Synthesis, spectral, and antimicrobial studies of 1-butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones

Article abstract of DOI:10.1002/hc.20052

Ketene generated from acetyl chloride or chloroacetyl chloride adds on indolyl Schiff's base double bond to afford 1-butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones in THF. The reaction proceeds stereospecifically via concerted trans cycloaddi

Full text of DOI:10.1002/hc.20052

Heteroatom Chemistry
Volume 15, Number 7, 2004
Synthesis, Spectral, and Antimicrobial Studies
of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-
3-yl)-2-azetidinones
Vijai N. Pathak,1 Ragini Gupta,2 and Meenu Garg1
1Department of Chemistry, University of Rajasthan, Jaipur 302004, India
2Department of Chemistry, Malaviya National Institute of Technology, Jaipur 302017, India
Received 10 March 2004
lizing effects [9], neuroplegic action [10], antitumor
ABSTRACT: Ketene generated from acetyl chloride or
activity [11], and antimetastatic activity [12], indole
chloroacetyl chloride adds on indolyl Schiff’s base dou-
derivatives also display a wide range of antimicrobial
ble bond to afford 1-butyl-3-substituted-4-(2-aryl-1H-
activities [13,14]. It is therefore considered to link the
indol-3-yl)-2-azetidinones in THF. The reaction pro-
ꢀ-lactam moiety with indole moiety in search of bet-
ceeds stereospecifically via concerted trans [2+2] cy-
ter antimicrobial agents. Keeping these observations
cloaddition. The synthesized compounds have been
in view, we have undertaken a comprehensive pro-
characterized by elemental analyses and spectral data
gram for developing better antimicrobial agents, and
(IR, PMR, and mass). All synthesized compounds
have synthesized 1-butyl-3-substitutated-4-(2-aryl-
have been evaluated for antibacterial and antifungal
1H-indol-3-yl)-2-azetidinones and screened them for
activities, and 4g to 4l have shown promising re-
their antibacterial and antifungal activities.
ꢀ
C
sults.
2004 Wiley Periodicals, Inc. Heteroatom Chem
15:494–501, 2004; Published online in Wiley InterScience
(www.interscience.wiley.com). DOI 10.1002/hc.20052
RESULTS AND DISCUSSION
Synthesis
2-Arylindole 1 was subjected to Vilsmeier–Haack
formylation [15] with POCl3 and N,N-dimethyl for-
mamide to give 2-arylindole-3-carboxaldehyde 2.
This, 3-formylindole 2 was condensed with butyl-
amine, in refluxing toluene, to give 3-butylimino-
methyl-2-arylindole (Schiff’s base, 3). This 2-butyl-
iminomethyl-2-arylindole 3 was chloroacetylated/
acetylated with chloroacetyl chloride or acetyl chlo-
ride in the presence of triethylamine and THF. The
four-membered ring formation takes place via con-
certed trans [2+2] thermal cycloaddition reaction to
afford the desired compound 4 (Scheme 1).
INTRODUCTION
ꢀ-Lactam antibiotics are well known for their antimi-
crobial activity (e.g. penicillin and cephalosporins)
[1,2], lowering cholesterol level [3,4], serine protease
inhibition [5], tubercular activity, and chemothera-
peutic activities [6]. Recently, ꢀ-lactams have been
used as synthons in the preparation of various hete-
rocyclic compounds of biological significance [7].
In addition to various psychopharmacological
activities viz., CNS-depressant activities [8], tranqui-
The physical and analytical data of compounds
(4a–l) are given in (Table 1).
In the IR spectra of 2-aryl-1H-indol-3-carbo-
xaldehydes, >N H absorption appears as a broad
Correspondence to: Vijai N. Pathak; e-mail: pathakvijain@yahoo.
com.
Contract grant sponsor: UGC.
