Synthesis of 7-acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-dimethyl-3- thioxo-8-phenyl(heteryl)isoquinoline-4-carbonitriles Based on 2,4-Diacetyl-5-hydroxy-5-methyl-3-phenyl(heteryl)cyclohexanones

Article abstract of DOI:10.1134/S1070363210100257

7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-dimethyl-3-thioxo-8- phenyl(heteryl)isoquinoline-4-carbonitriles were obtained by reaction of 2,4-diacetyl-5-hydroxy-5-methyl-3-phenyl(heteryl)cyclohexanones with cyanothioacetamide. Structure of 7-acetyl-5,6,7,8-tetrahydro-6-hydroxy-1,6- dimethyl-3-methylthio-8-phenylisoquinoline-4-carbonitrile was proved by X-ray diffraction method.

Full text of DOI:10.1134/S1070363210100257

ISSN 1070-3632, Russian Journal of General Chemistry, 2010, Vol. 80, No. 10, pp. 2037–2042. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © V.D. Dyachenko, S.M. Sukach, A.D. Dyachenko, R.I. Zubatyuk, O. V. Shishkin, 2010, published in Zhurnal Obshchei Khimii, 2010,
Vol. 80, No. 10, pp. 1728–1733.
Synthesis of 7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-
1,6-dimethyl-3-thioxo-8-phenyl(heteryl)isoquinoline-
4-carbonitriles Based on 2,4-Diacetyl-5-hydroxy-5-methyl-
3-phenyl(heteryl)cyclohexanones
V. D. Dyachenkoa, S. M. Sukacha, A. D. Dyachenkoa,
R. I. Zubatyukb, and O. V. Shishkinb
a Taras Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011 Ukraine
fax: (0642)530008
е-mail: dvd_lug@online.lg.ua
b Scientific-Technological Concern “Institute of Single Crystals,”
National Academy of Sciences of Ukraine, Kharkov, Ukraine
Received November 24, 2009
Abstract—7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-dimethyl-3-thioxo-8-phenyl(heteryl)isoquinoline-4-
carbonitriles were obtained by reaction of 2,4-diacetyl-5-hydroxy-5-methyl-3-phenyl(heteryl)cyclohexanones
with cyanothioacetamide. Structure of 7-acetyl-5,6,7,8-tetrahydro-6-hydroxy-1,6-dimethyl-3-methylthio-8-
phenylisoquinoline-4-carbonitrile was proved by X-ray diffraction method.
DOI: 10.1134/S1070363210100257
Tetrahydroisoquinoline derivatives are semiproducts
in the synthesis of biologically active compounds,
which can be used in medicine as drugs [1, 2]. The iso-
quinoline frame is a basic structural component of the
large number of natural alkaloids, which possess
pharmacological action [3–5].
hexanones Iа–Id with cyanothioacetamide II in
anhydrous ethanol in the presence of morpholine was
examined. This condensation was shown to occur to
form evidently intermediates А, which underwent the
intramolecular cyclization into 7-acetyl-2,3,5,6,7,8-
hexahydro-6-hydroxy-1,6-dimethyl-3-thioxo-8-phenyl-
(heteryl)isoquinoline-4-carbonitriles IIIа–IIId.
Owing to the increasing practical value of iso-
quinilines, the attention is concentrated on the
development of the methods of their synthesis.
Building up of a heterocyclic system on a carbocycle is
the most common of them [6].
The structure of 7-acetyl-3-benzoylthio-5,6,7,8-tetra-
hydro-6-hydroxy-1,6-dimethyl-8-(fur-2-yl)isoquinoline-
4-carbonitrile IIIа was confirmed by the experiment of
homonuclear Overhauser effect. On selective irra-
diating the methyl group in the position 1 of iso-
quinoline, the interaction with NH-proton was ob-
served, what is impossible in the case of quinoline
formation.
The literature analysis shows that the condensation
of functionally substituted cyclohexanones with cyano
(thio)acetamide proceeds ambiguously. Thus, it was
reported earlier that a mixture of isoquinolines and
quinolines was obtained on the basis of 2-acetylcyclo-
hexanone derivatives [7]. At the same time Ozols et al.
[8] mentioned only isoquinolinethiones as only reac-
tion products.
