Ultrasound-accelerated synthesis of some bis-compounds and their biological evaluation

Article abstract of DOI:10.1002/jhet.53

A new series of bis-1, 5-[2′H, 3'H-dihydro-4′(substituted phenyl)-1', 5′-benzothiazipin-2'-oxy]-3, 3- dimethyl-1, 4-cyclohexadiene 3 and bis-1, 5-[-2′, 3′, 4′, 5′-teterahydro-2′- (substitutedphenyl)-4′-oxo- thiophen-3′-carboxylate]-3, 3-dimethyl-1, 4-cycl

Full text of DOI:10.1002/jhet.53

March 2009
Ultrasound-Accelerated Synthesis of Some Bis-Compounds and
Their Biological Evaluation
303
Vijay V. Dabholkar* and Faisal Y. Ansari
Organic Research Laboratory, Department of Chemistry, K.C. College, Churchgate,
Mumbai 400020, India
*E-mail: vijaydabholkar@gmail.com
Received May 2, 2008
DOI 10.1002/jhet.53
Published online 20 March 2009 in Wiley InterScience (www.interscience.wiley.com).
A new series of bis-1,5-[20H,30H-dihydro-40(substituted phenyl)-10,50-benzothiazipin-20-oxy]-3,3-
dimethyl-1,4-cyclohexadiene
3
and bis-1,5-[-20,30,40,50-teterahydro-20-(substitutedphenyl)-40-oxo-
thiophen-30-carboxylate]-3,3-dimethyl-1,4-cyclohexadiene 4 have been synthesized by reacting 1,3-bis-
[substituted cinnamate]-3,3-dimethyl-1,4-cyclohexadiene 2 with 2-aminothiophenol and thiogylcolic
acid, respectively, through an environmentally benign procedure. The title compounds have been eval-
uated for their antimicrobial activities. Reaction under ultrasound irradiation resulted in enhancement of
yields and reaction rates. Structures of the synthesized compounds have been elucidated on the basis of
the elemental analysis and spectral data.
J. Heterocyclic Chem., 46, 303 (2009).
INTRODUCTION
pertensive [26], antidementia [27], antibacterial, and
anti-fungal activities [28–30]. The biodynamic nature
of benzothiazepines derivatives led to the current
synthesis of 1,5-benzothiazepines having various sub-
stituents, which may prove to be of medical signifi-
cance. Similarly, thiophenes derivatives are also well
known for diverse biological activities and play a key
role as anti-inflammatory [31,32], anti-protozoa [33],
antitumor agents [34], and alternate substrate inhibitors
of cholesterol eastrase [35]. In recent years, attention
has been increasingly paid to the synthesis of bis-hetero-
cyclic compounds, which exhibit various biological
activities [36–45]. The wide range of therapeutic
value of the above ring system prompted us to syn-
thesize several new bis-1,5-[substituted cinnamate]-3,
3-dimethyl-1,4-cyclohexadiene 2 and its utility as a
building block in the synthesis of several new bis-1,
The use of ultrasound irradiation for activating vari-
ous reactions is well documented in the literature such
as synthesis of azoles and diazenes [1], Reformatsky
reaction [2], oxidation of substrates like hydroquinones
[3], conversion of nitro compounds to carbamates [4],
pinacol coupling [5], Ullmann condensation [6] etc.
The advantages of ultrasound-assisted chemical reac-
tions include higher yields, shorter reaction times, and
milder reaction conditions when compared with classical
methods [7–11]. The effect of ultrasound has mostly
been shown by increasing the yields of reactions and in
some cases, changing the ratio of products formed. The
most important effects of ultrasound arise from acoustic
cavitation; formation, growth, and implosive collapse of
bubbles in the liquid by passing ultrasonic waves
through this medium [12,13]. The implosive collapse of
the bubble generates localized hot spots through adia-
batic compression or shock wave formation within the
gas phase of the collapsing bubble. These bubbles create
pressures of hundreds of atmospheres and temperature
of thousands of degrees within the cavities during their
collapse [14,15]. In all of these reactions, it was found
that ultrasound accelerates the reactions [16–22].
