Synthesis of 2([methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3- thiazolan-4-ones and their Mannich bases

Article abstract of DOI:10.1080/10426500801967856

Isoxazolyl chloroacetamides (2) were obtained from 4-amino-3-methyl-5- styrylisoxazoles (1) on reaction with chloroacetyl chloride. Cyclocondensation of 2 with NH4SCN yielded 2([-methyl-5-(E)-2-aryl-1-ethenyl]-4-isoxazolylimino)- 1,3-thiazolan-4-ones(3).

Full text of DOI:10.1080/10426500801967856

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Phosphorus, Sulfur, and Silicon
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Synthesis of 2([Methyl-5-
[(E)-2-aryl-1-ethenyl]-4-
isoxazolyl]imino)-1,3-
thiazolan-4-ones and Their
Mannich Bases
E. Rajanarendar a , P. Ramesh a , E. Kalyan Rao a &
A. Siva Rami Reddy a
a Department of Chemistry , Kakatiya University ,
Warangal, India
Published online: 26 Sep 2008.
To cite this article: E. Rajanarendar , P. Ramesh , E. Kalyan Rao & A. Siva Rami
Reddy (2008) Synthesis of 2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-
thiazolan-4-ones and Their Mannich Bases, Phosphorus, Sulfur, and Silicon and the
Related Elements, 183:10, 2555-2564, DOI: 10.1080/10426500801967856
To link to this article: http://dx.doi.org/10.1080/10426500801967856
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Phosphorus, Sulfur, and Silicon, 183:2555–2564, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500801967856
Synthesis of 2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-
isoxazolyl]imino)-1,3-thiazolan-4-ones and Their
Mannich Bases
E. Rajanarendar, P. Ramesh, E. Kalyan Rao,
and A. Siva Rami Reddy
Department of Chemistry, Kakatiya University, Warangal, India
Isoxazolyl chloroacetamides (2) were obtained from 4-amino-3-methyl-5-styryl-
isoxazoles (1) on reaction with chloroacetyl chloride. Cyclocondensation of 2
with NH SCN yielded 2([-methyl-5-(E)-2-aryl-1-ethenyl]-4-isoxazolylimino)-1,3-
4
thiazolan-4-ones(3). Mannich reaction of 3 with formaldehyde and secondary
amines gave isoxazolyl thiazolidinone Mannich bases (4 and 5).
Keywords Isoxazolyl chloroacetamides; isoxazolyl thiazolidinones; Mannich bases
INTRODUCTION
Heterocycles are abundant in nature and are of great significance to
life; hence, they have attracted considerable attention in the design of
biologically active molecules and advanced organic materials. Among
a wide variety of heterocycles that have explored for developing phar-
maceutically important molecules, thiazolidinones constitute an im-
portant group due to their wide variety of biological activities such as
antitubercular,1 anticonvulsant,2 antifungal,3 antitumor,4 antimicro-
bial activities,5 and are also used in the treatment of arthritis.6 They
have also been utilized as hypolipidemics and hypocholesteremics.7
Thiazolidnone herbicides are the potent inhibitors of glucose incor-
poration into cell wall.8 Besides this, they are proved to be calcium
antagonists with both calcium overload inhibitors and antioxidant
activity.9
Mannich bases are reported to possess potent antibacterial, antifun-
gal, and anti-HIV activities.10 Similarly, isoxazole unit constitutes an
easily accessible nucleus that is present in a number of natural and
Received 2 December 2007; accepted 18 January 2008.
Address correspondence to E. Rajanarendar, Department of Chemistry, Kakatiya Uni-
versity, Warangal 506 009, India. E-mail: eligeti rajan@yahoo.co.in
2555

