 2H, –CH2), 4.52 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH of aze),
5.32 (s, 1H, –CH), 6.74–7.28 (m, 13H, Ar–H), 7.19–8.65 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.4 (C8),
33.4 (C7), 36.2 (C9), 60.2 (C17), 67.5 (C10), 80.2 (C18),
114.2–157.5 (C11–C16), 123.2–158.4 (C2–C6), 115.6–158.5
(C20–C25), 165.1 (C19), 114.5–148.6 (C27–C32). Anal. Calcd
165.2 (C19), 114.5–148.4 (C27–C32). Anal. Calcd for
C30H26N2O3Cl2: C 67.55, H 4.91, N 5.25; found C 67.56, H
4.92, N 5.26.
1-(3,4-Difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7f).
This compound was
obtained as yellow solid; yield, 81%; mp 160–162ꢀC. Rf: 0.78.
IR nmax: 3048 (Ar–H), 2944, 2852 (ÀCH2–), 1729 (ÀC═O of
b-lactam ring), 1232, 1024 (C–O–C), 975 (C–F); 1H NMR (d
CDCl3, 400 MHz): 1.34 (t, 3H, –CH3), 2.85 (q, 2H, –CH2), 3.82
(t, 2H, –CH2), 4.54 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH of aze),
5.31 (s, 1H, –CH), 6.72–7.25 (m, 12H, Ar–H), 7.22–8.66 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.1 (C8),
33.3 (C7), 36.2 (C9), 60.1 (C17), 67.4 (C10), 80.4 (C18),
114.2–157.3 (C11–C16), 123.1–158.3 (C2–C6), 111.4–150.0
(C20–C25), 165.4 (C19), 114.2–148.6 (C27–C32). Anal. Calcd
for C30H26F2N2O3: C 71.99, H 5.24, N 5.60; found C 71.98,
for C30H27N2O3F:
74.66, H 5.66, N 5.80.
1-(3,5-Difluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7b). This compound was
C 74.67, H 5.64, N 5.81; found C
obtained as yellow solid; yield, 78%; mp 129–132ꢀC. Rf: 0.83.
IR nmax: 3045 (Ar–H), 2942, 2851 (ÀCH2–), 1725 (ÀC═O of
b-lactam ring), 1234, 1025 (C–O–C), 974 (C–F); 1H NMR (d
CDCl3, 400 MHz): 1.32 (t, 3H, –CH3), 2.81 (q, 2H, –CH2), 3.82
(t, 2H, –CH2), 4.50 (t, 2H, –CH2–O), 5.33 (s, 1H, –CH of aze),
5.31 (s, 1H, –CH), 6.58–7.27 (m, 12H, Ar–H), 7.20–8.66 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.5 (C8),
33.2 (C7), 36.4 (C9), 60.1 (C17), 67.6 (C10), 80.4 (C18),
114.1–157.2 (C11–C16), 123.4–158.3 (C2–C6), 100.6–164.5
(C20–C25), 165.3 (C19), 114.2–148.1 (C27–C32). Anal. Calcd
for C30H26F2N2O3: C 71.99, H 5.24, N 5.60; found C
H 5.25, N 5.62.
1-(2-Bromo-4-fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)-3-phenoxy azetidin-2-one (7g).
This
compound was obtained as yellow solid; yield, 75%; mp 155–
156ꢀC. Rf: 0.81. IR nmax: 3045 (Ar–H), 2942, 2851 (ÀCH2–),
1725 (ÀC═O of b-lactam ring), 1234, 1025 (C–O–C), 974 (C–F),
1
855 (C–Br); H NMR (d CDCl3, 400 MHz): 1.30 (t, 3H, –CH3),
2.81 (q, 2H, –CH2), 3.80 (t, 2H, –CH2), 4.52 (t, 2H, –CH2–O),
5.31 (s, 1H, –CH of aze), 5.24 (s, 1H, –CH), 6.72–7.27 (m, 12H,
Ar–H), 7.27–8.69 (m, 3H, Pyridine–H); 13C NMR (dc, CDCl3,
100 MHz): 19.3 (C8), 33.2 (C7), 36.4 (C9), 60.3 (C17), 67.5
(C10), 80.1 (C18), 114.5–157.4 (C11–C16), 123.3–158.1 (C2–C6),
114.4-160.1 (C20–C25), 165.4 (C19), 114.2–148.6 (C27–C32).
Anal. Calcd for C30H26N2O3FBr: C 64.18, H 4.67, N 4.99;
71.97, H 5.23, N 5.62.