5-[20H,30H-dihydro-40(substituted
phenyl)-10,50-benzo-
thiazepin-20-oxy]-3,3-dimethyl-1,4-cyclohexadiene
3
and bis-1,5-[-20,30,40,50-teterahydro-20-(substitutedphenyl)-
40-oxothiophen-30-carboxylate]-3,3-dimethyl-1,4-cyclo-
hexadiene 4 compounds (Scheme 1). The structures of
the products were confirmed by elemental analysis,
1
IR, H, 13C NMR, and MS spectral analysis. The anti-
microbial activities of the newly synthesized com-
pounds were also investigated.
Benzothiazepine derivatives possess potential anti-
ulcer [23], analgesic [24], vaso-depressant [25], anti hy-
C
V
2009 HeteroCorporation

304
V. V. Dabholkar and F. Y. Ansari
Vol 46
Scheme 1
RESULTS AND DISCUSSION
(ACASA) also confirmed. In 13C NMR spectra, the sig-
nal at 65 ppm was observed because of >CHASA and
70 (>CASAbenzothiazepine ring).
The reaction sequences leading to the different bis-
heterocyclic ring is outlined in Scheme 1. The reaction
of 3,3-dimethyl-1,5-dihydroxy-1,4-cyclohexadiene with
acetic anhydride yielded bis-1,5-[acetoxy]-3,3-dimethyl-
1,4-cyclohexadiene which was converted into bis-1,5-
[substituted cinnamate]-3,3-dimethyl-1,4-cyclohexadiene
2, on treatment with substituted aromatic aldehydes.
Formation of compound 2 was evidenced by the appear-
ance of a signal at 7.8 ppm (a,b unsaturated carbonyl)
Similarly, the bis-1,5-[substituted cinnamate]-3,3-di-
methyl-1,4-cyclohexadiene 2 on treatment with thio-
glycolic acid underwent cyclization to the bis-1,5-
[20,30,40,50-teterahydro-20-(substitutedphenyl)-40-oxothio-
phen-30-carboxylate]-3,3-dimethyl-1,4-cyclohexadiene 4
(Scheme 1). The spectral data are in agreement with the
proposed structures. The IR spectrum of 4 showed CAS
1
stretching bands at 1340–1350 cmꢀ1 and its H NMR
1
in the H NMR spectra and in IR spectra band because
of carbonyl at 1634 cmꢀ1. In the 13C NMR spectra, the
signal 188.24 ppm was observed due to O¼¼C< in
compound 2. The reaction of 2-aminothiophenol with
compounds having a,b unsaturated in conjugation with
carbonyl system in acidic media afforded bis-1,5-
[20H,30H-dihydro-40(substitutedphenyl)-10,50-benzothiazi-
pin-20-oxy]-3,3-dimethyl-1,4-cyclohexadiene 3. In 1H
NMR spectra of compound 3, the signal at 3.74 was
observed due to ANHA, 6.0 due to CAH and at 7.35
due to CAH and in the IR spectra of bis-benzothiaze-
pine 3, the band at 3070 (ANAHA) and 1432 cmꢀ1
spectrum the chemical shifts due to CH2 of ring was
observed at 3.42 ppm. Appearance of two C¼¼O at
196.66 and 199.23 ppm in 13C NMR confirmed the for-
mation of 4. Keeping in view the advantages of ultra-
sound irradiation technique, the reaction was also car-
ried out under sonication condition. The formation of
compounds 2, 3, and 4 was completed in 15 to 25 min
under sonication condition when compared with conven-
tional method, which took 4 to 5 h. The compounds
obtained by both the routes were found identical as they
showed same melting point and similar spectral data.
Journal of Heterocyclic Chemistry
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Ultrasound-Accelerated Synthesis of Some Bis-Compounds
and Their Biological Evaluation
305
Table 1
Physical and analytical data of compounds 2, 3, and 4.