2556
E. Rajanarendar et al.
pharmacological compounds11 and displays a wide range of organic re-
activities and could be used as an effective means of preparing new
molecular scaffolds.12 Isoxazoles have been repeatedly shows as useful
synthons in organic synthesis.13
Our literature survey revealed that when one biodynamic hetero-
cyclic system was coupled with another, a molecule with enhanced
biological activity14,15 was produced. The chemistry of these linked
heterocycles has been a fascinating field of investigation in medici-
nal chemistry as they have been found to exhibit enhanced biological
profile.16 In view of these observations, and also as a sequel to our
search for biologically active nitrogen and sulfur heterocycles17 linked
to isoxazole rings, we planned to synthesize isoxazolyl thiazolidinone
Mannich bases, which may be useful as bioactive compounds.
RESULTS AND DISCUSSION
The starting material, 4-amino-3-methyl-5-styrylisoxazoles18 (1) were
secured by reduction of 3-methyl-4-nitro-5-styrylisoxazoles19 with stan-
nous chloride and conc. hydrochloric acid. The reaction of 4-amino-3-
methyl-5-styrylisoxazoles (1) with chloroacetyl chloride in the presence
of trimethyl amine in dry benzene furnished N-1-[3-methyl5-[(E)-2-
aryl-1-ethenyl]-4-isoxazolyl]-2-chloro acetamides (2). Compounds 2 on
cyclocondensation with ammonium thiocyanate in refluxing ethanol af-
forded 2-([3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl]imino)1,3-
thiazolan-4-ones (3). Compounds 2 displayed characteristic absorption
bands in the IR spectra around 1675 cm−1 and 3310 cm−1 due to
C
O and NH functional groups respectively. 1H NMR spectra of 2 ex-
hibited a singlet around δ4.2 due to CH2 proton and a broad singlet
around δ9.8 due to NH proton. The IR spectra of isoxazolyl thiazo-
lidinones (3) exhibited strong absorption bands around 3160 and 1650
cm−1 due to NH and C O functional groups respectively. 1H NMR
spectra of 3 recorded in CDCl3 confirmed the structural assignments.
The newly formed thiazolan-4-one ring CH2 protons resonated as a
sharp singlet around δ4.0, whereas NH proton signal appeared at δ9.0
The isoxazolyl thiazolidinones (3) on reaction with 37% formalde-
hyde and morpholine/piperidine-hydrochloride in ethanol yielded
Mannich bases viz., 2-([3-methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]
amino-3-morpholino methyl/ piperidino methyl)-1,3-thiazolan-4-ones
(4) and (5), respectively. Compounds (4) and (5) have shown strong ab-
sorption band in the IR spectra around 1720 cm−1 due to C O group.
The NH functional group absorption band which appeared at 3160 cm−1
in its precursor, was absent in compounds 4 and 5. Moreover, in the 1H

2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-thiazolan-4-ones 2557
SCHEME 1
NMR spectra of compounds 4 and 5 the signal at δ9.0, which is present
in its precursor (3) was not present. This indicates that the NH group
is involved in Mannich reaction in preference to methylene group.
In summary, we have prepared novel Mannich bases carrying isox-
azole and thiazolidinone moieties. In view of potential activity of these

2558
E. Rajanarendar et al.
TABLE I Data of Compounds (2a–e)* and (3a–e)*
Found (calcd.) %
M.p.
Mol. formula
(m.wt.)
Compd.
(◦C)
Yield (%)
60
C
H
N
S
2a
125
105
110
135
143
80
C14H13N2ClO2
(276)
60.79
4.75
10.08
—
(60.86) (4.71) (10.14)
2b
2c
2d
2e
3a
3b
3c
3d
3e
65
60
72
67
65
87
82
79
75
C15H15N2ClO2
(290)
62.01
(62.06) (5.17)
58.79 4.92
(58.82) (4.90)
54.23 3.91
(54.19) (3.87)
54.08 3.79
(54.19) (3.87)
60.15 4.37
5.09
9.58
(9.65)
9.21
(9.15)
9.01
(9.03)
9.08
(9.03)
14.01
—
—
C15H15N2ClO3
(306)
C
C
14H12N2Cl2O2
(310)
14H12N2Cl2O2
(310)
—
—
C
15H13N3O2S
(299)
10.62
(60.20) (4.34) (14.04) (10.70)
61.28 4.71 13.48 10.25
(61.34) (4.79) (13.41) (10.22)
72
C
16H15N3O2S
(313)
76
C
16H15N3O3S
(329)
58.39
(58.35) (4.55) (12.76)
54.11 3.51 12.55
(54.05) (3.60) (12.61)
54.01 3.69 12.57
(54.05) (3.60) (12.61)
4.59
12.67
9.69
(9.72)
9.69
(9.60)
9.62
107
112
C
15H12N3ClO2S
(333)
15H12N3ClO2S
(333)
C
(9.60)
∗Compounds 2a–e were recrystallized from aqueous methanol and 3a–e from
ethanol.
compounds, we predict that the newly synthesized Mannich bases may
be drug candidates, and the activity data will be published elsewhere.
EXPERIMENTAL
All the melting points were determined on a Cintex melting point ap-
paratus and are uncorrected. Analytical TLC was performed on Merck
precoated 60 F254 silica gel plates. Visualization was done by exposing
to Iodine vapor IR spectra (KBr pellet) were recorded on Perkin-Elmer
BX series FT-IR spectrophotometer. 1H NMR spectra were recorded
on a Varian Gemini 300 MHz spectrometer. Chemical shift values are
given in ppm (δ) with tetramethylsilane as internal standard. Mass
spectral measurements were carried out by EI method on a Jeol JMC-
300 spectrometer at 70 eV. Elemental analyses were performed on a
Carlo Erba 106 Perkin-Elmer model 240 analyzer.
The 4-Amino-3-methyl-5-styrylisoxazoles18 (1) were prepared ac-
cording to the literature procedure.