2004 Wiley Periodicals, Inc.
c
ꢀ
494

Synthesis, Spectral, and Antimicrobial Studies of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones 495
SCHEME 1
band from 3220–3140 cm−1. Characteristic absorp-
tion due to >C O of formyl group appears at 1625
cm−1. This downfield shift from the normal >C O
absorption (1720 cm−1) is attributed to the pres-
ence of high degree of conjugation in the formy-
In the IR spectra of 3-butyliminomethyl-2-aryl-
1H-indoles (Schiff’s base), >N H absorption ap-
pears as a broad band from 3250–3180 cm−1.
Characteristic absorption due to >C N group ap-
pears at 1630–1620 cm−1. In the 1H NMR of 3-
butyliminomethyl-2-aryl-1H-indoles, CH N pro-
ton resonance signal appears as a sharp singlet at
δ 8.0–8.2 ppm. This upfield shift confirms the con-
version of formyl group ( CHO) into imino group
(HC N ).
1
lated indole. In the H NMR of 2-aryl-1H-indol-3-
carboxaldehydes C H proton resonance signal of
formyl group appears as a sharp singlet at δ 8.45
ppm. Aromatic and >N H proton signals appear as
multiplet from δ 6.8 to 7.7 ppm.
TABLE 1 The Physical and Analytical Data of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinone
Found (Calcd) (%)
H
Molecular
Weight
Melting
Compound
X
Y
H
Molecular Formula
Point ( ◦C) Yield %
C
N
4a
4b
4c
4d
4e
4f
H
C21H22N2O
318
397
352
336
332
370
352
431
386
370
366
404
67
122
154
140
98
73
71
68
75
80
69
72
67
68
75
81
79
78.38
(79.24)
63.60
(63.63)
71.32
6.73
(6.96)
5.28
(5.30)
5.90
8.88
(8.80)
7.01
(7.07)
7.81
(7.94)
8.30
(8.33)
8.46
(8.46)
7.59
(7.55)
7.91
(7.94)
6.58
(6.51)
7.20
(7.25)
7.53
(7.55)
7.62
(7.65)
6.90
(6.93)
4-Br
4-Cl
H
C
C
21H21BrN2O
21H21CIN2O
H
(71.48)
75.04
(75.00)
79.45
(5.95)
6.20
(6.25)
7.12
4-F
H
C21H21FN2O
4-CH3
3-Cl, 4-F
H
H
C22H24N2O
(79.51)
68.08
(68.01)
71.32
(7.22)
5.29
(5.39)
5.93
H
C
21H20ClFN2O
172
218
183
200
138
90
4g
4h
4i
Cl
Cl
Cl
Cl
Cl
C21H21ClN2O
(71.48)
58.66
(58.60)
65.15
(5.95)
4.75
(4.65)
5.08
4-Br
4-Cl
C21H20BrClN2O
C
21H20Cl2N2O
(65.28)
68.02
(68.01)
72.01
(5.18)
5.32
(5.39)
6.12
4j
4-F
C21H20ClFN2O
4k
4l
4-CH3
C22H23ClN2O
21H19Cl2FN2O
(72.03)
62.36
(62.37)
(6.28)
4.65
(4.70)
3-Cl, 4-F Cl
C
164

496 Pathak, Gupta, and Garg
In the IR spectra of 1-butyl-3-chloro-4-[2-aryl-
1H-indol-3-yl]-2-azetidinone and 1-butyl-4-[2-aryl-
1H-indol-3-yl]-2-azetidinone, >N H absorption ap-
pears as a sharp band at 3323 cm−1. Characteristic
absorption due to ꢀ-lactam >C O appears at 1750
cm−1. The absorption due to C Cl and C Br ap-
pears at 748 cm−1 and 499 cm−1, respectively. In the
1H NMR spectra, CH N< proton resonance sig-
This downfield triplet shows that methylene group is
attached to azetidinone ring.
A possible mechanism is given in Scheme 2.
1
The IR and H NMR data of 1-butyl-3-substi-
tuted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones are
summarized in Table 2.