The reaction of compounds IIIа and IIIb with
alkylating agents IVа–IVc in DMF solution in basic
medium gave rise to the corresponding S-alkyl-
tetrahydroisoquinolines Vа–Vd, whose structure was
confirmed by spectral studies.
To extende the studies on the nitrogen-containing
fused heterocycles [9–11] in this work the reaction of
2,4-diacetyl-5-hydroxy-5-methyl-3-phenyl(heteryl)cyclo-
For unambiguous structure determination of com-
pound Vd we performed X-ray diffraction investiga-
2037

2038
DYACHENKO et al.
NH2
NC
O
R1
O
O
R1
O
O
S
II
NH2
S
_H2O
OH
OH
Iа_Id
CN
A
_H2O
R1
O
R1
O
R2Hlg
IVа_IVc
N
NH
R2
S
S
OH
Vа_Vd
OH
CN
CN
IIIа_IIId
R1 = 3-pyridinyl (Iа, IIIа, Va), 2-furyl (Ib, IIIb, Vb, Vc), 5-methylfur-2-yl (Ic, IIIc), Ph (Id, IIId, Vd); R2Hlg = PhCH2Cl
(IVа), PhC(O)CH2Br (IVb), MeI (IVc); R2 = PhCH2 (Vа), PhC(O)CH2 (Vb), Me (Vc, Vd)
tion (see the figure, Tables 1, 2). In molecule Vd there
are three chiral centers: atoms С1, С2 and С3, which
have relative configurations S-R-S. Cyclohexene ring
is in a semi-chair conformation (folding parameters are
[12]: S 0.60, Θ 34.6°, Ψ 22.1°). Phenyl, acetyl sub-
stituents, and methyl group С18 are equatorially
oriented relative to the cycle, and hydroxy group,
axially [torsion angles C10–C1–C2–C3 –171.82(11)°,
C16–C2–C3–C4 –173.86(12)°, С18C3C2–C1 –174.82(12)°
and О2C3C2C1 –50.72(14)°]. Carbonyl group is oriented
to hydroxy group due to the formation of a weak
intramolecular hydrogen bond O2–H2···O1 [H···O
2.23(2) Å, O–H···O 136(2)°]. In the molecule a
sufficient steric repulsion between methyl С19 and
phenyl groups is observed as evidenced by the strongly
shortened intramolecular contact С10···С19 2.99 Å (sum
C13
C12
C11
C14
C15
C17
C10
C1
C16
C19
C2
C6
C7
O1
N1
C8
C20
C5
C3
C4
C18
C9
C21
N2
S1
O2
General view of molecule Vd.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 10 2010

SYNTHESIS OF 7-ACETYL-2,3,5,6,7,8-HEXAHYDRO-6-HYDROXY-...
Table 1. Bond lengths (d, Å) in the structure Vd
2039
Bond
S1–C8
d
Bond
C1–C10
C1–C6
C1–C2
C2–C16
C2–C3
C3–C4
C3–C18
d
Bond
C4–C5
C5–C6
C5–C9
C6–C7
C7–C19
C8–C9
C9–C21
d
Bond
d
1.7586(13)
1.774(2)
1.5192(18)
1.5247(17)
1.5437(19)
1.5211(19)
1.541(2)
1.495(2)
C10–C11
C10–C15
C11–C12
C12–C13
C13–C14
C14–C15
C16–C17
1.380(2)
1.3838(18)
1.381(2)
1.366(2)
1.361(2)
1.378(2)
1.489(2)
S1–C20
O1–C16
O2–C3
N1–C8
N1–C7
N2–C21
1.3899(18)
1.3985(18)
1.3986(19)
1.4983(18)
1.386(2)
1.2023(19)
1.4268(19)
1.3223(17)
1.3429(16)
1.1321(19)
1.5090(19)
1.521(2)
1.438(2)
Table 2. Bond angles (ω, deg) in the structure Vd
Angle
C8S1C20
C3O2H2
C8N1C7
C10C1C6
C10C1C2
C6C1C2
C16C2C3
C16C2C1
C3C2C1
O2C3C4
O2C3C18
ω
Angle
C4C3C18
O2C3C2
C4C3C2
C18C3C2
C5C4C3
C6C5C9
C6C5C4
C9C5C4
C5C6C7
C5C6C1
C7C6C1
ω
Angle
N1C7C6
N1C7C19
C6C7C19
N1C8C9
N1C8S1
ω
Angle
ω
102.34(8)
108.1(17)
119.08(12)
114.57(11)
108.08(11)
112.34(10)
111.14(12)
109.16(11)
111.78(11)
105.72(12)
110.66(13)
110.15(13)
110.26(12)
107.20(12)
112.56(13)
113.94(11)
118.28(13)
122.64(12)
119.08(12)
117.96(11)
120.82(12)
121.06(11)
122.82(12)
113.17(12)
123.98(11)
121.97(12)
119.07(11)
118.93(11)
119.70(12)
119.29(12)
120.99(14)
118.47(13)
121.23(11)
C15C10C1
C10C11C12
C13C12C11
C14C13C12
C13C14C15
C14C15C10
O1C16C17
O1C16C2
120.26(13)
120.22(13)
120.49(16)
119.94(15)
120.13(15)
120.75(15)
121.70(15)
119.77(15)
118.52(15)
177.98(19)
C9C8S1
C8C9C5
C8C9C21
C5C9C21
C11C10C15
C11C10C1
C17C16C2
N2C21C9
of van der Waals radii is 3.4(2) Å [13]), and also
significant increase in the bond angle values С6C1C10
114.57(11)° and C6–C7–C19 123.98(11)° in comparison
with C2–C1–C10 108.08(11)° and N1–C7–C19 113.17(12)°,
respectively. There is also a shortened intramolecular
contact between acetyl and methyl substituents
С18–H18a···C16 2.67 Å (sum of van der Waals radii is
2.87 Å).
EXPERIMENTAL
The IR spectra were recorded on a FTIR-
spectrometer Spectrum One (Perkin Elmer) in mineral
oil. The Н NMR spectra were registered on a Bruker
1
Avance 400 instrument in DMSO-d6 relative to
internal TMS. The mass spectra were taken on a spec-
trometers МKh-1321 (70 eV) using direct admission of
the substance into the ion source (compounds ІІІd,
Va, Vb) and Crommas GC/MS–Hewlett-Packard
5890/5972, column HP-5 MS (70 eV) in CH2Cl2 (Іа,
Іd, ІІІа–IIIc, Vc, Vd). Melting points were deter-
mined on a Koeffler apparatus. The reaction progress
and purity of the compounds obtained were monitored
with TLC using Silufol UV-254 plates and a mixture
In the crystal intermolecular С–Н···О hydrogen
bonds C20–H20A···O1' [–x, –y, 1 – z] (H···O 2.46 Å,
C–H···O 161°) and C20–H20С···O2' [–1 + x, y, z] (H···O
2.37 Å, C–H···O 163°), are observed, which connect
the molecules into zigzag chains along a axis of the
crystal.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 10 2010

2040
DYACHENKO et al.
acetone-hexane (3:5) as eluent, detecting with iodine
vapor and UV irradiation.
5.22 s (1Н, ОН), 5.90 s (1Н, С3Нfuran), 6.03 d (1Н,
С4Нfuran, J 2.4 Hz). Mass spectrum, m/z (Irel, %): 291
(100) [M – 1]+. Found, %: C 65.77; H 6.99.
C19H20N2O3S. Calculated, %: C 65.74; H 6.90.
X-Ray diffraction analysis of compound Vd was
performed on a Xcalibur-3 four-circle diffractometer
(MoKα radiation, ССD-detector, graphite monochro-
mator, ω-scanning, 2θmax = 55°). The unit cell para-
meters at 298K are as follows: a 8.3439(5) Å,
b 10.2553(7) Å, c 11.90306 Å, α 99.223(5)°, β 108.308(5)°,
γ 91.365(5)°, V 951.4810 Å3, M 366.47, Z 2, space
group P1, dcalc 1.28 g cm–3, μ(MoKα) 0.19 mm–1, F
(000) 388. Intensities of 8342 reflections were
measured (4318 independent, Rint 0.016).
7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-di-
methyl-8-(pyridin-3-yl)-3-thioxoisoqui-noline-4-carbo-
nitrile (IIIа). To a suspension of 2 g (7 mmol) of cyclo-
hexanone Iа in 20 ml of anhydrous ethanol was added
0.7 (7 mmol) of cyanothioacetamide II. The reaction
mixture was stirred for 15 min, and then 0.61 ml
(7 mmol) of morpholine was added. The mixture was
heated to 60оС under stirring and cooled to 15°С. After
24 h the formed precipitate was filtered off and washed
with ethanol. Yield 2.1 g (85%), yellow powder, mp
244–246°С. IR spectrum, ν, cm–1: 3420 (ОН), 3280
(NH), 2226 (C≡N), 1700 (C=O). 1Н NMR spectrum, δ,
ppm: 1.25 s (3Н, Ме), 1.86 s (3Н, Ме), 2.13 s (3Н,
Ме), 2.85–2.90 m (2Н, С5Н and С7Н), 3.22 d (1Н,
The structure was solved by the direct method by
means of SHELXTL program package [14]. Hydrogen
atoms positions were geometrically revealed and
refined in a rider-model with Uiso = nUequiv (n = 1.5 for
methyl groups and n = 1.2 for the other hydrogen
atoms), except for hydroxy hydrogen atom, which was
isotropically refined. The structure was refined by full-
matrix least-squares procedure on F2 in anisotropic
approximation for nonhydrogen atoms to wR2 0.105 by
4318 reflections [R1 0.038 by 2733 reflections with F >
4σ(F), S 1.00]. bonds lengths and bond angles are
given in Tables 1 and 2, respectively. The main crystal-
lographic data were deposited into the Cambridge
Crystallographic Data Center (CCDC 753449).
2
С5Н, J 17.6 Hz), 4.49 d (1Н, С8Н, J 10.4 Hz),
5.05 br.s (1Н, ОН), 7.27–7.29 m (1Н, С5Нpyridine), 7.53
d (1Н, С4Нpyridine, J 7.4 Hz), 8.37–8.41 m (2Н,
С2Нpyridine and С6Нpyridine), 13.80 br.s (1H, NH). Mass
spectrum, m/z (Irel, %): 354 (98) [M + 1]+. Found, %: C
64.43; H 5.37; N 11.78. C19H19N3O2S. Calculated, %:
C 64.57; H 5.42; N 11.89.
7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-di-
methyl-3-thioxo-8-(fur-2-yl)isoquinoline-4-carbo-
nitrile (IIIb) was obtained similarly from cyclo-
hexanone Ib. Yield 1.2 g (97%), yellow powder, mp
261°С. IR spectrum, ν, cm–1: 3427 (ОН), 3270 (NH),
2222 (C≡N), 1701 (C=O). 1Н NMR spectrum, δ, ppm:
1.32 s (3Н, Ме), 2.13 s (3Н, Ме), 2.17 s (3Н, Ме),
2.88 s (2Н, С5Н2), 3.08 d (1Н, С7Н, J 8.04 Hz), 4.51 d
(1Н, С8Н, J 8.04 Hz), 4.89 br.s (1Н, ОН), 6.04 d (1Н,
С3Нfuran, J 3.15 Hz), 6,27 d.d (1Н, С4Нfuran, J 3.06,
1.88 Hz), 7.37 s (1Н, С5Нfuran), 13.74 br.s (1H, NH).
Mass spectrum, m/z (Irel, %): 343 (100) [M + 1]+.
Found, %: C 63.07; H 5.21; N 8.11. C18H18N2O3S.
Calculated, %: C 63.14; H 5.30; N 8.18.
2,4-Diacetyl-5-hydroxy-5-methyl-3-phenyl(heteryl)-
cyclohexanones (Iа–Id) were obtained by the known
procedure [15].
2,4-Diacetyl-5-hydroxy-5-methyl-3-(pyridin-3-yl)-
cyclohexanone (Iа). Yield 2.5 g (87%), white powder,
mp 175°С. IR spectrum, ν, cm–1: 3421 (ОН), 1709
1
(C=O). Н NMR spectrum, δ, ppm: 1.19 s (3Н, Ме),
1.91 s (3Н, Ме), 1.92 s (3Н, Ме), 2.37 d (1Н, С4Н, J
10.8 Hz), 2.33–3.36 m (2Н, С6Н2), 3.97–4.02 m (1Н,
С3Н), 4.18 d (1Н, С2Н, J 9.6 Hz), 5.30 s (1Н, ОН),
7.29–7.31 m (1Н, С5Нpyridine), 7.79 d (1Н, С4Нpyridine, J
6.0 Hz), 8.37–8.40 m (1Н, С6Нpyridine), 8.50 s (1H,
С2Нpyridine). Mass spectrum, m/z (Irel, %): 290 (100)
[M + 1]+. Found, %: C 66.40; H 6.67; N 4.81.
C19H19N3O2S. Calculated, %: C 66.42; H 6.62; N 4.84.
7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-di-
methyl-8-(5-methylfur-2-yl)-3-thioxoisoquinoline-4-
carbonitrile (IIIc) was obtained similarly from cyclo-
hexanone Ic. Yield 3.15 g (88%), yellow powder, mp
220°С. IR spectrum, ν, cm–1: 3437 (ОН), 3270 (NH),
2217 (C≡N), 1704 (C=O). 1Н NMR spectrum, δ, ppm:
1.06 s (3Н, Ме), 1.29 s (3Н, Ме), 2.14 s (3Н, Ме),
2,4-Diacetyl-5-hydroxy-5-methyl-3-(5-methylfur-
2-yl)cyclohexanone (Ic). Yield 3.15 g (85%), white
powder, mp 125–127°С. IR spectrum, ν, cm–1:
1
3430 (ОН), 1704 (C=O). Н NMR spectrum, δ, ppm:
1.17 s (3Н, Ме), 2.04 s (3Н, Ме), 2.07 s (3Н, Ме),
2
2.17 s (3Н, Ме), 2.83 d (1Н, С5Н, J 16.0 Hz), 3.01–
2.17 s (3Н, Ме), 2.31 d (1Н, С4Н, J 10.8 Hz), 2.89 d
2
(1Н, С2Н, J 10.8 Hz), 3.15 d (1Н, С6Н2, J 9.2 Hz),
3.08 m (2Н, С5Н and С7Н), 4.51 d (1Н, С8Н, J 8.04 Hz),
3.99 d (1Н, С6Н2, J 9.6 Hz), 4.04–4.09 m (1Н, С3Н),
5.05 br.s (1Н, ОН), 5.96 d (2Н, С3Нfuran and С4Нfuran
,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 10 2010

SYNTHESIS OF 7-ACETYL-2,3,5,6,7,8-HEXAHYDRO-6-HYDROXY-...
2041
J 16.00 Hz), 13.86 br.s (1H, NH). Mass spectrum, m/z
(Irel, %): 357 (100) [M + 1]+. Found, %: C 64.03;
H 5.51; N 7.83. C19H20N2O3S. Calculated, %: C 64.02;
H 5.66; N 7.86.
N 6.01. C26H24N2O4S. Calculated, %: C 67.81; H 5.25;
N 6.08.
7-Acetyl-5,6,7,8-tetrahydro-6-hydroxy-1,6-dime-
thyl-3-methylthio-8-(fur-2-yl)isoquinoline-4-carbo-
nitrile (Vc) was obtained similarly from isoquinoline
IIIb and methyl iodide IVc. Yield 0.4 g (75%), white
powder, mp 160°С. IR spectrum, ν, cm–1: 3478 (ОН),
2220 (C≡N), 1706 (C=O). 1Н NMR spectrum, δ, ppm:
1.26 s (3Н, Ме), 2.14 s (3Н, Ме), 2.20 s (3Н, Ме),
2.56 s (3Н, Ме), 2.82 d (1Н, С5Н, 2J 17.27 Hz), 3.03–
3.12 m (2Н, С5Н and С7Н), 4.70 d (1Н, С8Н, J 9.25 Hz),
5.00 br.s (1Н, ОН), 6.10 d (1Н, С3Нfuran, J 3.14 Hz),
6,35 d. d (1Н, С4Нfuran, J 2.95 Hz, J 1.90 Hz), 7.51 s
(1Н, С5Нfuran). Mass spectrum, m/z (Irel, %): 357 (100)
[M + 1]+. Found, %: C 63.94; H 5.52; N 7.76.
C19H20N2O3S. Calculated, %: C 64.02; H 5.66; N 7.86.
7-Acetyl-2,3,5,6,7,8-hexahydro-6-hydroxy-1,6-di-
methyl-3-thioxo-8-phenylisoquinoline-4-carbonitrile
(IIId) was obtained similarly from cyclohexanone Id.
Yield 0.57 g (88%), yellow powder, mp 266–268°С
(published data [8] 269–270°С). Mass spectrum, m/z
(Irel, %): 352 (2) [M]+, 334 (5.9) [M – Н2О]+, 291 (100),
251 (4.1), 215 (10), 128 (3.1), 77 (6.6) [Ph]+, 43 (84.7).
7-Acetyl-3-benzylthio-5,6,7,8-tetrahydro-6-hyd-
roxy-1,6-dimethyl-8-(pyridin-3-yl)isoquinoline-4-
carbonitrile (Vа). To a solution of 0.5 g (1.4 mmol) of
compound IIIа in 5 ml of DMF was added 0.16 ml
(1.4 mmol) of benzyl chloride IVа, and then 0.78 ml
(14 mmol) of 10% KОН solution. This mixture was
stirred at heating to 50°С for 30 min. After 48 h the
formed precipitate was filtered off and washed with
ethanol. Yield 0.51 g (81%), grey powder, mp 240°С
(МеОН). IR spectrum, ν, cm–1: 3435 (ОН),
2214 (C≡N), 1709 (C=O). 1Н NMR spectrum, δ, ppm:
1.00 s (3Н, Ме), 1.95 s (3Н, Ме), 1.97 s (3Н, Ме),
7-Acetyl-5,6,7,8-tetrahydro-6-hydroxy-1,6-dime-
thyl-3-methylthio-8-phenylisoquinoline-4-carbo-
nitrile (Vd) was obtained similarly from isoquinoline
IIId and methyl iodide IVc. Yield 1.2 g (73%),
colorless crystals, mp 198°С (published data [8] 200–
201°С). Mass spectrum, m/z (Irel, %): 367 (100) [M + 1]+.
2
2.88 d (1Н, С5Н, J 16.88 Hz), 3.28–3.30 m (2Н, С5Н
REFERENCES
and С7Н), 4.39–4.50 m (3Н, С8Н and SCH2), 5.44 br.s
(1Н, ОН), 7.20–7.30 m (4Н, НAr), 7.38–7.43 m (3Н,
НAr), 8.26 d (1Н, С2Нpyridine, J 1.78 Hz), 8.42 d (1Н,
С6Нpyridine, J 3.66 Hz). Mass spectrum, m/z (Irel, %):
443 (29.2) [M]+, 400 (21.7), 350 (2.8), 305 (3.6),
220 (1.4), 206 (1.5), 140 (2.0), 91 (100) [PhCH2]+, 43
(59.8). Found, %: C 70.29; H 5.61; N 9.36.
C26H25N3O2S. Calculated, %: C 70.40; H 5.68; N 9.47.
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7-Acetyl-3-benzoylthio-5,6,7,8-tetrahydro-6-hyd-
roxy-1,6-dimethyl-8-(fur-2-yl)isoquinoline-4-carbo-
nitrile (Vb) was obtained similarly from isoquinoline
IIIb and phenacylbromide IVb. Yield 0.3 g (44%),
yellow powder, mp 262–265°С (DMF). IR spectrum,
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1
ν, cm–1: 3446 (ОН), 2219 (C≡N), 1704 (C=O). Н
NMR spectrum, δ, ppm: 1.32 s (3Н, Ме), 2.15 s (3Н,
Ме), 2.24 s (3Н, Ме), 3.01 d (1Н, С7Н, J 9.93 Hz),
7. Kaiho, T., San-Nohe, K., Kajiya, S., Suzuki, T., Otsuka, K.,
Ito, T., Kamiya, J., and Maruyama, M., J. Med. Chem.,
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2
2
3.30 d (1Н, С5Н, J 17.92 Hz), 3.52 d (1Н, С5Н, J
17.42 Hz), 4.79 d (1Н, С8Н, J 9.89 Hz), 4.91 br.s (1Н,
ОН), 6.06 d (1Н, С3Нfuran, J 2.77 Hz), 6.35 s (1Н,
С4Нfuran), 7.49–7.58 m (4Н, НAr), 7.74 d (2Н, НAr,
J 7.17 Hz), 8.15 s (2Н, SCH2). Mass spectrum, m/z
(Irel, %): 460 (32.8) [M]+, 442 (26.6), 399 (59.7), 385
(23), 331 (5.8), 307 (6.8), 251 (2.9), 153 (2.5), 105
(100), 77 (63.5), 43 (55.6). Found, %: C 67.72; H 5.15;
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