Synthesis of 3-(4-fluorophenyl)-3-(furan-2-yl)propanoic acid and 5-[2-(4-fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-oxadiazole-2-thiol derivatives

Article abstract of DOI:10.1134/S1070363215050084

Synthesis of 3-(4-fluorophenyl)-3-furan-2-ylpropionyl chloride has been performed, and selected transformations of the product have been studied.

Full text of DOI:10.1134/S1070363215050084

ISSN 1070-3632, Russian Journal of General Chemistry, 2015, Vol. 85, No. 5, pp. 1052–1056. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © N.S. Arutyunyan, L.A. Akopyan, T.A. Markaryan, R.V. Paronikyan, G.A. Panosyan, G.A. Gevorgyan, 2015, published in Zhurnal
Obshchei Khimii, 2015, Vol. 85, No. 5, pp. 755–759.
Synthesis of 3-(4-Fluorophenyl)-3-(furan-2-yl)propanoic Acid and
5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-oxadiazole-2-thiol
Derivatives
N. S. Arutyunyana, L. A. Akopyana, T. A. Markaryana,
R. V. Paronikyana, G. A. Panosyanb, and G. A. Gevorgyana
a Scientific Technological Center of Organic and Pharmaceutical Chemistry,
National Academy of Sciences of the Republic of Armenia, Mnjoyan Institute of Fine Organic Chemistry,
ave. Azatutyan 26, Yerevan, 0014 Armenia
e-mail: gyulgev@gmail.com
b Scientific Technological Center of Organic and Pharmaceutical Chemistry,
National Academy of Sciences of the Republic of Armenia, Molecule Structure Research Center, Yerevan, Armenia
Received January 15, 2015
Abstract—Synthesis of 3-(4-fluorophenyl)-3-furan-2-ylpropionyl chloride has been performed, and selected
transformations of the product have been studied.
Keywords: acylation, hydrolysis, propionamide, acetamide, alcoholysis
DOI: 10.1134/S1070363215050084
3-(4-Fluorophenyl)-3-furan-2-ylpropionic acid II
was obtained via hydrolysis of 3-(4-fluorophenyl)-3-
(furan-2-yl)propane nitrile I synthesized earlier [1].
Reaction of the acid with thionyl chloride resulted in
chloride IIa. Acylation of various amines with chloride
IIa afforded the corresponding propanamides III–
XIII. Reaction of the acid chloride with anhydrous
ethanol yielded ethyl ester IIb. The latter reacted with
hydrazine hydrate to give 3-(4-fluorophenyl)-3-(furan-
2-yl)propionic acid hydrazide XIV. Interaction of XIV
with carbon disulfide in alkaline medium led to 5-[2-
(4-fluorophenyl)-2-(furan-2-yl)-ethyl]-1,3,4-oxadiazole-
2-thiol XV; reactions of the latter with various
chloroacetamides and aryl(alkyl) halides afforded the
corresponding amides XVI–XVIII and oxadiazole
derivatives XIX–XXI (Scheme 1).
3-(4-Fluorophenyl)-3-(furan-2-yl)propanoic acid
(II). A mixture of 22.4 g (0.4 mol) of KOH, 80 mL of
ethylene glycol, and 21 g (0.1 mol) of nitrile I was
refluxed during 6 h. After cooling, the mixture was
diluted with 80 mL of water and extracted with diethyl
ether. The aqueous layer was acidified with 40 mL of
conc. HCl and acid II was extracted with benzene
(3 × 100 mL). The benzene layer was washed with
water and dried. After removal of benzene the residue
was distilled in vacuum. Yield 19 g (83%) bp 175–
177°C (2 mmHg). IR spectrum, ν, cm–1: 3400–3200
1
(OH), 1710 (C=O), 1610–1590 (C=CAr). H NMR
spectrum, δ, ppm: 2.76 d.d (1H, CH2, J 15.9, 8.1 Hz),
2.95 d.d (1H, CH2, J 15.9, 7.3 Hz), 4.46 d.d (1H, CH,
J 8.1, 7.3 Hz), 6.07 d.d (1H, H3furan, J 3.2, 0.8 Hz), 6.26
d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.95–7.03 m (2H,
C6H4F), 7.20–7.27 m (2H, C6H4F), 7.33 d.d (1H, H5
,
furan
Structures of the prepared compounds were
confirmed by IR and NMR spectroscopy.