Final confirmation is obtained from fast atomic
bombardment (FAB) mass spectra as M+ at 318 4(a),
332 4(e), and 432 4(h) that correspond to their mole-
cular masses which are C21H22N2O, C22H24N2O, and
C21H2079Br35ClN2O respectively (Table 3).
nal appears as double doublet at δ 4.8 ppm (JHaHb
=
1.66 Hz). A sharp azetidinonic double doublet due to
CH Cl group appears at δ 5.0 ppm (JHaHb = 1.66 Hz).
This downfield shift is attributed to the highly elec-
tron withdrawing groups flanked on either side. It
shows a conrotatory [2+2] cycloaddition yielding
the trans ꢀ-lactam isomer [16]. This isomer contains
two chiral centers (one carbon and another nitro-
gen). The >N H proton signal of indole moiety ap-
pears as sharp singlet at δ 8.8 ppm. Aromatic pro-
ton signals appear as multiplet at δ 7.2–δ 7.5 ppm.
Triplet of methyl ( CH3) group appears at δ 0.7 ppm.
CH3 CH2 and CH2 CH2 N appear as multiplets at
δ 1.1 and δ 1.6 ppm respectively.
The mass fragmentation of compound 4(h) is
discussed in detail. Compound 4(h) (Scheme 3) un-
der FAB provides a characteristic molecular ion clus-
ter at 430/432 I (100%, base peak) due to the presence
of one bromine and one chlorine atom. This may
fragment by two pathways A and B. In the pathway
A, I eliminates a chlorine radical to generate a cation
II m/z 395/397 (50%); removal of chlorine radical is
confirmed by the peak ratio being 1:1 showing the
isotopic abundance of bromine atom alone in cation
II. Cation II by loss of neutral cyclopropane moiety
yields cation III at m/z 353/355 (52%). Cation III
eliminates cyclobutadiene to give cation VI at m/z
A triplet is observed downfield at δ 3.6 ppm due to
methylene ( CH2) group attached to nitrogen atom.
SCHEME 2

Synthesis, Spectral, and Antimicrobial Studies of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones 497
TABLE 2 Spectral Data of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones
Compound
IR (KBr)vmax (cm−1
)
1H NMR (CDCl3) δ (ppm)
Mass m/z
4a
3403 (NH str.), 3050 (aromatic C H
str.), 2839 (aliphatic C H str.), 1750
(>C O), 1657 (aromatic C C str.),
1601 (C C str.).
8.4 (s, NH, 1H), 7.3–7.5 (m, Ar-H, 5H), 5.1
(dd, CH N, 1H, J HaHb = 1.68) (trans), 5.4
(dd, CHa CO, 1H, J HaHb = 1.68) (trans), 3.6
(m, N CH2, 2H), 1.8–2.0(m, CH2 CH2,
4H), 0.09 (t, CH3, 3H).
8.8 (s, NH, 1H), 7.2–7.4 (m, Ar H), 5.6
(dd, CH CO, 1H), 5.0 (dd, CH N, 1H), 2.4
(t, N CH2, 2H), 1.6–2.0 (m, CH2 CH2, 4H),
0.1 (t, CH3, 3H).
8.8 (s, NH, 1H), 7.6 (d, Ar H, 2H, J = 8.4 Hz),
7.5 (d, Ar H, 2H, J = 8.4 Hz), 5.0 (dd,
CHa Cl, 1H, J HaHb = 1.66 Hz) (trans), 4.8
(dd, CHb N, 1H, J HaHb = 1.66 Hz) (trans),
3.6 (m, N CH2, 2H), 1.1–1.6 (m, CH2 CH2,
4H), 0.7 (t, CH3, 3H).
318 (m+)
4e
4h
3416 (NH str.), 3049 (aromatic C H),
2839 (aliphatic C H str.), 1716
(C O), 1657 (aromatic C C str.),
1602 (C C str.).
3323 (NH str.), 2961 (aromatic C H),
2826 (aliphatic C H str.), 1750
(C O), 1598 (aromatic C C str.),
748 (C Cl str.), 499 (C Br str.).
332 (M+)
430/432 Isotopic
cluster
301 (30%) that is stablized by resonance and inturn
eliminates a hydrogen radical to generate cation rad-
ical VII at m/z 300 (48%).