1-(4-Chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)-
3-phenoxy azetidin-2-one (7c). This compound was obtained as
yellow solid; yield, 83%; mp 132–133ꢀC. Rf: 0.85. IR nmax: 3041
(Ar–H), 2945, 2852 (ÀCH2–), 1727 (ÀC═O of b-lactam ring),
1233, 1026 (C–O–C), 746 (C–Cl); 1H NMR (d CDCl3,
400 MHz): 1.36 (t, 3H, –CH3), 2.83 (q, 2H, –CH2), 3.84 (t,
2H, –CH2), 4.52 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH of aze), 5.30
(s, 1H, –CH), 6.72–7.47 (m, 13H, Ar–H), 7.24–8.65 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100MHz): 19.2 (C8), 33.3
(C7), 36.2 (C9), 60.2 (C17), 67.4 (C10), 80.3 (C18), 114.5–157.3
(C11–C16), 123.2–158.4 (C2–C6), 123.1–139.8 (C20–C25), 165.4
(C19), 114.4–148.2 (C27–C32). Anal. Calcd for C30H27N2O3Cl: C
found C 64.19, H 4.65, N 4.98.
1-(3-Chloro-4-methylphenyl)-4-(4-(2-(5-ethylpyridin-2-yl)
ethoxy)phenyl)-3-phenoxy azetidin-2-one (7h):.
This
compound was obtained as yellow solid; yield, 77%;
mp 143–145ꢀC. Rf: 0.77. IR nmax: 3041 (Ar–H), 2945, 2852
(ÀCH2–), 1727 (ÀC═O of b-lactam ring), 1230, 1026 (C–O–C),
1
746 (C–Cl); H NMR (d CDCl3, 400 MHz): 1.35 (t, 3H, –CH3),
72.21, H 5.45, N 5.61; found C 72.20, H 5.44, N 5.60.
1-(3,4-Dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7d).
2.32 (s, 3H, –CH3), 2.84 (q, 2H, –CH2), 3.84 (t, 2H, –CH2), 4.56
(t, 2H, –CH2–O), 5.32 (s, 1H, –CH of aze), 5.25 (s, 1H, –CH),
6.80–7.29 (m, 12H, Ar–H), 7.15–8.65 (m, 3H, Pyridine–H);
13C NMR (dc, CDCl3, 100 MHz): 19.3 (C8), 25.6 (C26),
33.4 (C7), 36.6 (C9), 60.2 (C17), 67.4 (C10), 80.2 (C18),
114.7–157.6 (C11–C16), 123.4–158.5 (C2–C6), 119.6–140.2
(C20–C25), 165.3 (C19), 114.7–148.8 (C27–C32). Anal. Calcd
for C31H29N2O3Cl: C 72.58, H 5.70, N 5.46; found C 72.57,
This compound was
obtained as yellow solid; yield, 85%; mp 145–147ꢀC. Rf: 0.80.
IR nmax: 3044 (Ar–H), 2941, 2854 (ÀCH2–), 1726 (ÀC═O of
b-lactam ring), 1234, 1025 (C–O–C), 745 (C–Cl); 1H NMR
(d CDCl3, 400 MHz): 1.35 (t, 3H, –CH3), 2.80 (q, 2H, –CH2),
3.81 (t, 2H, –CH2), 4.55 (t, 2H, –CH2–O), 5.33 (s, 1H, –CH of
aze), 5.29 (s, 1H, –CH), 6.72–7.27 (m, 12H, Ar–H), 7.25–8.62
(m, 3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.4
(C8), 33.4 (C7), 36.3 (C9), 60.3 (C17), 67.5 (C10), 80.2 (C18),
114.2–157.4 (C11–C16), 123.4–158.6 (C2–C6), 121.4–141.3
(C20–C25), 165.1 (C19), 114.4–148.2 (C27–C32). Anal. Calcd for
C30H26N2O3Cl2: C 67.55, H 4.91, N 5.25; found C 67.53, H
H 5.71, N 5.45.
1-(3,5-Dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7i).
This compound was
obtained as yellow solid; yield, 82%; mp 123–125ꢀC. Rf: 0.77.
IR nmax: 3046 (Ar–H), 2946, 2852 (ÀCH2–), 1724 (ÀC═O of
1
b-lactam ring), 1232, 1027 (C–O–C), 746 (C–Cl); H NMR (d
4.90, N 5.23.