Analysis % Calcd./Found
Yield
(%) Conv
Molecular
formula
Compound
R
m.p (ꢁC)
200–202
Yield (%)
82
C
H
N
S
2a
H
58
59
59
58
67
65
60
58
55
C26H24O4
C28H28O6
78.21
77.87
73.04
72.84
72.22
72.14
73.22
73.08
70.15
69.41
69.45
69.32
69.49
69.21
63.15
62.94
65.45
65.23
6.01
5.91
6.08
5.85
5.55
5.24
5.76
5.47
5.84
5.68
5.46
5.34
5.40
5.23
5.26
5.11
5.09
4.96
–
–
–
–
–
–
–
–
2b
2c
3a
3b
3c
4a
4b
4c
OCH3
OH
215–217
198–199
70–72
87
81
72
79
75
77
70
76
–
–
C26H24O6
–
–
H
C38H34N2O2S2
C40H38N2O4S2
C38H34N2O4S2
C30H28O6S2
C32H32O8S2
C30H28O8S2
4.74
4.59
4.30
4.12
4.50
4.38
–
10.84
10.68
9.84
OCH3
OH
73–76
9.73
95–97
10.28
10.11
12.35
12.21
10.58
10.32
11.63
11.32
H
165–167
148–149
158–160
–
OCH3
OH
–
–
–
–
The comparative data of the compounds have been
listed in Table 1.
the compounds showed less activity toward gram-nega-
tive bacteria E coli and P aeruginosa. The results of
antibacterial screening studies are reported in Table 2.
Antibacterial activity. All the newly synthesized
compounds were initially screened for their in vitro anti-
bacterial activities against the gram-positive S aureus, C
diphtheriae, and S cerevisiae, the gram-negative E coli
and P aeruginosa by disc diffusion method [46].The
compounds were tested at a concentration of 100 lg/
mL. The zone of inhibition was measured in mm and
was compared with the reference standard antibiotics
namely ampicillin trihydrates drugs 50 lg/mL. Com-
pounds displayed good activity toward the gram-positive
bacteria S aureus, C diphtheriae, and S cerevisiae, but
CONCLUSIONS
In conclusion, the ultrasound irradiation for synthesis
of the title compound offers significant reduction in the
reaction time, operation simplicity, cleaner reaction,
easy work-up, and improved yields. The procedure
clearly highlights the advantages of ultrasound. The syn-
thesized compounds also displayed noteworthy convinc-
ing antibacterial activity against gram-positive bacteria S
aureus, C diphtheriae, and S cerevisiae.
Table 2
Antibacterial activity of compounds 2, 3, and 4.
Zone of inhibition (mm)a
Gram positive
Gram negative
P. aerugnosa
Concentration
(lg/mL)
Compound
S. aureus
S. cervesiae
C.diphtheria
E. coli
2a
2b
2c
3a
3b
3c
4a
100
100
100
100
100
100
100
100
100
50
16
17
18
19
21
22
21
20
19
26
00
18
19
19
18
21
20
19
17
19
23
00
17
18
17
18
19
17
18
21
22
28
00
08
09
09
08
09
09
11
09
11
24
00
09
08
10
09
11
10
10
11
10
21
00
4b
4c
Ampicilin trihydrate
DMSO
–
a Diameter of the hole was 6 mm.
Journal of Heterocyclic Chemistry
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306
V. V. Dabholkar and F. Y. Ansari
Vol 46
EXPERIMENTAL
8-H, aromatic proton). 13C NMR: 26.86 (CH3)2, 37.64 (CH2),
40.76 (OCH3), 72.89 (tetrahedral carbon) and 113–115.35
(4xC¼¼C), 125.89–131.83 (ArAC), 189.98 (C¼¼O), MS: m/z
432 (mþ2). Anal. Calcd. for C26H24O6: C, 72.22; H, 5.67.
Found: C, 72.14; H, 5.63.
General preparation of bis-1,5-[20H,30H-dihydro-40(sub-
stitutedphenyl)-10,50-benzothiazipin-20-oxy]-3,3-dimethyl-1,
4-cyclohexadiene (3a-c).
Method A (ultrasound method). A mixture of (0.01 mol) 2,
2.14 mL (0.02 mol) 2-aminothiophenol and 1 mL acetic acid in 10
mL of ethanol was subjected to ultrasound irradiation for 24 min.