J 1.9, 0.8 Hz), 11.95 br.s (1H, OH). Found, %: C 67.0;
H 5.04. C13H11O3. Calculated, %: C 66.66; H 4.73.
EXPERIMENTAL
3-(4-Fluorophenyl)-3-(furan-2-yl)propanoyl chloride
(IIa). A mixture of 23 g (0.11 mol) of acid II, 13.1 g
(0.11 mol) of SOCl2, and 50 mL of benzene was
refluxed during 2 h. After benzene removal, the resulting
acid chloride was used without further purification.
IR spectra were recorded using a Nicolet AVATAR
330 FT-IR spectrophotometer. H NMR spectra were
registered with a Mercury VX-300 spectrometer
(300 MHz) in DMSO-d6–CCl4 relative to internal TMS
as reference.
1
1052

SYNTHESIS OF 3-(4-FLUOROPHENYL)-3-(FURAN-2-YL)PROPANOIC ACID
1053
Scheme 1.
O
O
NR1R2
R1R2NH
O
O
O
O
O
N
OH−
F
OH
Cl
III_ХIII
SOCl2
O
O
F
I
F
II
F
IIa
O
EtOH
F
IIb
N N
N N
NH_NH2
NHR3
O
O
O
O
SH
S
O
O
O
NHR3
Cl
NH2_NH2
CS2, KOH
O
F
ХV
F
ХIV
F
ХVI_ХVIII
Cl
C2H5Br
Br
O
C6H6CH2Cl
N N
N N
O
N N
O
O
O
O
O
S
S
S
O
Cl
F
F
F
ХIХ
ХХ
ХХI
R1 = H, R2 = 1-phenylethyl (III), (CH2)3N(CH3)2 (IV), thiazol-2-yl (V), 3-MeC6H4 (VI), 4-MeOC6H4 (VII), Bn (VIII),
4-ClC6H4 (IX), cyclohexyl (X), 2-MeOC6H4 (XI), α-naphthyl (XII); NR1R2 = N,N-diethyl (XIII), R3 = H (XVI), 4-ClC6H4
(XVII), furan-2-ylmethyl (XVIII).
3-(4-Fluorophenyl)-3-(furan-2-yl)propanamides
(III–XIII) (general procedure). Equimolar amount of
the acid chloride IIa was added dropwise to a solution
of 0.01 mol of the amine and 0.01 mol of triethylamine
in anhydrous benzene upon stirring. The mixture was
refluxed during 3 h, cooled, and acidified with a
solution of HCl until slightly acidic reaction. The
reaction products were extracted with benzene; the
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1054
ARUTYUNYAN et al.
extract was washed with water, dried, and evaporated.
The residue was distilled (III, IV, VI, and XIII) or
recrystallized from ethanol (V and VII–XII).
m (2H, C6H4F), 7.05 t (1H, C6H4CH3), 7.22–7.29 and
7.33–7.36 m (5H, Harom), 9.55 br.s (1H, NH). Found,
%: C 74.92; H 6.11; N 5.82. C20H18FNO2. Calculated,
%: C 74.29; H 5.61; N 4.33.
N-(1-Phenylethyl)-3-(4-fluorophenyl)-3-(furan-2-
yl)propanamide (III). Yield 61%, bp 225–230°C
(4 mmHg). IR spectrum, ν, cm–1: 3270 (NH), 1642 (C=O).
1H NMR spectrum, δ, ppm: 1.24 d and 1.33 d (3H,
CH3, J 7.0 Hz), 2.63–2.87 m (2H, CH2), 4.46–4.53 m
(1H, CHCH2), 4.80–4.91 m (1H, CHCH3), 6.07 d.d
and 6.09 d.d (1H, H3furan, J 3.2, 0.8 Hz), 6.25 d.d and
6.27 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.89–7.01 and
7.10–7.26 m (9H, C6H4, C6H5), 7.31 d.d and 7.34 d.d
(1H, H5furan, J 1.9, 0.8 Hz), 8.00 br.d (1H, NH, J
7.9 Hz). Found, %: C 75.02; H 6.45; N 4.67.
C21H20FNO2. Calculated, %: C 74.76; H 5.97; N 4.15.