1-(2,4-Dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
CDCl3, 400 MHz): 1.29 (t, 3H, –CH3), 2.82 (q, 2H, –CH2), 3.83
(t, 2H, –CH2), 4.51 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH of aze),
5.30 (s, 1H, –CH), 6.73–7.26 (m, 12H, Ar–H), 7.26–8.70 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.6 (C8),
33.4 (C7), 36.2 (C9), 60.7 (C17), 67.1 (C10), 80.2 (C18),
114.6–157.2 (C11–C16), 123.4–158.3 (C2–C6), 120.4–141.5
(C20–C25), 165.3 (C19), 114.4–148.4 (C27–C32). Anal. Calcd
for C30H26N2O3Cl2: C 67.55, H 4.91, N 5.25; found C 67.56,
phenyl)-3-phenoxy azetidin-2-one (7e).
This compound was
obtained as yellow solid; yield, 86%; mp 151–152ꢀC. Rf: 0.79.
IR nmax: 3047 (Ar–H), 2943, 2850 (ÀCH2–), 1730 (ÀC═O of
1
b-lactam ring), 1231, 1022 (C–O–C), 746 (C–Cl); H NMR (d
CDCl3, 400 MHz): 1.33 (t, 3H, –CH3), 2.82 (q, 2H, –CH2), 3.84
(t, 2H, –CH2), 4.51 (t, 2H, –CH2–O), 5.32 (s, 1H, –CH of aze),
5.30 (s, 1H, –CH), 6.72–7.28 (m, 12H, Ar–H), 7.20–8.64 (m, 3H,
Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.3 (C8), 33.5
(C7), 36.1 (C9), 60.4 (C17), 67.3 (C10), 80.3 (C18), 114.0–157.1
(C11–C16), 123.2–158.4 (C2–C6), 124.4–138.3 (C20–C25),
H 4.92, N 5.26.
1-(2-Chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7j).
This compound was
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

786
N. B. Patel, H. R. Patel, F. M. Shaikh, and D. Rajani
Vol 51
obtained as yellow limpid; yield, 86%; mp limpid. Rf: 0.78. IR
(m, 3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.7
(C8), 33.5 (C7), 36.3 (C9), 60.4 (C17), 67.2 (C10), 80.1 (C18),
114.4–157.0 (C11–C16), 123.3–158.3 (C2–C6), 119.5–143.5
(C20–C25), 165.4 (C19), 114.2–148.5 (C27–C32). Anal. Calcd for
C30H27N2O3Cl: C 72.21, H 5.45, N 5.61; found C 72.23, H
n
max: 3048 (Ar–H), 2945, 2854 (ÀCH2–), 1725 (ÀC═O of b-
lactam ring), 1235, 1026 (C–O–C), 742 (C–Cl; 1H NMR (d
CDCl3, 400 MHz): 1.32 (t, 3H, –CH3), 2.86 (q, 2H, –CH2), 3.85
(t, 2H, –CH2), 4.53 (t, 2H, –CH2–O), 5.32 (s, 1H, –CH of aze),
5.26 (s, 1H, –CH), 6.72–7.26 (m, 13H, Ar–H), 7.26–8.70 (m,
3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.8 (C8),
33.6 (C7), 36.1 (C9), 60.2 (C17), 67.3 (C10), 80.4 (C18),
114.5–157.4 (C11–C16), 123.0–158.4 (C2–C6), 123.4–140.5
(C20–C25), 165.4 (C19), 114.7–148.5 (C27–C32). Anal. Calcd
for C30H27N2O3Cl: C 72.21, H 5.45, N 5.61; found C 72.23,
5.44, N 5.62.
1-(4-Methylphenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7o).
This compound was
obtained as yellow solid; yield, 83%; mp 135–137ꢀC. Rf: 0.78.
IR nmax: 3042 (Ar–H), 2948, 2852 (ÀCH2–), 1722 (ÀC═O of
b-lactam ring), 1232, 1020 (C–O–C); 1H NMR (d CDCl3,
400 MHz): 1.32 (t, 3H, –CH3), 2.34 (s, 3H, –CH3), 2.86 (q, 2H,
–CH2), 3.82 (t, 2H, –CH2), 4.58 (t, 2H, –CH2–O), 5.31 (d, 1H,
–CH of aze), 5.29 (d, 1H, –CH), 7.03–8.33 (m, 13H, Ar–H),
7.16–8.61 (m, 3H, Pyridine–H); 13C NMR (dc, CDCl3,
100 MHz): 19.5 (C8), 25.7 (C26), 33.5 (C7), 36.4 (C9), 60.6
(C17), 67.3 (C10), 80.1 (C18), 114.5–157.7 (C11–C16), 123.1–158.2
(C2–C6), 120.6–137.2 (C20–C25), 165.1 (C19), 114.6–148.7
(C27–C32). Anal. Calcd for C31H30N2O3: C 77.80, H 6.32, N
5.85; found C 77.81, H 6.33, N 5.84.