2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-thiazolan-4-ones 2559
N 1-[3-Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]-2-
chloroacetamides (2)
4-Amino-3-methyl-5-styrylisoxazole (1) (0.01 mol), chloroacetyl chlo-
ride (0.01 mol), and triethylamine (0.5 ml) were taken in dry benzene.
The contents were refluxed with stirring for 4–6 h. The precipitated
triethyl-amine hydrochloride was removed by filtration. The gummy
product obtained after the removal of solvent at ambient temperature
was triturated with methanol. Recrystallization of the product was ef-
fected from aqueous methanol (Tables I and III).
2-([3-Methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl]imino)1,3-
thiazolan-4-ones (3)
A mixture of compound 2 (0.01 mol) and NH4SCN (0.015 mol) were
taken in ethanol and refluxed on a water bath for 4–6 h. After com-
pletion of the reaction (monitored with TLC), the reaction mixture was
concentrated by rotary evaporator and the residue was washed thor-
oughly with cold water and it was purified by recrystallization from
ethanol (Tables I and III).
2-([3-Methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl]imino-3-
(morpholino methyl)-1,3-thiazolan-4-ones (4)
A solution of 0.5 ml of 37% formaldehyde and morpholine (0.01 mol)
were added dropwise with vigorous stirring to a suspension of isoxazolyl
thiazolidinones (3) (0.01 mol) in 20 ml of ethanol. The reaction mixture
was refluxed for 5–7 h. After completion of the reaction (monitored with
TLC), the reaction mixture was concentrated by rotary evaporator. The
crude solid obtained was purified by column chromatography to afford
isoxazolyl thiazolidinone morpholino Mannich bases (Tables II and III).
2-([3-Methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl]imino-3-
(piperidino methyl)-1,3-thiazolan-4-ones (5)
A mixture of compound 3 (0.01 mol), 1 ml of 37% formaldehyde and
piperidine hydrochloride (0.02 mol) were taken in ethanol (20 ml) and
the contents were refluxed for 3–5 h. After completion of the reac-
tion (monitored by TLC), the reaction mixture was allowed to cool and
poured into ice-cold water. The separated solid was purified by recrys-
tallization with aqueous methanol, to afford isoxazolyl thiazolidinone
piperidino Mannich bases (Tables II and III).

2560
E. Rajanarendar et al.
TABLE II Physical Data of Compounds (4a–e)* and (5a–e)*
Found (calcd.) %
M.p. Yield
Mol. formula
(m.wt.)
Compd.
(◦C)
(%)
C
H
N
S
4a
70
67
C20H22N4O3S
(398)
60.18
(60.30)
61.19
(61.16)
58.80
(58.87)
55.59
(55.55)
55.48
(55.55)
63.55
(63.63)
64.31
(64.39)
61.99
(61.97)
58.65
5.58
(5.52)
5.75
(5.82)
5.53
(5.60)
4.78
(4.86)
4.88
(4.86)
6.09
(6.06)
6.39
(6.34)
6.02
(6.10)
5.28
14.12
(14.07)
13.51
(13.59)
13.01
(13.08)
12.88
(12.96)
12.91
(12.96)
14.01
(14.04)
13.58
(13.65)
13.17
(13.14)
13.09
8.01
(8.04)
12.74
(12.69)
7.53
(7.47)
7.36
(7.40)
7.48
(7.40)
8.15
(8.08)
7.82
(7.80)
7.48
(7.51)
7.38
4b
4c
4d
4e
5a
5b
5c
5d
5e
68
65
81
84
79
75
69
76
81
85
72
C21H24N4O3S
(412)
C21H24N4O4S
(428)
98
C
C
20H21N4ClO3S
(432)
20H21N4ClO3S
(432)
105
180
171
165
195
201
C
21H24N4O2S
(396)
C22H26N4O2S
(410)
C22H26N4O2S
(426)
C
C
21H23N4ClO2S
(430)
21H23N4ClO2S
(430)
(58.60)
58.52
(58.60)
(5.34)
5.39
(5.34)
(13.02)
13.00
(13.02)
(7.44)
7.51
(7.44)
*Compounds 4a–e were purified by column chromatography and 5a–e were
recrystallized from aq. ethanol.
TABLE III Spectral Data of Compounds 2,3,4, and 5
IR (ν
cm−1
)
max
Mass spectra
Compd.
C
O
NH
1HNMR (δ ppm)
Mass spectra m/z (%) [M+H]+
2a
1692
1675
3320
2.3 (s, 3H, isoxazole-CH3),
4.2 (s, 2H, CH2), 6.8 (d, 1H,
CH CH), 7.0 (d, 1H, CH
CH), 7.1–7.5 (m, 5H,
277 (71)
Ar-H), and 9.9 (bs, 1H, NH)
2.3 (s, 3H, isoxazole- CH3),
2.4 (s, 3H, CH3), 4.1 (s, 2H,
CH2), 6.8 (d, 1H, CH CH),
7.0 (d, 1H, CH = CH),
2b
3290
291 (66)
7.1–7.5 (m, 4H, Ar-H), and
9.9 (bs, 1H, NH)