N-(4-Methoxyphenyl)-3-(4-fluorophenyl)-3-(furan-
2-yl)propanamide (VII). Yield 62%, mp 148–150°C.
1
IR spectrum, ν, cm–1: 3304 (NH), 1656 (C=O). H
NMR spectrum, δ, ppm: 2.82 d.d and 2.99 d.d (2H,
O=CCH2, J 14.6, 7.4 Hz), 3.73 s (3H, OCH3), 4.60 d.d
(1H, ArCH, J 8.0, 7.4 Hz), 6.14 d.d (1H, H3furan, J 3.2,
0.9 Hz), 6.28 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.71–6.76
m (2H, C6H4OMe), 6.95–7.03 m (2H, C6H4F), 7.22–
7.29 m (2H, C6H4F), 7.35–7.40 m (2H, C6H4OMe),
7.36 d.d (1H, H5furan, J 1.9, 0.9 Hz), 9.55 br.s (1H,
NH). Found, %: C 71.25; H 5.90; N 4.68. C20H18FNO3.
Calculated, %: C 70.79; H 5.35; N 4.13.
N-[3-(Dimethylamino)propyl]-3-(4-fluorophenyl)-
3-(furan-2-yl)propanamide (IV). Yield 64%, bp 210–
214°C (4 mmHg). IR spectrum, ν, cm–1: 3280 (NH),
N-Benzyl-3-(4-fluorophenyl)-3-(furan-2-yl)pro-
panamide (VIII). Yield 65%, mp 118–120°C. IR spec-
trum, ν, cm–1: 3261 (NH), 1640 (C=O). 1H NMR spec-
trum, δ, ppm: 2.72 d.d and 2.86 d.d (2H, CHCH2, J
14.2, 7.0 Hz), 4.14 d.d and 4.28 d.d (2H, NCH2, J 15.1,
6.2 Hz), 4.55 d.d (1H, CHAr, J 8.7, 7.0 Hz), 6.09 d.d
(1H, H3furan, J 3.2, 0.9 Hz), 6.26 d.d (1H, H4furan, J 3.2,
1.8 Hz), 6.92–7.00 m and 7.13–7.27 m (9H, C6H5,
C6H4F), 7.33 d.d (1H, H5furan, J 1.8, 0.9 Hz), 8.09 br.d.d
(1H, NH, J 6.2, 5.5 Hz). Found, %: C 74.83; H 6.00; N
4.82. C20H18FNO2. Calculated, %: C 74.29; H 5.61; N 4.33.
1
1654 (C=O). H NMR spectrum, δ, ppm: 1.37–1.46 m
(2H, NCH2), 2.08 t (2H, NH2, J 7.1 Hz), 2.10 s (6H,
CH3NCH3), 2.60 d.d (1H, CH2CH, J 14.2, 8.3 Hz),
2.76 d.d (1H, CH2C=O, J 14.2, 7.2 Hz), 2.96–3.04 m
(2H, HNCH2), 4.50 d.d (1H, CHC6H4, J 8.3, 7.2 Hz),
6.08 d.d (1H, H3furan, J 3.2, 0.8 Hz), 6.25 d.d (1H,
H4furan, J 3.2, 1.8 Hz), 6.91–6.99 m and 7.17–7.24 m
(4H, C6H4F), 7.32 d.d (1H, H5furan, J 1.8, 0.8 Hz), 7.57
br. t (1H, NH, J 5.6 Hz). Found, %: C 68.20; H 7.64; N
9.32. C18H29FN2O2. Calculated, %: C 67.90; H 7.28; N
8.80.
3-(4-Fluorophenyl)-3-(furan-2-yl)-N-(4-chloro-
phenyl)propanamide (IX). Yield 61%, mp 138–140°C.
IR spectrum, ν, cm–1: 3296 (NH), 1660 (C=O). 1H NMR
spectrum, δ, ppm: 2.86 d.d and 3.03 d.d (2H, CH2, J
14.9, 7.4 Hz), 4.61 d.d (1H, CH, J 8.2, 7.4 Hz), 6.12
d.d (1H, H3furan, J 3.2, 0.9 Hz), 6.27 d.d (1H, H4furan, J
3.2, 2.0 Hz), 6.94–7.02 m (2H, C6H4F), 7.14–7.19 m
(2H, C6H4Cl), 7.22–7.29 (2H, C6H4F), 7.34 d.d (1H,
H5furan, J 2.0, 0.9 Hz), 7.50–7.55 m (2H, C6H4Cl), 9.79
br.s (1H, NH). Found, %: C 66.83; H 4.85; N 4.67.
C19H15ClFNO2. Calculated, %: C 66.38; H 4.40; N
4.07.
N-(Thiazol-2-yl)-3-(4-fluorophenyl)-3-(furan-2-
yl)propanamide (V). Yield 58%, mp 162–164°C. IR
1
spectrum, ν, cm–1: 3270 (NH), 1685 (C=O). H NMR
spectrum, δ, ppm: 3.01 d.d and 3.15 d.d (2H, O=CCH2,
J 15.1, 7.5 Hz), 4.67 d.d (1H, ArCH, J 7.9, 7.5 Hz),
6.13 d.d (1H, H3furan, J 3.2, 7.09 Hz), 6.27 d.d (1H,
H4furan, J 3.2, 1.8 Hz), 6.93 d (1H, CHS, J 3.5 Hz),
6.95–7.03 m and 7.23–7.30 (4H, C6H4), 7.33 d (1H,
=CHN, J 3.5 Hz), 7.35 d.d (1H, H5furan, J 1.8, 0.9 Hz),
12.04 br.s (1H, NH). Found, %: C 61.15; H 4.57; N
9.30. C16H13FN2O2S. Calculated, %: C 60.75; H 4.14;
N 8.86.
3-(4-Fluorophenyl)-3-(furan-2-yl)-N-cyclohexyl-
propanamide (X). Yield 59%, mp 98°C. IR spectrum,
1
N-(3-Methylphenyl)-3-(4-fluorophenyl)-3-(furan-
2-yl)propanamide (VI). Yield 64%, bp 225–228°C
(2 mmHg). IR spectrum, ν, cm–1: 3292 (NH), 1652
ν, cm–1: 3284 (NH), 1636 (C=O). H NMR spectrum,
δ, ppm: 0.90–1.36 m and 1.52–1.73 (10H, C6H11), 2.57
d.d and 2.74 d.d (2H, CH2, J 14.1, 7.2 Hz), 3.39–3.52
m (1H, NCH), 4.49 d.d (1H, ArCH, J 8.4, 7.2 Hz),
6.08 d.d (1H, H3furan, J 3.2, 0.9 Hz), 6.25 d.d (1H,
H4furan, J 3.2, 1.8 Hz), 6.91–6.99 m (2H, C6H4F), 7.15–
7.23 m (2H, C6H4F), 7.29 br.d (1H, NH, J 7.7 Hz),
7.31 d.d (1H, H5furan, J 1.8, 0.9 Hz). Found, %: C
1
(C=O). H NMR spectrum, δ, ppm: 2.30 s (3H, CH3),
2.85 d.d and 3.02 d.d (1H, O=CCH2, J 14.8, 7.3 Hz),
4.62 d.d (1H, ArCH, J 8.1, 7.3 Hz), 6.14 d.d (1H,
H3furan, J 3.2, 0.9 Hz), 6.27 d.d (1H, H4furan, J 3.2,
1.8 Hz), 6.75 br.d (1H, C6H4CH3, J 7.6 Hz), 6.94–7.02
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SYNTHESIS OF 3-(4-FLUOROPHENYL)-3-(FURAN-2-YL)PROPANOIC ACID
1055
71.05; H 7.25; N 5.32. C17H20FNO2. Calculated, %: C
70.57; H 6.97; N 4.84.
J 1.9 Hz), 8.91 br.s (1H, NH). Found, %: C 63.15; H
5.80; N 11.67. C13H13FN2O2. Calculated, %: C 62.90;
H 5.28; N 11.28.