H 5.46, N 5.62.
1-(2-Fluorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7k).
This compound was
obtained as yellow limpid; yield, 82%; mp limpid. Rf: 0.79. IR
n
max: 3043 (Ar–H), 2944, 2852 (ÀCH2–), 1728 (ÀC═O of
1
b-lactam ring), 1237, 1026 (C–O–C), 973 (C–F); H NMR (d
CDCl3, 400 MHz): 1.35 (t, 3H, –CH3), 2.84 (q, 2H, –CH2),
3.82 (t, 2H, –CH2), 4.56 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH of
aze), 5.27 (s, 1H, –CH), 6.72–7.27 (m, 13H, Ar–H), 7.26–8.75
(m, 3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.5
(C8), 33.4 (C7), 36.6 (C9), 60.4 (C17), 67.1 (C10), 80.3 (C18),
114.8–157.0 (C11–C16), 123.2–158.1 (C2–C6), 115.4–163.1
(C20–C25), 165.4 (C19), 114.7–148.5 (C27–C32). Anal. Calcd
for C30H27N2O3F: C 74.67, H 5.64, N 5.81; found C 74.66, H
Acknowledgments. The authors thank the Department of Chemistry
for laboratory facilities and the Librarian of Veer Narmad South
Gujarat University, Surat for library facilities. They also thank
Atul Ltd. for IR spectra, C.D.R.I., Lucknow for elemental
analysis, and S.A.I.F., Chandigarh for 1H NMR and13C NMR
spectral analyses.
5.65, N 5.82.
1-(2,5-Dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7l).
This compound was
obtained as yellow limpid; yield, 84%; mp limpid. Rf: 0.80. IR
n
max: 3046 (Ar–H), 2942, 2857 (ÀCH2–), 1726 (ÀC═O of
1
b-lactam ring), 1234, 1028 (C–O–C), 746 (C–Cl); H NMR (d
CDCl3, 400 MHz): 1.32 (t, 3H, –CH3), 2.79 (q, 2H, –CH2),
3.82 (t, 2H, –CH2), 4.54 (t, 2H, –CH2–O), 5.32 (s, 1H, –CH of
aze), 5.28 (s, 1H, –CH), 6.72–7.55 (m, 12H, Ar–H), 7.25–8.68
(m, 3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.2
(C8), 33.2 (C7), 36.3 (C9), 60.6 (C17), 67.4 (C10), 80.1 (C18),
114.6–157.2 (C11–C16), 123.4–158.3 (C2–C6), 123.4–141.1
(C20–C25), 165.0 (C19), 114.8–148.9 (C27–C32). Anal. Calcd
for C30H26N2O3Cl2: C 67.55, H 4.91, N 5.25; found C 67.56,
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H 4.92, N 5.24.
1-(2,3-Dichlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
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IR nmax: 3048 (Ar–H), 2945, 2853 (ÀCH2–), 1728 (ÀC═O
of b-lactam ring), 1233, 1029 (C–O–C), 743 (C–Cl); 1H
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CH2), 3.83 (t, 2H, –CH2), 4.52 (t, 2H, –CH2–O), 5.34 (s, 1H, –CH
of aze), 5.30 (s, 1H, –CH), 6.73–7.76 (m, 12H, Ar–H), 7.24–8.66
(m, 3H, Pyridine–H); 13C NMR (dc, CDCl3, 100 MHz): 19.4 (C8),
33.2 (C7), 36.6 (C9), 60.2 (C17), 67.0 (C10), 80.4 (C18),
114.1–157.4 (C11–C16), 123.2–158.5 (C2–C6), 121.2–141.5
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67.57, H 4.93, N 5.26.
1-(3-Chlorophenyl)-4-(4-(2-(5-ethylpyridin-2-yl)ethoxy)
phenyl)-3-phenoxy azetidin-2-one (7n).
obtained as yellow limpid; yield, 85%; mp limpid. Rf: 0.76. IR
This compound was
n
max: 3044 (Ar–H), 2942, 2856 (ÀCH2–), 1729 (ÀC═O of b-
lactam ring), 1235, 1026 (C–O–C), 745 (C–Cl); 1H NMR
(d CDCl3, 400 MHz): 1.36 (t, 3H, –CH3), 2.84 (q, 2H, –CH2),
3.81 (t, 2H, –CH2), 4.53 (t, 2H, –CH2–O), 5.32 (s, 1H, –CH of
aze), 5.25 (s, 1H, –CH), 6.73–7.28 (m, 13H, Ar–H), 7.25–8.68
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2014
New Azetidin-2-ones of 5-Ethyl Pyridine-2-ethanol
787
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet