Convenient synthesis of some 4′-methtylthio-containing aryl and arylfuryl pyrazolines and their antimicrobial activity studies

Article abstract of DOI:10.1080/10426500500328939

The condensation of 4-acetylthioanisole with different aryl and aryfuryl aldehydes under aldol conditions affords α, β-unsaturated ketones (propenones), which undergo a facile and clean cyclization with hydrazines to give pyrazolines (4-6) in quantitative yields. The structures of newly synthesized compounds have been confirmed on the basis of spectral studies. All newly synthesized compounds were tested for their antibacterial and antifungal activity. Copyright Taylor & Francis Group, LLC.

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Convenient Synthesis of Some
4′-Methtylthio–Containing Aryl
and Arylfuryl Pyrazolines and
Their Antimicrobial Activity
Studies
Bantwal Shivarama Holla a , Manjathuru Mahalinga a
, Mithun Ashok a & Prakash Karegoudar a
a Department of Chemistry, Mangalore University,
Mangalagangothri, India
Published online: 01 Feb 2007.
To cite this article: Bantwal Shivarama Holla , Manjathuru Mahalinga , Mithun Ashok
& Prakash Karegoudar (2006) Convenient Synthesis of Some 4′-Methtylthio–Containing
Aryl and Arylfuryl Pyrazolines and Their Antimicrobial Activity Studies,
Phosphorus, Sulfur, and Silicon and the Related Elements, 181:6, 1427-1436, DOI:
10.1080/10426500500328939
To link to this article: http://dx.doi.org/10.1080/10426500500328939
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Phosphorus, Sulfur, and Silicon, 181:1427–1436, 2006
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500500328939
Convenient Synthesis of Some 4ꢀ-Methtylthio–Containing
Aryl and Arylfuryl Pyrazolines and Their Antimicrobial
Activity Studies
Bantwal Shivarama Holla
Manjathuru Mahalinga
Mithun Ashok
Prakash Karegoudar
Department of Chemistry, Mangalore University,
Mangalagangothri, India
The condensation of 4-acetylthioanisole with different aryl and aryfuryl aldehy-
des under aldol conditions affords α, β-unsaturated ketones (propenones), which
undergo a facile and clean cyclization with hydrazines to give pyrazolines (4–6)
in quantitative yields. The structures of newly synthesized compounds have been
confirmed on the basis of spectral studies. All newly synthesized compounds were
tested for their antibacterial and antifungal activity.
Keywords 4-Acetylthioanisole; aryfuryl aldehydes; antimcrobial; propenones;
pyrazolines
INTRODUCTION
Pyrazolines have been reported to show a broad spectrum of biologi-
cal activities, including antibacterial,1 antifungal,2 anti-inflammatory,3
antidepressant,4 and antiviral5 agents. Some these compounds have
also shown antidiabetic,6 anaesthetic,7 and analgesic properties.8 The
pyrazoline function is quite stable and has inspired chemists to utilize
this stable fragment in bioactive moieties to synthesize new compounds
Received June 6, 2005; accepted July 28, 2005.
The authors are grateful to the Head, R.S.I.C., Punjab University, Chandigarh, SAIF,
IISc Bangalore and Head, SAIF, I.I.T., Madras for providing elemental analysis, IR, 1H
NMR, and mass spectral data. The authors are also grateful to the Chairman, Department
of Biochemistry, Gulbarga University for providing antibacterial and antifungal activity
data for the compounds. The authors are greatful to Strides Research and Speciality
Chemicals Division, Mangalore for their cooperation and encouragement.
Address correspondence to Manjathuru Mahalinga, Mangalore University, De-
partment of Chemistry, Mangalagangothri 574199, India. E-mail: maliorganic100@
yahoo.co.in
1427

1428
B. S. Holla et al.
possessing biological activities, and the presence of SCH3 group in
molecules at strategic positions alters the activity. This prompted
us to synthesize various substituted pyrazoline derivatives. A clas-
sical synthesis of these compounds involves the base-catalyzed al-
dol condensation reaction of aromatic ketones and aldehydes to give
α, β-unsaturated ketones (propenones), which undergo a subsequent
cyclization reaction with hydrazines affording pyrazolines. In this
method, hydrazones are formed as intermediates, which can be sub-
sequently cyclized to 2-pyrazolines in the presence of suitable cyclizing
reagents.
RESULTS AND DISCUSSION
The newly prepared propenones were confirmed on the basis of IR, pro-
ton NMR, and mass spectral data. They show a characteristic IR ab-
sorption peak at ν = 1700–1660 cm−1, indicating the presence of a con-
jugated carbonyl group. As their NMR spectra suggests, the CH CH
are considerably shifted down field to the extent that they appear in the
aromatic region δ 6.5–8.5. As a result, these protons can hardly be dis-
1
tinguished from those of the aromatic rings. In the 400 MHz H NMR
spectrum of compounds 4–6, the pyrazolines, the CH2 protons of the
pyrazoline ring 6a, resonated as a pair of doublet of doublets in the
region δ 3.03–3.11 (J = 7.2 Hz, 7.5 Hz) and δ 3.75–3.85 (J = 12.2 Hz,
12.2 Hz), respectively, due to geminal and vicinal coupling. The CH
proton appeared as a doublet of doublets at δ 5.21–5.28 (J = 7.1 Hz,
7.1 Hz) due to vicinal coupling with the two magnetically nonequiv-
alent protons of the methylene group at position 4 of the pyrazoline
ring. The reaction probably involved the intermediate formation of hy-
drazones and subsequent addition of NH on the carbon-carbon double
bond of the propenone moiety.
As a result of our studies related to the development of the het-
erocyclic compounds, we report a synthesis of some new heterocyclic
compounds, which are found to be biologically active towards test or-
ganisms. We report in this article some aldol condensation reactions
between p-acetylthioanisole (2) with different aryl and arylfuryl alde-
hydes (1) in the presence of sodium hydroxide/methanol to give interme-
diate chalcones (3), which undergo a rapid cyclization with hydrazines.
The starting material 4-acetylthioanisole was prepared by Methods
A and B, and all arylfurfuraldehydes were synthesized through a
Meerwin reaction.9
3a: IR (KBr, cm−1): 3030, 2914.2 (Ar-H), 1649 (C O), 1127 (C F). 1H-
NMR (DMSO-d6) δ: 2.50 (s, 3H, SCH3), 6.99–6.96 (d, 2H, J = 8.84 Hz, 4-
methylthiolphenyl), 7.11–7.06 (d, 2H, J = 8.6 Hz, 4-methylthiophenyl),

4ꢀ- Methtylthio-Containing Aryl and Arylfuryl Pyrazolines
1429
SCHEME 1 Synthesis of substituted pyrazolines (4), (5), and (6).
7.44–7.40 and 7.77–7.73 (2d, 2H, J = 16 Hz, CH CH ), 7.61–7.60
(t, 2H, J = 5.4Hz, 4-fluorophenyl), 8.04–8.01 (d, 2H, J = 8.8 Hz,
4-fluorophenyl). MS: (M+, %); (272, 100), 225(35), 178(90), 152(20),
102(20), 69(38), 55(25). 3c: IR (KBr, cm−1): 3029, 2915 (Ar-H), 1665
(C O), 820 (C Cl), 1025 (C F). 1H-NMR (DMSO-d6): 2.55 (s, 3H,
SCH3), 6.77–6.76 (d, 1H, J = 3.5 Hz, furanyl), 6.81–6.79 (d, 1H, J =
3.5 Hz, furanyl), 7.33–7.31 (d, 2H, J = 8.4 Hz, 4-methylthiophenyl),
7.42–7.39 (2H, J = 8.5 Hz, 4-methylthiophenyl), 7.63–7.46 (2d, 2H, J
= 15.3 Hz, CH CH), 7.71–7.69 (d, 2H, J = 8.5 Hz, p-chlorophenyl),

1430
B. S. Holla et al.
8.00–7.98 (d, 2H, J = 8.3 Hz, 4-chlorophenyl). MS: (M+, %); (354, 100),
307 (22), 243 (20), 215 (20), 151 (30), 139 (50), 111 (12), 79(20), 57(10).
3d: IR (KBr, cm−1): 3032, 2930 (Ar-H), 1680 (C O), 815, 820, 822 (C Cl).
1H-NMR (DMSO-d6) δ: 2.55 (s, 3H, SCH3), 6.84–6.62 (d, 1H, J = 3.6 Hz,
furanyl), 7.27–7.26 (d, 2H, J = 3.6 Hz, furanyl), 7.27 (s, 1H, 2,4,5-
trichlorophenyl), 7.34–7.32 (d, 2H, J = 8.4Hz, 4-methylthiophenyl),
7.63–7.48 (2d, 2H, J = 15.3 Hz, CH CH), 8.00–7.93 (d, 2H, J = 8.5 Hz,
4-methylthiophenyl), 8.03 (s, 1H, 2,4,5-trichlorophenyl).
4a: IR (KBr, cm−1): 3036, 2928 (Ar-H), 1016 (C F). 1H-NMR (DMSO-
d6) δ: 2.39 (s, 3H, COCH3), 2.51 (s, 3H, SCH3), 3.13–3.06 (dd, 1H,
J = 4.5Hz, CH2), 3.76–3.66 (dd, 1H, J = 11.7 Hz, CH2), 5.58–5.52
(dd, 1H , J = 4.6 Hz, CH), 7.65–6.96 (m, 8H, Ar-H). MS: (M+, %);
(328, 65), 286(100), 269(8), 245(10), 225(22), 210(18), 191(10), 165(23),
149(30), 109(35), 77(36), 55(16). 4c: IR (KBr, cm−1): 3030, 2925 (Ar-H),
1
816 (C Cl). H-NMR (DMSO-d6) δ:1H-NMR (DMSO-d6) δ: 2.35 (s, 3H,
COCH3), 2.51 (s, 3H, SCH3), 3.47–3.35 (dd, 1H, J = 6.4 Hz, CH2), 3.75–
3.67 (dd, 1H, J = 12.1 Hz, CH2), 5.41-5.34 (dd, 1H, J = 6.9 Hz, CH),
7.67–6.20 (m, 8H, Ar-H). 5a: IR (KBr, cm−1): 3030, 2925 (Ar-H), 1734
1
(C O). H-NMR (DMSO-d6) δ: 2.32 (s, 3H, CH3), 2.51 (s, 3H, SCH3),
3.29–3.22 (dd, 1H, J = 4.9 Hz, CH2), 3.79–3.70 (dd, 1H, J = 11.7 Hz,
CH2), 5.81–5.75 (dd, 1H, J = 4.7 Hz, CH), 6.76–6.74 (d, 1H, J = 5.0 Hz,
thiophene ring), 7.08–7.06 (d, 1H, J = 5.0 Hz, thiophene ring), 7.28–7.25
(d, 2H, J = 6.7 Hz, 4-methylthiophenyl), 7.66–7.63 (d, 2H, J = 6.8 Hz,
4-methylthiophenyl), 8.88 (s, 1H, CHO). 6a: IR (KBr, cm−1): 3035, 2940
(Ar-H), 1026 (C F).1H-NMR (DMSO-d6) δ: 2.50 (s, 3H, SCH3), 3.11–
3.03 (dd, 1H, J = 7.2 Hz, CH2), 3.85–3.75 (dd, 1H, J = 12.2 Hz, CH2),
5.28–5.21 (dd, 1H, J = 7.1 Hz, CH), 7.64–6.76 (m, 13H, Ar-H). MS: (M+,
%); (362, 20), 149 (10), 122 (10), 109 (20), 91 (100), 77 (65), 58 (45). 6c:
IR (KBr, cm−1): 3030, 2928 (Ar-H), 816 (C Cl).1H-NMR (DMSO-d6) δ:
2.51 (s, 3H, SCH3), 3.45–3.37 (dd, 1H, J = 6.5 Hz, CH2), 3.78–3.68 (dd,
1H, J = 12.0 Hz, CH2), 5.41-5.34 (dd, 1H, J = 6.8 Hz, CH), 7.68–6.21
(m, 13H, Ar-H). MS: (M+, %); (444, 10), 354 (10), 305 (8), 266 (20), 178
(25), 151 (15), 149 (25), 115 (43), 77 (70), 57 (100). 6d: IR (KBr, cm−1):
3030, 2925 (Ar-H), 816, 820, 822 (C Cl). 1H-NMR (DMSO-d6) δ: 2.53 (s,
3H, SCH3), 3.43–3.37 (dd, 1H, J = 6.8 Hz, CH2), 3.79–3.71 (dd, 1H, J =
12.0 Hz, CH2), 5.43–5.38 (dd, 1H, J = 6.4 Hz, CH), 7.53–6.85 (m, 11H,
Ar-H).
BIOLOGICAL ACTIVITY
Antibacterial Studies
The newly synthesized compounds were screened for their antibac-
terial activity against Escherichia coli (ATTC-25922), Staphylococcus

4ꢀ- Methtylthio-Containing Aryl and Arylfuryl Pyrazolines
1431
TABLE I Antibacterial Activity of Compounds 4–6
Antibacterial activity (Zone of Inhibition in mm)
Compound no.
E. coli
S. aureus P. aeruginosa
K. pneumoniae
4a
4b
4c
4d
4e
4f
4g
5a
5b
5c
5d
5e
5f
6a
6b
6c
6d
6e
14
10
19
22
20
20
18
12
17
18
20
12
14
17
13
19
22
22
24
22
20
9
15
18
26
18
19
19
8
12
19
22
13
12
12
16
20
17
18
18
23
23
19
12
19
22
23
17
17
11
19
12
12
12
14
21
18
21
19
25
15
22
24
13
16
19
23
20
22
14
15
14
11
19
11
8
9
11
15
18
26
19
26
24
6f
6g
Ampicillin
aureus (ATTC-25923), Psuedomonus aeruginosa (ATTC-27853), and
Klebsiella pneumoniae (recultured) bacterial stains by the disc diffusion
method.10,11 The discs measuring 6.25 mm in diameter were punched
from Whatman no. 1 filter paper. Batches of 100 discs were dispensed
to each screw-capped bottle and sterilized by dry heat at 140◦C for
1 h. Test compounds were prepared with different concentrations using
dimethylformamide. Exactly 1 mL containing 100 times the amount of
chemical in each disc was added to each bottle, which contains 100 discs.
The discs of each concentration were placed in triplicate in a nutrient
agar medium separately seeded with fresh bacteria. The incubation
was carried out at 37◦C for 24 h. Ampicillin was used as a standard
drug. Solvent and growth controls were kept, and zones of inhibition
were noted. The results of such studies are given in the Table I. Among
the tested compounds, 4d, 6e, and 6g emerged as most active against
the tested organisms at a 10 µg concentration. It was interesting to
note that there was a drastic increase in the bacteriostatic activity in
the pyrazolines of arylfuraldehydes compared to the pyrazolines of aryl
aldehydes.

1432
B. S. Holla et al.
Antifungal Studies
Newly prepared compounds were screened for their antifungal activ-
ity against Aspergilus flavus (NICM No. 524), Aspergilus fumigatus
(NCIM No. 902), Candida albicans (NCIM No.300), and Penicillium
marneffei (recultured) in DMSO by the serial plate dilution method.14,15
Sabourands agar media was prepared by dissolving peptone (1 g), D-
glucose (4 g), and agar (2 g) in distilled water (100 mL) and adjusting
the pH to 5.7. Normal saline was used to make a suspension of a spore
of a fungal strain for inoculating. A loopful of particular fungal strain
was transferred to 3 mL of saline to get a suspension of the correspond-
ing species. Then 20 mL of agar media was poured into each petri dish.
Excess suspension was decanted, and plates were dried by placement in
an incubator at 37◦C for 1 h. Using an agar punch, wells were made into
each and were well labeled. A control was also prepared in triplicate and
maintained at 37◦C for 3–4 days. Antifungal activity was determined
by measuring the diameter of the inhibition zone (Table II). The activity
of each compound was compared with Flucanazole as the standard. Re-
sults of the antifungal activity study reveals that the compound 4d was
TABLE II Antifungal Activity of Compounds 4–6
Antifungal activity (Zone of Inhibition in mm)
Compound no.
A. flavus
A. fumigatus C. albicans P. marneffei
4a
4b
4c
4d
4e
4f
4g
5a
5b
5c
5d
5e
5f
6a
6b
6c
20
18
12
22
23
20
22
16
23
12
18
14
22
13
9
18
22
23
18
26
21
15
13
20
16
22
18
19
17
12
17
20
12
18
20
18
22
12
17
23
22
17
16
13
18
19
13
19
12
13
18
15
19
18
20
13
21
17
21
21
18
16
18
21
17
16
12
18
22
18
18
12
9
17
22
18
18
20
21
6d
6e
6f
6g
12
13
15
20
22
Flucanazole

4ꢀ- Methtylthio-Containing Aryl and Arylfuryl Pyrazolines
1433
active against Aspergilus flavus and Candida albicans. Compound 4e
was active against Aspergilus flavus, Aspergilus fumigatus, and Can-
dida albicans. Compound 6d was active against Aspergilus flavus and
Aspergilus fumigatus.
Conclusions
It appears that antimicrobial activity is enhanced by the presence of a
SCH3 group as a substituent on the benzene ring. Furthermore, it can
be concluded that compounds containing Cl and F groups in combina-
tion with a –SCH3 group as substituent on benzene rings can act as very
effective antimicrobial agents. Antibacterial and antifungal screening
results also indicate that pyrazolines of arylfuraldehydes are more ac-
tive than pyrazolines of aryl aldehydes.
EXPERIMENTAL
Melting points were determined by an open capillary method and
are uncorrected. The IR spectra (in KBr pellets) were recorded on a
Shimadzu FT-IR 157 spectrophotometer. PMR spectra were recorded
either on a Perkin-Elmer EM-390 (90 MHz) or on a Bruker WH-200
(270 MHz) spectrometer using TMS as an internal standard. Mass spec-
tra were recorded on a Jeol JMS-D 300 spectrometer operating at 70 Ev.
The purity of the compounds was checked by TLC on silica gel plates.
4-Acetyl Thioanisole
Method A
To a solution of thioanisole (100 g, 0.80 mol) in anhydrous chloroben-
zene (500 mL) anhydrous aluminium chloride (107.5 g, 0.80 mol) was
added under a nitrogen atmosphere. After cooling to −10◦C using an
ice-salt mixture, acetic anhydride (82.3 g, 0.80 mol) was added between
−10–5◦C. After completion of the addition, the temperature was raised
to 20–25◦C over a period of 30 min. The mixture was then quenched
with 2 L of ice cold water. The lower organic layer was separated and
washed with water to neutral. The organic solution was dried (Na2SO4).
The chlorobenzene was completely removed under reduced pressure.
The crude product was recrystallized from n-hexane white to a crys-
talline solid, yield 78 g, (58.3%), m.p. 81◦C (lit. 80–82◦C, Beil., 8(3),
296).

1434
B. S. Holla et al.
TABLE III Characterization Data of Propenones 3a–g
Molecular
formula
Yield
(%)
Compound no.
R
M.P.(◦C)
3a
3b
3c
3d
3e
3f
4-fluorophenyl
3-methylthienyl
4-chlorophenylfuryl
2,4,5-trichlorophenylfuryl
3,4-dichlorophenylfuryl
4-nitrophenylfuryl
C16H13FOS
C15H14OS2
C20H15ClO2S
C20H13Cl3O2S
80
82
83
81
80
85
82
112–113
132–133
195–197
188–189
185–186
194–196
165–167
C
20H14Cl3O2S
C20H15NO4S
C21H17NO4S
3g
3-methyl-4-nitrophenylfuryl
Method B
Phosphoryl chloride (123.4 g, 0.80 mol) was added dropwise to
the mixture containing N,N-dimethylacetamide (76.5 g, 0.96 mol) and
thioanisole (100 g, 0.80 mol) in dry chlorobenzene (300 mL) at 0–10◦C
with stirring. The mixture was kept at 80◦C for 2 hr, and then it was
poured into crushed ice and neutralized with sodium acetate. The or-
ganic phase was washed with sodium chloride solution, followed by
water. After concentrating under reduced pressure, the residue was ex-
tracted in n-hexane to obtain a white crystalline solid, yield 75 g, (56%),
m.p. 81◦C.
General Procedure for the Preparation of Propenones 3a–g
The method was reported in the literature.16 Characterization data are
given in Table III.
General Procedure for the Preparation of Pyrazolines 4a–g
A mixture of 3 (0.01 mol) and a molar equivalent of hydrazine hydrate
(80%) in glacial acetic acid (15 mL) was heated on a water bath at
90–95◦C for 5–6 h. The reaction mass then was poured into ice cold
water. The solid obtained was filtered, washed with water, dried, and
crystallized from ethanol to give 4a–g. Characterization data are given
in Table IV.
General Procedure for the Preparation of Pyrazolines 5a–f
A mixture of 3 (0.01 mol) and a molar equivalent of hydrazine hydrate
(80%) in formic acid (15 mL) was heated on a water bath at 100◦C for
3–5 h. The reaction mass was then poured into ice cold water and neu-
tralized with diluted sodium bicarbonate solution. The solid obtained
was filtered, washed with water, dried, and crystallized from ethanol to
give 5a–f. Characterization data are given in Table IV.

4ꢀ- Methtylthio-Containing Aryl and Arylfuryl Pyrazolines
1435
TABLE IV Characterization Data of Compounds 4–6
% Analysis
found (calculated)
Compound
no.
Molecular
formula
Yield M.P.
(%)
(◦C)
R
C
H
N
4a
4b
4c
4d
4e
4f
4-fluorophenyl
C18H17FN2OS
C17H18N2OS2
C22H19ClN2O2S
60 140–141 65.80 5.20
(65.83) (5.21) (8.53)
65 118–120 61.70 5.48
(61.78) (5.48) (8.47)
63 177–179 64.24 4.65
8.52
3-methylthienyl
8.40
4-chlorophenylfuryl
6.77
(64.30) (4.66) (6.81)
2,4,5-trichlorophenylfuryl C22H17Cl3N2O2S 65 170–171 55.10 3.51
5.82
(55.07) (3.57) (5.83)
3,4-dichlorophenylfuryl
4-nitrophenylfuryl
C22H18Cl2N2O2S 75 167–169 59.29 4.00
6.29
(59.33) (4.07) (6.29)
67 175–177 63.00 4.55
(62.69) (4.54) (9.96)
69 169–171 63.40 4.85
(63.43) (4.86) (9.64)
58 153–154 60.71 5.01
(60.72) (5.09) (8.85)
66 170–172 63.11 4.26
C22H19N3O4S
C23H21N3O4S
C16H16N2OS2
C21H17ClN2O2S
9.99
4g
5a
5b
5c
5d
5e
5f
3-methyl-4-
nitrophenylfuryl
3-methylthienyl
9.62
8.86
4-chlorophenylfuryl
7.05
(63.55) (4.31) (7.05)
2,4,5-trichlorophenylfuryl C21H15Cl3N2O2S 70 182–184 54.13 3.22
6.02
(54.15) (3.24) (6.01)
3,4-dichlorophenylfuryl
4-nitrophenylfuryl
C21H16Cl2N2O2S 77 174–176 58.44 3.73
6.48
(58.47) (3.73) (6.49)
78 180–182 61.88 4.12 10.31
(61.90) (4.20) (10.31)
65 176–178 62.66 4.55
(62.69) (4.54) (9.96)
56 140–142 72.88 5.23
(72.90) (5.28) (7.72)
70 148–150 69.20 5.50
(69.19) (5.52) (7.68)
64 176–177 70.00 4.75
(70.17) (4.75) (6.29)
65 182–184 60.77 3.71
(60.77) (3.72) (5.45)
56 170–172 65.13 4.21
C21H17N3O4S
C22H19N3O4S
C22H19FN2S
C21H20N2S2
3-methyl-4-
nitrophenylfuryl
4-fluorophenyl
9.96
6a
6b
6c
6d
6e
6f
7.74
3-methylthienyl
7.67
4-chlorophenylfuryl
C26H21ClN2OS
6.26
2,4,5-trichlorophenylfuryl C26H19Cl3N2OS
5.44
3,4-dichlorophenylfuryl
4-nitrophenylfuryl
C26H20Cl2N2OS
C26H21N3O3S
C27H23N3O3S
5.81
(65.13) (4.20) (5.84)
58 190–192 68.55 4.63
(68.55) (4.64) (5.22)
60 188–190 69.00 4.93
5.21
6g
3-methyl-4-
8.91
nitrophenylfuryl
(69.06) (4.93) (8.94)
General Procedure for the Preparation of Pyrazolines 6a–g
A mixture of 3 (0.01 mol) and a molar equivalent of phenylhydrazine in
glacial acetic acid (15 mL) was heated on a water bath at 90–95◦C for
5–6 h. The reaction mass was then poured into ice cold water. The solid

1436
B. S. Holla et al.
obtained was filtered, washed with water, dried, and crystallized from
ethanol to give 5a–g. Characterization data are given in Table IV.
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