2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-thiazolan-4-ones 2561
TABLE III Spectral Data of Compounds 2,3,4, and 5 (Continued)
IR (ν
cm−1
)
max
Mass spectra
Compd.
C
O
NH
1HNMR (δ ppm)
Mass spectra m/z (%) [M+H]+
2c
1679
3295
2.2 (s, 3H, isoxazole- CH3),
3.7 (s, 3H, OCH3), 4.2 (s,
2H, CH2), 6.9 (d, 1H, CH
CH), 7.1 (d, 1H, CH
307 (62)
CH), 7.2–7.6 (m, 4H,
Ar-H), and 9.5 (bs, 1H, NH)
2.2 (s, 3H, isoxazole- CH3),
4.1 (s, 2H, CH2), 6.8 (d, 1H,
CH CH), 7.0 (d, 1H, CH
CH), 7.2–7.6 (m, 4H,
Ar-H), and 9.4 (bs, 1H, NH)
2.2 (s, 3H, isoxazole-CH3),
4.2 (s, 2H, CH2), 6.9 (d, 1H,
CH CH), 7.1 (d, 1H, CH
CH), 7.3–7.7 (m, 4H,
Ar-H), and 9.2 (bs, 1H, NH)
2.2 (s, 3H, isoxazole-CH3),
4.0 (s, 2H, CH2), 6.9 (d, 1H,
CH CH), 7.1–7.7 (m, 5H,
Ar-H & 1H, CH CH), and
9.0 (bs, 1H, NH)
2.2 (s, 3H, isoxazole-CH3),
2.4 (s, 3H, CH3), 3.9 (s, 2H,
CH2), 6.8 (d, 1H, CH CH),
7.0–7.5 (m, 4H, Ar-H & 1H,
CH CH), and 8.2 (bs, 1H,
NH)
2d
2e
3a
3b
1681
1682
1672
1665
3326
3310
3280
3210
311 (65)
311 (60)
300 (69)
314 (42)
3c
1685
3310
2.3 (s, 3H, isoxazole-CH3),
3.8 (s, 3H, OCH3), 4.0 (s,
2H, CH2), 6.9 (d, 1H, CH
CH), 7.1–7.6 (m, 4H, Ar-H
& 1H, CH CH), and 9.9
(bs, 1H, NH)
330 (52)
3d
3e
1674
1660
3250
3190
2.2 (s, 3H, isoxazole-CH3),
4.1 (s, 2H, CH2), 6.9 (d, 1H,
CH CH), 7.1–7.6 (m, 4H,
Ar-H & 1H, CH CH), and
9.3 (bs, 1H, NH)
2.3 (s, 3H, isoxazole-CH3),
4.1 (s, 2H, CH2), 6.8 (d, 1H,
CH CH), 7.0–7.5 (m, 4H,
Ar-H & 1H, CH CH), and
8.6 (bs, 1H, NH)
334 (46)
334 (73)
(Continued on next page)