N-(4-Methoxyphenyl)-3-(4-fluorophenyl)-3-(furan-
2-yl)propanamide (XI). Yield 60%, mp 223–225°C
(2 mmHg). IR spectrum, ν, cm–1: 3304 (NH), 1660
5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-
oxadiazole-2-thiol (XV). 1.7 g (0.03 mol) of KOH
was added to a solution of 6.2 g (0.025 mol) of com-
pound XIV in 50 mL of ethanol. The mixture was
refluxed during 0.5 h; 6 mL of carbon disulfide was
added after cooling, and the mixture was further
refluxed during 30–35 h. Ethanol was distilled off; the
residue was dissolved in water and acidified with
hydrochloric acid (1 : 1). The precipitated crystals
were filtered off, washed with water, and recrystallized
from ethanol. Yield 6.5 g (78%), mp 95–96°C. IR
spectrum, ν, cm–1: 3150 (SH), 1628 (C=N), 1604, 1590
(Ar). 1H NMR spectrum, δ, ppm: 3.29 d.d and 3.46 d.d
(2H, CH2, J 15.5, 7.8 Hz), 4.56 d.d (1H, CHAr, J 8.1,
7.8 Hz), 6.16 d.d (1H, H3furan, J 3.2, 0.8 Hz), 6.29 d.d
(1H, H4furan, J 3.2, 1.9 Hz), 6.98–7.06 m and 7.26–7.33
m (4H, C6H4F), 7.38 d.d (1H, H5furan, J 1.9, 0.8), 13.80
br.s (1H, SH). Found, %: C 58.38; H 4.26; N 10.12.
C14H11FN2O2S. Calculated, %: C 57.92; H 3.82; N
9.65.
1
(C=O). H NMR spectrum, δ, ppm: 2.97 d.d and 3.14
d.d (1H, CH2, J 14.8, 7.2 Hz), 3.84 s (3H, OCH3), 4.60
d.d (1H, CH, J 8.1, 7.2 Hz), 6.15 d.d (1H, H3furan, J 3.2,
0.9 Hz), 6.27 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.79–6.88
m and 6.92–7.02 m (9H, C6H4F, OCH3), 7.24–7.31 m
(2H, C6H4F), 7.34 d.d (1H, H5furan, J 1.9, 0.9 Hz), 7.97
br.d (1H, C6H4OMe, J 7.9 Hz), 8.62 br.s (1H, NH).
Found, %: C 71.13; H 5.84; N 4.62. C20H18FNO3.
Calculated, %: C 70.79; H 5.35; N 4.13.
N-(Naphthalen-1-yl)-3-(4-fluorophenyl)-3-(furan-
2-yl)propanamide (XII). Yield 58%, mp 178–180°C.
IR spectrum, ν, cm–1: 3294 (NH), 1645 (C=O). 1H NMR
spectrum, δ, ppm: 3.06 d.d and 3.15 d.d (2H, CH2, J
14.1, 7.0 Hz), 4.63 d.d (1H, CHAr, J 8.6, 7.0 Hz), 6.17
br.d (1H, H3furan, J 3.1 Hz), 6.51 br.d (1H, H4furan, J
3.1 Hz), 6.99–7.08 (2H, C6H4F), 7.27–7.82 m (10 H,
Harom), 9.73 br.s (1H, NH). Found, %: C 77.85; H 6.74;
N 4.00. C23H18FNO2. Calculated, %: C 77.10; H 6.21;
N 3.60.
Compounds XVI–XXI (general procedure). A
mixture of 50 mL of ethanol, 0.07 mol of compound
XV, and 0.07 mol of KOH was heated during several
minutes and mixed with a solution of chloroacetamide
or alkyl(aryl-alkyl)halide in ethanol. The reaction
mixture was incubated overnight; the precipitate was
filtered off, washed several times with water, dried,
and recrystallized from ethanol.
N,N-Diethyl-3-(4-fluorophenyl)-3-(furan-2-yl)pro-
panamide (XIII). Yield 62%, bp 160°C (1 mmHg). IR
1
spectrum, ν, cm–1: 1665 (C=O). H NMR spectrum, δ,
ppm: 0.98 t (3H, CH3, J 7.1 Hz), 1.08 t (3H, CH3, J
7.1 Hz), 2.80 d.d and 2.96 d.d (1H, CH2C=O, J 15.3,
6.6 Hz), 3.19–3.28 m (4H, CH2NCH2), 4.61 d.d (1H,
CHAr, J 7.9, 6.6 Hz), 6.04 d.d (1H, H3furan, J 3.2,
0.8 Hz), 6.26 d.d (1H, H4furan, J 3.2, 1.8 Hz), 6.92–7.00
2-{5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-
oxadiazol-2-ylsulfanyl}acetamide (XVI). Yield 58%,
mp 90–92°C. IR spectrum, ν, cm–1: 3328, 3615 (NH2),
m and 7.20–7.26 m (4H, C6H4F), 7.33 d.d (1H, H5
,
furan
J 1.8, 0.8 Hz). Found, %: C 71.05; H 7.32; N 5.25.
C17H20FNO2. Calculated, %: C 70.57; H 6.97; N 4.84.
1
1675 (C=O). H NMR spectrum, δ, ppm: 3.41 d.d and
3.57 d.d (2H, CH2CH, J 15.4, 7.6 Hz), 3.90 s (2H,
SCH2), 4.58 d.d (1H, CHAr, J 8.2, 7.6 Hz), 6.15 d.d
(1H, H3furan, J 3.2, 0.8 Hz), 6.29 d.d (1H, H4furan, J 3.2,
1.9 Hz), 6.97–7.05 m and 7.24–7.31 m (4H, C6H4F),
3-(4-Fluorophenyl)-3-(furan-2-yl)propane hyd-
razide (XIV). A mixture of 0.015 mol of the chloride
IIa in 100 mL of anhydrous ethanol was refluxed
during 5–6 h. After removal of ethanol, the residue
(0.03 mol, ester IIb) and 0.045 mol of hydrazine
hydrate were refluxed in isobutyl alcohol during 6 h
and then cooled. The crystalline hydrazide was filtered
off and recrystallized from ethanol. Yield 73%, mp
125–127°C. IR spectrum, ν, cm–1: 3312, 3278 (NH2).
1H NMR spectrum, δ, ppm: 2.59 d.d and 2.75 d.d (2H,
CH2, J 14.5, 7.4 Hz), 3.86 br.s (2H, NH2), 4.52 d.d
(1H, CHAr, J 8.2, 7.4 Hz), 6.09 br.d (1H, H3furan, J
3.2 Hz), 6.25 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.92–7.00
7.07 br.s and 7.51 br.s (2H, NH2), 7.38 d.d (1H, H5
,
furan
J 1.9, 0.8 Hz). Found, %: C 55.90; H 4.68; N 12.70.
C16H14FN3O3S. Calculated, %: C 55.32; H 4.06; N
12.10.
2-{5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-
oxadiazol-2-ylsulfanyl}-N-(4-chlorophenyl)acetamide
(XVII). Yield 54%, mp 136–138°C. IR spectrum, ν,
1
cm–1: 3344 (NH), 1656 (C=O). H NMR spectrum, δ,
ppm: 3.41 d.d and 3.58 d.d (2H, CH2CH, J 15.5,
m and 7.17–7.24 m (4H, C6H4F), 7.32 br.d (1H, H5
,
7.6 Hz), 4.14 s (2H, SCH2), 6.14 d.d (1H, H3furan, J 3.2,
furan
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1056
ARUTYUNYAN et al.
0.8 Hz), 6.28 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.95–7.03
m and 7.23–7.30 m (4H, C6H4F), 7.21–7.25 m and
7.56–7.61 m (4H, C6H4Cl), 7.37 d.d (1H, H5furan, J 1.9,
0.8 Hz), 10.30 s (1H, NH). Found, %: C 58.42; H 4.15;
N 9.95. C22H17CIFN3O3S. Calculated, %: C 57.71; H
3.74; N 9.18.
Found, %: C 60.15; H 4.17; N 7.00. C22H16ClFN2O3S.
Calculated, %: C 59.66; H 3.64; N 6.32.
2-(Benzylsulfanyl)-5-[2-(4-fluorophenyl)-2-(furan-
2-yl)ethyl]-1,3,4-oxadiazole (XX). Yield 55%, mp 48°C.