This cation V further eliminates neutral moiety
C2O to give cation VIII. Cation III extruded neutral
HBr moiety to give cation IX at m/z 273 (64%) that
is stablized by resonance. Cation IX further elimi-
nates C4H2NO radical to afford cation radical XIII
at m/z 193 (22%). This cation radical corresponds
to 2-phenylindole species that is stablized by high
degree of resonance.
2-Phenylindolylcation radical XII eliminates
neutral NH moiety and undergoes ring expansion
to yield eight-membered cation radical XIV at m/z
178 (10%) that is stablized by resonance. Cation IX
eliminates O C NCH2 radical to afford cation rad-
ical XI at m/z 217 (80%) that readily loses CH radi-
cal to give ring expanded six-membered quinolinium
type cation XII at m/z 204 (38%). It inturn further
In the pathway B, cation radical I eliminates neu-
tral butylisocyanate and generates cation radical IV
at m/z 331/333 (25%). The cation radical IV shows
isotopic cluster due to the presence of bromo and
chloro groups. Cation IV by loss of CCl radical un-
dergoes rearrangement to give a six-membered ring
expanded cation VIII at m/z 284/286 (64%) that is
stablized by high degree of resonance (again the peak
ratio is 1:1). Cation VIII extruded neutral methane
and ammonia moieties to give a cation X at m/z
251/253 (13%). Cation II further eliminates neutral
C4H9N moiety to afford cation V at m/z 324 (30%)
that is stablized by resonance.
TABLE 3 Major Mass Fragments of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones
(4a)
(4e)
(4h)
Compounds
Fragment No.
m/z
Relative Intensity (%)
m/z
Relative Intensity (%)
m/z
Relative Intensity (%)
I
M+, 318
306
289
280
264
246
234
222
204
194
180
165
154
136
10.0
65.0
20.0
12.0
100.0
18.0
20.0
98.0
26.0
48.0
12.0
25.0
83.0
78.0
M+, 332
320
307
290
278
236
220
208
193
165
154
136
120
107
10
42.0
64.0
20.0
100.0
53.0
5.0
11.0
7.1
10.0
68.0
50.0
10.0
18.0
430/432
395/397
353/355
333
324
301
300
284/286
273
251/253
217
204
100
50
52
25
30
30
48
64
10
13
80
38
22
10
II
III
IV
V
VI
VII
VIII
IX
X
XI
XII
XIII
XIV
193
178

498 Pathak, Gupta, and Garg
SCHEME 3 Mass fragmentation pattern of 1-butyl-3-chloro-4-[2-(4-bromophenyl)-1H-indol-3-yl]-2-azetidinone (4h).

Synthesis, Spectral, and Antimicrobial Studies of 1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones 499
decomposes in two ways: either elimination of ben-
EXPERIMENTAL
zyne radical generates quinolinium ion XVI at m/z
128 (9%) or loses neutral cyclobutadien-1-yne moiety
to yield eight-membered ring expanded cation XV at
m/z 154 (49%).
All the melting points were determined in open cap-
illary tubes and are uncorrected. The IR spectra
(vmax in cm−1) were recorded on a Perkin Elmer-
557 grating infrared spectrophotometer in KBr pel-
lets. PMR spectra were recorded on Bruker spec-
trometer (200 MHz) using CDCl3 as a solvent. TMS
was used as internal standard (chemical shift in δ,
ppm). Mass spectra were recorded on Kratos 30
and 50 mass spectrometer. The purity of the com-
pounds was checked by TLC using silica gel-G as
adsorbent, UV light or iodine accomplished visual-
ization. 2-Arylindoles were prepared by the method
of Joshi et al. [18]. 2-Arylindol-3-carboxaldehydes
2 [15] and 3-butyliminomethyl-2-arylindole 3 [19]
were prepared by the literature method.
Antimicrobial Activity
All the synthesized compounds 4(a–l) were screened
for their antimicrobial activity against the gram-
negative bacteria Escherichia coli, gram-positive bac-
teria Klebisella pneumoniae, and fungi Aspergillus
flavus and Aspergillus niger at different concentra-
tions by disk diffusion method [7]. Streptomycin
and betadine are used as reference compounds
for evaluating antibacterial and antifungal activi-
ties respectively. Compounds 4g–l showed enhanced
antibacterial and antifungal activity at 200 ppm,
400 ppm, 800 ppm, and 1000 ppm due to the
presence of chlorine moiety in the ꢀ-lactam ring.
The results obtained are presented in Tables 4
and 5.
1-Butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-
azetidinones (4)
A mixture of 3-butyliminomethyl-2-arylindoles 3
(2 mmol) and triethylamine (4.2 mmol, 0.6 g) was
TABLE 4 Antibacterial Activity of 1-Butyl-3-substituted-4-[2-aryl-1H-indol-3-yl]-2-azetidinone (4a–l)
Mean Value of Area
of Inhibition in mm
1000 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
800 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
400 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
200 ppm IZ (IA)
Compounds
E. coli K. penumoniae E. coli K. penumoniae E. coli K. penumoniae E. coli
K. penumoniae
Streptomycin
4a
8.2
9.1
7.4
6.8
8.0
7.2
7.1
6.2
7.6
6.2
6.4
5.2
6.6
3.4
5.4
3.4
(1.10)
11.3
(1.31)
11.2
(1.36)
5.4
(.65)
6.8
(.82)
7.2
(.91)
6.4
(.86)
5.8
(.78)
4.9
(.66)
7.3
(.90)
9.8
(1.22)
10.1
(1.26)
4.2
(.52)
5.9
(.73)
6.8
(.87)
5.8
(.81)
4.2
(.59)
4.1
(.57)
6.9
(.81)
7.8
(1.02)
8.3
(1.09)
4.0
(.52)
4.7
(.81)
4.3
(.67)
3.3
(.51)
3.1
(.48)
5.3
(.51)
4.6
(.69)
6.3
(.95)
3.4
(.51)
4.0
(.62)
2.2
(.40)
2.4
(.44)
3.0
(.55)
4.3
4b
4c
4d
4e
4f
(.98)
8.2
(.97)
7.4
(.61)
6.2
(.82)
6.3
(.60)
3.8
(.79)
5.2
(.87)
16.4
(2.0)
18.1
(2.20)
15.2
(1.85)
14.3
(1.74)
11.5
(1.40)
10.8
(1.31)
(1.10)
11.6
(1.56)
11.9
(1.60)
13.2
(1.78)
10.8
(1.45)
9.6
(.85)
11.2
(1.40)
15.6
(1.95)
13.2
(1.65)
12.4
(1.55)
9.8
(1.04)
10.1
(1.42)
11.2
(1.57)
11.9
(1.67)
9.2
(1.29)
8.6
(1.21)
7.
(.81)
10.7
(1.40)
12.2
(1.60)
11.8
(1.55)
10.2
(1.34)
8.8
(.98)
8.4
(1.31)
9.3
(1.45)
9.8
(1.53)
7.4
(1.15)
7.6
(1.18)
6.4
(.57)
7.2
(1.09)
8.3
(1.25)
9.1
(1.37)
7.4
(1.12)
6.7
(1.01)
6.2
(.96)
7.6
(1.29)
7.6
(1.40)
8.2
(1.51)
5.3
(.98)
6.4
(1.18)
5.3
4g
4h
4I
4j
4k
4l
(1.29)
8.4
(1.13)
(1.22)
8.6
(1.07)
(1.15)
8.1
(1.06)
(1.07)
(1.00)
(.93)
(.98)
IZ = Inhibition area (zone) excluding diameter of disk.
Al (activity index) = Inhibition area of sample/inhibition area of standard.