2562
E. Rajanarendar et al.
TABLE III Spectral Data of Compounds 2,3,4, and 5 (Continued)
IR (ν
cm−1
)
max
Mass spectra
Compd.
C
O
NH
—
1HNMR (δ ppm)
Mass spectra m/z (%) [M+H]+
4a
1716
2.2 (s, 3H, isoxazole-CH3),
2.7 (t, 4H, CH2 NCH2), 3.6
(t, 4H, CH2-OCH2), 3.9 (s,
2H, CH2), 4.7 (s, 2H,
399 (42)
NCH2N), 6.8(d, 1H, CH
CH), 7.0 (d, 1H, CH CH),
and 7.4–7.8 (m, 5H, Ar-H)
2.3 (s, 3H, isoxazole-CH3),
2.5 (s, 3H, CH3), 2.8 (t, 4H,
CH2NCH2), 3.7 (t, 4H,
CH2OCH2), 3.9 (s, 2H,
CH2), 4.8 (s, 2H, NCH2N),
6.7 (d, 1H, CH CH), 7.0
(d, 1H, CH CH), and
4b
4c
1720
—
—
413 (33)
7.3–7.8 (m, 4H, Ar-H)
1729
2.3 (s, 3H, isoxazole-CH3),
2.8 (t, 4H, CH2NCH2), 3.7
(t, 4H, CH2OCH2), 3.9 (s,
3H, OCH3), 4.1 (s, 2H,
429 (53)
CH2), 4.9 (s, 2H, NCH2N),
6.8 (d, 1H, CH CH), 7.1
(d, 1H, CH CH), and
7.2–7.7 (m, 4H, Ar-H)
4d
4e
5a
1721
1725
1718
—
—
—
2.2 (s, 3H, isoxazole-CH3),
2.7 (t, 4H, CH2NCH2), 3.7
(t, 4H, CH2OCH2), 4.1 (s,
2H, CH2), 4.8 (s, 2H,
NCH2N), 6.7 (d, 1H, CH
CH), 7.0 (d, 1H, CH CH),
and 7.2–7.6 (m, 4H, Ar-H)
2.1 (s, 3H, isoxazole-CH3),
2.7 (t, 4H, CH2NCH2), 3.8
(t, 4H, CH2OCH2), 4.0 (s,
2H, CH2), 4.7 (s, 2H,
NCH2N), 6.8 (d, 1H, CH
CH), 7.1 (d, 1H, CH CH),
and 7.3–7.7 (m, 4H, Ar-H)
1.6 (m, 6H, (CH2)3), 2.2 (s,
3H, isoxazole-CH3), 2.8 (t,
4H, CH2NCH2), 4.0 (s, 2H,
CH2), 4.6 (s, 2H, NCH2N),
and 6.9–7.8 (m, 5H, Ar-H &
2H, CH CH)
433 (64)
433 (42)
397 (49)

2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-thiazolan-4-ones 2563
TABLE III Spectral Data of Compounds 2,3,4, and 5 (Continued)
IR (ν
cm−1
)
max
Mass spectra
Compd.
C
O
NH
—
1HNMR (δ ppm)
Mass spectra m/z (%) [M+H]+
5b
1715
1.7 (m, 6H, (CH2)3), 2.1 (s,
3H, isoxazole-CH3), 2.4 (s,
3H, CH3), 2.9 (t, 4H,
411 (54)
CH2NCH2), 3.9 (s, 2H,
CH2), 4.7 (s, 2H, NCH2N),
and 6.9–7.7 (m, 4H, Ar-H &
2H, CH CH)
5c
1724
—
1.6 (m, 6H, (CH2)3), 2.3 (s,
3H, isoxazole-CH3), 2.8 (t,
4H, CH2NCH2), 3.7 (s, 3H,
OCH3), 4.1 (s, 2H, CH2),
4.9 (s, 2H, NCH2N), and
6.8–7.6 (m, 4H, Ar-H & 2H,
CH CH)
427 (45)
5d
5e
1722
1720
—
—
1.7 (m, 6H, (CH2)3), 2.2 (s,
3H, isoxazole-CH3), 2.6 (t,
4H, CH2NCH2), 3.7 (s, 2H,
CH2), 4.7 (s, 2H, NCH2N),
and 6.9–7.6 (m, 4H, Ar-H &
2H, CH CH)
1.5 (m, 6H, (CH2)3), 2.3 (s,
3H, isoxazole-CH3), 2.7 (t,
4H, CH2NCH2), 3.8 (s, 2H,
CH2), 4.6 (s, 2H, NCH2N),
and 7.0–7.7 (m, 4H, Ar-H &
2H, CH CH)
431 (60)
431 (69)
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