The reaction mixture was poured on crushed ice. The solid sepa-
rated, filtered, washed with water, and recrystallized from ethanol.
Method B (conventional method). A solution of (0.01 mol)
2, 2.14 mL (0.02 mol) 2-aminothiophenol and 1 mL acetic
acid in 10 mL of ethanol was reflux on water bath for 3 h then
poured on to ice, the product was isolated in a similar manner
as described in the above method.
Melting points of all synthesized compounds were deter-
mined in open capillary tubes on an electrothermal apparatus
and are uncorrected. The purity of the compounds was moni-
tored by TLC on silica gel coated aluminium plates (Merck)
as adsorbent and UV light as visualizing agent; IR spectra (po-
tassium bromide in cmꢀ1) were recorded on a Perkin-Elmer
spectrophotometer in the range of 4000–400 cmꢀ1 1H NMR
.
spectra were recorded on Varian 500 MHz NMR spectropho-
tometer using deuteriochloroform as solvent and trimethylsi-
lane as an internal standard (chemical shifts in d ppm) and MS
spectra were taken on a Jeol sx-102/PA-6000 (EI) spectrome-
ter. C, H, N estimation was recorded on Carlo Erba 1108
(CHN) Elemental Analyzer. Experiment under ultrasound irra-
diation is carried out in probe sonicator manufactured by
Dakshin.
General preparation of bis-1,5-[substituted cinnamate]-
3,3-dimethyl-1,4-cyclohexadiene (2a-c).
Bis-1,5-[20H,30H-dihydro-40phenyl-10,50-benzothiazipin-20-
oxy]-3,3-dimethyl-1,4-cyclohexadiene (3a). This compound
was obtained as light yellow crystal, mp 70–72ꢁC; IR (potas-
Method A (ultrasound method). A mixture of (0.02 mol)
substituted aromatic aldehyde, (0.01 mol) 1, 2 mL (0.02 mol)
of piperidine in 15 mL of ethanol were exposed to ultrasound
irradiation for 15 min. On completion of the reaction (monitor-
ing on TLC), the mixture was poured on crushed ice. The
product that precipitated out was collected by filtration,
washed with water, and recrystallized from ethanol.
Method B (conventional method). A solution of (0.02 mol)
substitute aromatic aldehydes, (0.01 mol) 1, 2 mL (0.02 mol)
piperidine in 15 mL of ethanol were refluxed on water bath
for 4 h. The reaction was monitored by TLC, and after com-
pletion of the reaction, the contents were poured on crushed
ice. The solid obtained was collected by filtration, washed
with water, and recrystallized from ethanol to obtain com-
pound 2(a-c).
sium bromide): C¼¼C 1632, CASAC 1456 cmꢀ1
,
1H NMR
(deuterio-chloroform): d 0.96 (s, 6-H, 2xCH3), 2.44 (s, 2-H,
CH2), 3.62 (s, 2-H, NH), 4.25 (s, 2-H, CH), 6.56 (d, 2-H,
C2AH), 7.24 (d, 2-H, C3AH), 6.56–8.06 (m, 18-H, Aromatic
protons). 13C NMR: 27.24 (2xCH3), 32.45 (CH2), 65.45
(C2AH), 72.21 (C3AH), 73.54 (tetrahedral carbon) and
108.15–136.748 (C¼¼C and ArAC), MS: m/z 616 (mþ2). Anal.
Calcd. for C38H34N2O2S2: C, 73.22; H, 5.76; N,4.74; S, 10.84
Found: C, 73.08;H, 5.47; N, 4.59; S, 10.68.
Bis-1,5-[20H,30H-dihydro-40(400-methoxyphenyl)-10,50-benzothia-
zipin-20-oxy]-3,3-dimethyl-1,4-cyclohexadiene (3b). This com-
pound was obtained as greenish yellow crystal, mp 73–76ꢁC;
1
IR (potassium bromide): C¼¼C 1625, CASAC 1443 cmꢀ1, H
Bis-1,5-[cinnamate]-3,3-dimethyl-1,4-cyclohexadiene (2a). This
compound was obtained as white crystal, mp 200–202ꢁC; IR
NMR (deuteriochloroform): d 0.99 (s, 6-H, 2xCH3), 2.44 (s, 2-
H, CH2), 3.55 (s, 2-H, NH), 3.85 (s, 6-H, OCH3), 4.32 (s, 2-H,
CH), 6.43 (d, 2-H, C2AH), 7.37 (d, 2-H, C3AH), 6.96–8.03
(m, 16-H, Aromatic protrons). 13C NMR: 26.31 (2xCH3),
32.89 (CH2), 39.32 (OCH3), 65.52 (C2AH), 72.63 (C3AH),
73.76 (tetrahedral carbon), 108–136.31 (C¼¼C and ArAC),
MS: m/z 676 (mþ2). Anal. Calcd. for C40H38N2O4S2: C, 70.15;
H, 5.84; N,4.30; S, 9.84. Found: C, 69.41; H, 5.68; N, 4.12; S,
9.73.
(potassium bromide): CO 1645, C¼¼C 1625 cmꢀ1
;
1H NMR
(deuteriochloroform): d 0.96 (s, 6-H, 2xCH3), 2.44 (s, 2-H,
CH2), 4.69 (s, 2-H, CH), 7.82 (s, 4H, a, b unsaturated car-
bonyl), 6.98–8.02 (m, 10-H, aromatic protons). 13C NMR:
27.28 (CH3)2, 37.33 (CH2), 73.08 (tetrahedral carbon) and
108.21–115.32 (4xC¼¼C), 125.69–131.56 (ArAC), 188.42
(C¼¼O), MS: m/z 402 (mþ2). Anal. Calcd. for C26H24O4: C,
78.21; H, 6.01. Found: C, 77.87; H, 5.91.
Bis-1,5-[20H,30H-dihydro-40(400-hydroxyphenyl)-10,50-benzothia-
zipin-20-oxy]-3,3-dimethyl-1,4-cyclohexadiene (3c). This com-
pound was obtained as colorless crystal, mp 95–97ꢁC; IR (po-
Bis-1,5-[400-methoxycinnamate]-3,3-dimethyl-1,4-cyclohex-
adiene (2b). This compound was obtained as light green crys-
tal, mp 215–217ꢁC; IR (potassium bromide): CO 1652, C¼¼C
tassium bromide): OH 3448, C¼¼C 1636, CASAC 1421 cmꢀ1
,
1620 cmꢀ1
;
1H NMR (deuteriochloroform): d 1.07 (s, 6-H,
1H NMR (deuteriochloroform): d 1.02 (s, 6-H, 2xCH3), 2.34
(s, 2-H, CH2), 3.57 (s, 2-H, NH), 4.32 (s, 2-H, CH), 4.73 (s, 1-
H, OH), 6.38 (d, 2-H, C2AH), 7.63 (d, 2-H, C3AH), 6.73–7.83
(m, 16-H, Aromatic proton). 13C NMR: 27.45 (2xCH3), 31.67
(CH2), 65.68 (C2AH), 73.54 (C3AH), 73.76 (tetrahedral car-
bon), 105.45–137.76 (C¼¼C and ArAC), MS: m/z 648 (mþ2).
Anal. Calcd. for C38H34N2O4S2: C, 69.45; H, 5.49; N,4.50; S,
10.28. Found: C, 69.32; H, 5.34; N, 4.38; S, 10.11.
2xCH3), 2.25 (s, 2-H, CH2), 3.73 (s, 6-H, OCH3), 4.75 (s, 2-H,
CH), 7.89 (s, 4-H, a, b unsaturated carbonyl), 6.88–7.89 (m,
8-H, aromatic proton). 13C NMR: 26.32 (CH3)2, 37.89 (CH2),
41.21 (OCH3), 73.87 (tetrahedral carbon) and 111.32–114.45
(4xC¼¼C), 126.34–132.43 (ArAC), 189.09 (C¼¼O), MS: m/z
462 (mþ2). Anal. Calcd. for C28H28O6: C, 73.04; H, 6.08.
Found: C, 72.84; H, 5.85.
Bis-1,5-[400-hydroxycinnamate]-3,3-dimethyl-1,4-cyclohex-
adiene (2c). This compound was obtained as yellow crystal,
mp 198–199ꢁC; IR (potassium bromide): OH 3421, CO 1631,
General preparation of bis-1,5-[-20,30,40,50-teterahydro-20-
(substitutedphenyl)-40-oxo-thiophen-30-carboxylate]-3,3-di-
methyl-1,4-cyclohexadiene (4a-c).
Method A (ultrasound method). A mixture of (0.01 mol) 2,
1.38 mL (0.02 mol) thiogylcolic acid, 1 g zinc dust in 10 mL
of dioxane were subjected to ultrasound irradiation for 20 min.
1
C¼¼C 1610 cmꢀ1, H NMR (deuteriochloroform): d 0.98 (s, 6-
H, 2xCH3), 2.34 (s, 2-H, CH2), 4.56 (s, H, OH), 4.67 (s, 2-H,
CH), 7.76 (s, 4-H, a, b unsaturated carbonyl), 6.95–7.79 (m,
Journal of Heterocyclic Chemistry
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March 2009
Ultrasound-Accelerated Synthesis of Some Bis-Compounds
and Their Biological Evaluation
307
[2] Ross, N. A. R.; Bartsch, A. J Heterocycl Chem 2001, 38,
After completion of the reaction, as monitored by TLC,
the mixture was poured into ice-cold water. The solid
obtained was collected by filtration and recrystallized from
alcohol. The characteristic data of the compound are given in
Table 2.
1255.
[3] Singh, V.; Sapehivia, L.; Kad, G. L. Synthesis 2003, 2, 198.
[4] Chandrashekhar, S.; Jagadeshwar, V. Synlett 2001, 5,
771.
[5] Ji-Tai, L.; Yan-Jiang, B.; Hon-Jun, Z.; Tong-Shuang, L.
Method B (conventional method). A mixture of (0.01 mol)
2, 1.38 mL (0.02 mol) thiogylcolic acid and 1 g zinc dust in
10 mL of ethanol were heated under mild condition for 4.5 h.
The product was isolated in a similar manner as described above.
Bis-1,5-[-20,30,40,50-teterahydro-20-(phenyl)-40-oxo-thiophen-30-
carboxylate]-3,3-dimethyl-1,4-cyclohexadiene (4a). This com-
pound was obtained as light cream crystal, mp 165–167ꢁC; IR
Synth Commun 2002, 32, 547.
[6] Robin, M.; Pique, V.; Faure, R. J Heterocycl Chem 2002,
39, 1083.
[7] Suslick, K. S.; Goodale, J. W.; Schubert, P. F.; Wang, H. H.
J Am Chem Soc 1983, 105, 5781.
[8] Mason, T. J.; Lorimer, J. P. Chem Soc Rev 1987, 16,
239.
1
(potassium bromide): CO 1628, CASAC 1408 cmꢀ1. H NMR
[9] Suslick, K. S. Ultrasound Its Chemical, Physical, and Bio-
logical Effects;Verlag Chemie: New York, 1988.
[10] Einhorn, C.; Einhorn, J.; Luche, J. L. Synthesis 1989,
787.
(deuteriochloroform): d 0.97 (s, 6-H, 2xCH3), 2.44 (s, 2-H,
CH2), 3.21 (s, 2-H, C02AH), 3.46 (s, 4-H,2XCH2), 3.90 (s, 2-
H, C03AH), 4.69 (s, 2-H, CH), 7.19–8.02 (m, 10-H, Aromatic
13
proton). C NMR: 27.29 (2xCH3), 29.28 (C02), 32.18 (CH2),
[11] Reyman, D.; Pardo, A.; Poyato, J. M. L.; Rodriguez, J. G.
J Photochem Photobiol A Chem 1996, 98, 39.
[12] Nebois, P.; Bouaziz, Z.; Fillion, H.; Moeini, L.; Piquer, M.
J. A.; Luche, J. L.; Reira, A.; Pericas, M. A. Ultrasonics Sonochem
1996, 3, 7.
42.21 (C03), 50.71(CH2AC05), 73.21 (tetrahedral carbon),
109.10–115.5 (2xC¼¼C), 128.21–131.56 (ArAC), 196.44
(C¼¼O), 210.21 (C¼¼O). MS: m/z 520 (mþ2). Anal. Calcd. for
C30H28O6S2: C, 69.49; H, 5.40; S, 12.35. Found: C, 69.21; H,
5.23; S, 12.21.
´ ´
´
[13] Gaplovsky, A.; Donovalova, J.; Toma, S.; Kubinec, R.
Bis-1,5-[-20,30,40,50-teterahydro-20-(400-methoxyphenyl)-40-oxothio-
Ultrasonics Sonochem 1997, 4, 109.
phen-30-carboxylate]-3,3-dimethyl-1,4-cyclohexadiene
(4b). This
compound was obtained as dark green crystal, mp 148–149ꢁC;
IR (potassium bromide): CO 1610, CASAC 1443 cmꢀ1 1H
[14] Compton, R. G.; Akkermans, R. P.; Coles, B. A.; Marken,
F. Ultrasonics Sonochem 1997, 4, 223.
´
´
´
[15] Gaplovsky, A.; Donovalova, J.; Toma, S.; Kubinec, R. J
Photochem Photobio A Chem 1998, 115, 13.
[16] Shirgaonkar, I. Z.; Pandit, A. B. Ultrasonics Sonochem
1998, 5, 53.
.
NMR (deuteriochloroform): d 0.96 (s, 6-H, 2xCH3), 2.36 (s, 2-
H, CH2), 3.21 (s, 2-H, C02AH), 3.46 (s, 4-H, 2xCH2), 3.83 (s,
2-H, C03AH), 3.94 (s, 6-H, OCH3), 4.43 (s, 2-H, CH), 6.81–
7.83 (m, 8-H, Aromatic proton). 13C NMR: 27.32 (2xCH3),
29.43 (C02), 31.67 (CH2), 39.34 (OCH3), 41.54 (C03),
52.56 (CH2AC05), 73.02 (tetrahedral carbon), 110.98–116.12
(2xC¼¼C), 116.32–133.34 (ArAC), 198.07 (C¼¼O), 209.87
(C¼¼O). MS: m/z 610 (mþ2). Anal. Calcd. for C32H32O6S2: C,
63.15; H, 5.26; S, 10.58. Found: C, 62.94; H, 5.11; S, 10.32.
Bis-1,5-[-20,30,40,50-teterahydro-20-(400-hydroxyphenyl)-40-oxo-
thiophen-30-carboxylate]-3,3-dimethyl-1,4-cyclohexadiene (4c). This
compound was obtained as colorless crystal, mp 158–160ꢁC;
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IR (potassium bromide): CO 1615, CASAC 1448 cmꢀ1
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1H NMR (deuteriochloroform): d 9.86 (s, 6-H, 2xCH3), 2.21
(s, 2-H, CH2), 3.28 (s, 2-H, C02AH), 3.38 (s, 4-H, 2xCH2),
3.97 (s, 2-H, C03AH), 4.51 (s, 2-H, CH), 4.75 (s, 2-H, OH),
7.08–8.16 (m, 8-H, Aromatic proton). 13C NMR: 27.12
(2xCH3), 29.87 (C02), 32.54 (CH2), 41.84 (C03),
52.93 (CH2AC05), 73.12 (tetrahedral carbon), 109.12–116.23
(2xC¼¼C), 116.34–136.65 (ArAC), 196.78 (C¼¼O), 204.45
(C¼¼O). MS: m/z 552 (mþ2). Anal. Calcd. for C30H28O8S2: C,
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Acknowledgments. The authors are grateful to the Principal Ms.
Manju J. Nichani and Management of K.C. College, Mumbai for
providing necessary facilities and to the Head, Department of Mi-
crobiology for antimicrobial studies. Authors are also thankful to
the Director, Institute of Science, Mumbai (India) for providing
spectral analyses.
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