1
IR spectrum, ν, cm–1: 1580, 1610 (Ar). H NMR spec-
trum, δ, ppm: 3.40 d.d and 3.57 d.d (2H, CH2CH, J
15.4, 7.6 Hz), 4.38 s (2H, SCH2), 4.55 d.d (1H, CHAr,
J 8.2, 7.6), 6.13 br.d (1H, H3furan, J 3.2 Hz), 6.28 d.d
(1H, H4furan, J 3.2, 1.9 Hz), 6.95–7.03 m and 7.22–7.38
m (4H, C6H4F), 7.30–7.38 m (6H, C6H5, H5furan). Found,
%: C 66.90; H 5.00; N 7.00 C21H17FN2O2S. Calcu-
lated, %: C 66.30; H 4.50; N 7.36.
2-{5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-
oxadiazol-2-ylsulfanyl}-N-(furan-2-ylmethyl)acetamide
(XVIII). Yield 60%, mp 93–95°C. IR spectrum, ν, cm–1:
1
3303 (NH), 1650 (C=O). H NMR spectrum, δ, ppm:
3.40 d.d and 3.57 d.d (2H, CH2CH, J 15.5, 7.6 Hz),
3.93 s (2H, SCH2), 4.31 d (2H, NCH2, J 5.6 Hz), 4.57
d.d (1H, CHAr, J 8.3, 7.6 Hz), 6.15 d. t and 6.21 d.d
(2H, H3furan, J 3.3, 0.9 Hz), 6.28 d.d and 6.30 d.d (1H,
H4furan, J 3.3, 1.9 Hz), 6.96–7.04 m and 7.24–7.31 m
(4H, C6H4F), 7.37 d.d and 7.38 d.d (2H, H5furan, J 1.9,
0.9 Hz), 8.56 br. t (1H, NH, J 5.6 Hz). Found, %: C
59.87; H 4.95; N 10.27. C21H18FN3O4S. Calculated, %:
C 59.01; H 4.25; N 9.83.
2-(Ethylsulfanyl)-5-[2-(4-fluorophenyl)-2-(furan-
2-yl)ethyl]-1,3,4-oxadiazole (XXI). Yield 55%, mp
36°C. IR spectrum, ν, cm–1: 1628 (C=N), 1610, 1584
1
(Ar). H NMR spectrum, δ, ppm: 1.40 t (3H, CH3, J
7.3 Hz), 3.15 q (2H, SCH2, J 7.3 Hz), 3.41 d.d and
3.58 d.d (2H, CH2CH, J 15.4, 7.6 Hz), 4.57 d.d (1H,
CHAr, J 8.3, 7.6 Hz), 6.14 d.d (1H, H3furan, J 3.2,
0.8 Hz), 6.28 d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.96–7.04
m and 7.24–7.31 m (4H, C6H4F). Found, %: C 61.00;
H 5.27; N 9.38. C16H15FN2O2S. Calculated, %: C
60.36; H 4.75; N 8.80.
2-{5-[2-(4-Fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-
oxadiazol-2-ylsulfanyl}-1-(4-chlorophenyl)ethanone
(XIX). Yield 57%, mp 95–96°C. IR spectrum, ν, cm–1:
1
1685 (C=O), 1600, 1587 (Ar). H NMR spectrum, δ,
ppm: 3.41 d.d and 3.58 d.d (2H, CH2CH, J 15.4,
7.6 Hz), 4.56 d.d (1H, CHAr, J 8.2, 7.6 Hz), 4.89 s
(2H, SCH2), 6.14 d.d (1H, H3furan, J 3.2, 0.8 Hz), 6.28
d.d (1H, H4furan, J 3.2, 1.9 Hz), 6.96–7.04 m and 7.23–
7.30 m (4H, C6H4F), 7.37 d.d (1H, H5furan, J 1.9,
0.8 Hz), 7.50–7.54 m and 8.01–8.06 m (4H, C6H4Cl).
REFERENCE
1. Arutyunyan, N.S., Akopyan, L.A., Snkhchyan, G.M.,
Papoyan, O.A., Panosyan, G.A., and Gevorgyan, G.A.,
Chem. Heterocycl. Compd., 2006, vol. 42, no. 4, p. 449.
DOI: 10.1007/s10593-006-0108-0.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 5 2015