500 Pathak, Gupta, and Garg
TABLE 5 Antifungal Activity of 1-Butyl-3-substituted-4-[2-aryl-1H-indol-3-yl]-2-azetidinone (4a–l)
Mean Value of Area
of Inhibition in mm
1000 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
800 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
400 ppm IZ (IA)
Mean Value of Area
of Inhibition in mm
200 ppm IZ (IA)
Compound
A. flavus
A. niger
A. flavus
A. niger
A. flavus
A. niger
A. flavus
A. niger
Betadiene
4a
7.2
7.0
8.1
7.6
6.8
6.2
8.0
7.2
6.6
6.0
7.6
5.6
5.9
5.1
7.3
5.2
(.97)
6.2
(.86)
6.9
(0.95)
5.6
(.77)
11.2
(1.55)
9.8
(1.36)
10.3
(1.43)
12.4
(1.72)
11.8
(1.63)
10.6
(1.47)
13.2
(1.83)
12.8
(1.77)
(.93)
6.7
(.82)
6.8
(.83)
7.2
(0.91)
6.0
(0.88)
5.8
(0.85)
5.2
(.76)
10.0
(1.47)
8.9
(.90)
6.4
(.80)
6.3
(.78)
6.9
(.86)
9.2
(1.15)
12.6
(1.57)
10.8
(1.35)
9.2
(1.15)
9.4
(1.17)
9.3
(0.90)
5.4
(0.81)
4.9
(.74)
4.6
(0.69)
9.2
(1.39)
7.8
(1.18)
8.8
(1.33)
9.1
(1.37)
10.4
(1.57)
9.8
(.73)
6.0
(.78)
5.9
(0.77)
6.1
(.80)
8.2
(0.07)
11.3
(1.48)
9.2
(1.22)
8.4
(1.10)
8.8
(1.15)
7.2
(1.86)
4.8
(0.81)
4.0
(0.67)
3.8
(.64)
6.9
(1.16)
7.0
(1.18)
7.8
(1.32)
8.1
(1.37)
8.5
(1.44)
7.5
(1.27)
9.1
(1.54)
8.2
(1.38)
(0.71)
5.4
(0.73)
4.2
(.57)
4.8
(.65)
6.5
(.89)
9.2
(1.26)
8.6
(1.17)
8.0
(1.09)
7.6
(1.04)
6.8
(.93)
9.4
(1.28)
8.2
(1.12)
4b
4c
4d
4e
4f
(.88)
10.6
(1.30)
13.0
(1.60)
11.4
(1.40)
10.9
(1.34)
10.5
(1.29)
9.9
(1.22)
12.1
(1.49)
11.6
(1.43)
(1.30)
9.6
4g
4h
4I
(1.41)
11.3
(1.66)
10.6
(1.55)
9.3
(1.36)
11.2
(1.64)
10.6
(1.55)
4j
(1.16)
11.6
(1.45)
10.3
(1.28)
(1.48)
8.4
(1.27)
10.1
(1.53)
(0.94)
10.6
(1.39)
9.2
4k
4l
(1.21)
IZ = Inhibition area (zone) excluding diameter of disk.
AI (activity index) = Inhibition area of sample/inhibition area of standard.
[2] Pawar, R. P.; Andurkar, N. M.; Vibhute, Y. B. J Indian
Chem Soc 1999, 76, 271.
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dissoloved in tetrahydrofuran (25 mL) and cooled
[2,20]. To this cooled solution, acetylchloride/
chloroacetyl chloride (2.4 mmol) was added slowly at
0◦C and the mixture was stirred for 24 h and then se-
taside for 48 h at room temperature. The precipitated
amine hydrochloride was filtered off, and tetrahydro-
furan was removed under vacuum. The residue was
poured into ice cold water and the resulting solid
mass was suction filtered, washed with water, dried,
and recrystallized from hexane.
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1995, 34B, 802.
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Richter, G.; Vegyeszeti, G. R. T. Hung Appl Aug 1962,
16, 13; (c) Richter, G.; Vegyeszeti, G. R. T. Chem Abstr
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ACKNOWLEDGMENT
We express our sincere gratitute to Dr. V. J. Ram
(Emeritus Scientist, Director, Medicinal Chemistry
Division, Central Drug Research Institute (CDRI),
Lucknow).
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