Synthesis of 4-aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles by three-component condensation of aromatic aldehydes with cyanothioacetamide and 4,4,4-trifluoro-1-phenylbutane-1,3-dione

Article abstract of DOI:10.1134/S1070428011100150

4-Aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles were synthesized by three-component condensation of aromatic aldehydes with cyanothioacetamide and 4,4,4-trifluoro-1-phenylbutane-1,3- dione. The reaction involved initial formation of Michael adducts which underwent acyl cleavage. Pleiades Publishing, Ltd., 2011.

Full text of DOI:10.1134/S1070428011100150

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 10, pp. 1535–1539. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.D. Dyachenko, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 10, pp. 1508–1511.
Synthesis of 4-Aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-
3-carbonitriles by Three-Component Condensation
of Aromatic Aldehydes with Cyanothioacetamide
and 4,4,4-Trifluoro-1-phenylbutane-1,3-dione
V. D. Dyachenko
Taras Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011 Ukraine
e-mail: dvd_lug@online.lg.ua
Received February 24, 2011
Abstract—4-Aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles were synthesized by three-com-
ponent condensation of aromatic aldehydes with cyanothioacetamide and 4,4,4-trifluoro-1-phenylbutane-1,3-
dione. The reaction involved initial formation of Michael adducts which underwent acyl cleavage.
DOI: 10.1134/S1070428011100150
As shown previously, 3-aryl-2-cyanoprop-2-ene-
thioamides react with 4,4,4-trifluoro-1-phenylbutane-
1,3-dione according to the Michael addition pattern,
and the subsequent acyl cleavage of the Michael ad-
duct yields 4-aryl-6-phenyl-2-thioxo-1,2-dihydropyri-
dine-3-carbonitriles [1]. 1-(2-Thienyl)-4,4,4-trifluoro-
butane-1,3-dione behaved similarly in analogous
Michael reaction [2].
and IVb was confirmed by their independent synthesis
by reaction of chalcones Va and Vb with cyanothio-
acetamide (II) (method b) and by alkylation with alkyl
halides VI–VIII to obtain the corresponding sulfides
IX–XI (Scheme 1).
The IR spectra of compounds IX–XI contained
absorption bands typical of stretching vibrations of
conjugated cyano group (2218–2227 cm–1). 2-Thioxo-
1,2-dihydropyridine-3-carbonitriles IX–XI displayed
The present communication reports on three-com-
ponent condensation of aromatic aldehydes Ia and Ib
with cyanothioacetamide (II) and 4,4,4-trifluoro-1-
phenylbutane-1,3-dione (III). The reactions were
carried out in ethanol at 20°C in the presence of
N-methylmorpholine as catalyst (method a), and the
products were 4-aryl-6-phenyl-2-thioxo-1,2-dihydro-
pyridine-3-carbonitriles IVa and IVb (Scheme 1)
which attract interest as promising intermediate prod-
ucts for the synthesis of antibacterial [3], analgesic [4],
and cardiotonic agents [5], as well as of inhibitors of
some enzymes [6].
1
in the H NMR spectra signals from protons in the
aromatic substituents, 5-H in the pyridine ring, protons
in fragment Z, and methylene protons in the SCH2
group (δ 2.76–5.84 ppm (see Experimental). In the
mass spectra of IX–XI low-intense peaks from
[M + 2]+ ions were observed, which indicated the pres-
ence of sulfur in their molecules [9].
EXPERIMENTAL
The IR spectra were recorded on an IKS-40 spec-
trometer from samples dispersed in mineral oil. The
1H NMR spectra were obtained on a Bruker AM-300
spectrometer at 300.13 MHz from solutions in
DMSO-d6 using tetramethylsilane as internal refer-
ence. The mass spectra (electron impact, 70 eV) were
recorded on a Kratos MS-890 instrument with direct
sample admission into the ion source. The melting
points were determined on a Kofler hot stage. The
progress of reactions and the purity of products were
monitored by TLC on Silufol UV-254 plates using
Presumably, the process includes initial formation
of Knoevenagel condensation products A, followed by
Michael addition of cyanothioacetamide (II). Adduct B
thus formed takes up ethanol molecules to produce
structure C which undergoes acyl cleavage with elimi-
nation of ethyl trifluoroacetate [7], and the subsequent
intramolecular heterocyclization is accompanied by
elimination of water and dehydrogenation. In addition
to spectral data [8], the structure of compounds IVa
1535

DYACHENKO
1536
Scheme 1.
S
S
O
O
N-Methylmorpholine
CN
Ar
H2N
Path a:
ArCHO
+
+
CN
–H2O
H2N
Ar
F3C
Ph
Ar
Ia, Ib
II
III
EtO OH
F3C
Ph
A
O
Ar
CN
S
CN
CN
S
EtOH
F3C
Ph
III
–CF3COOEt
–2[H], –H2O
S
Ph
N
H
O
NH2
O
NH2
B
C
IVa, IVb
O
II, MeONa
–2[H], –H2O
Path b:
IVa, IVb
Ph
Ar
Va, Vb
PhCH(Cl)CONH2 (VII)
KOH
MeO
Ph
CN
Ph
NH2
N
S
Ar
HlgCH2Z (VIa–VIn)
KOH
O
CN
X
IVa, IVb
Ph
N
S
Z
MeO
Ph
IXa–IXn
Br(CH2)4Br (VIII)
KOH
Ph
OMe
N
N
S
CN
CN
S
XI
I, IV, V, Ar = 4-O2NC6H4 (a), 2-MeOC6H4 (b); VI, Hlg = Br: Z = 2-MeC6H4CO (a), 2-oxo-2H-chromen-3-ylcarbonyl (b),
CH2=CHCH2 (c), Et (i), 3,4-Cl2C6H3 (l), 4-BrC6H4CO (m); Hlg = I: Z = Me(CH2)10 (d), H (j); Hlg = Cl: Z = PhNHCO (e),
naphthalen-1-ylcarbamoyl (f), HOCO (g), H2NCO (h), Ph (k), EtOCO (n); IX, Ar = 4-O2NC6H4, Z = 2-MeC6H4CO (a); Ar =
2-MeOC6H4: Z = 2-oxo-2H-chromen-3-ylcarbonyl (b), CH2=CHCH2 (c), Me(CH2)10 (d), PhNHCO (e), naphthalen-1-ylcarbamoyl (f),
HOCO (g), H2NCO (h), Et (i), H (j), Ph (k), 3,4-Cl2C6H3 (l), 4-BrC6H4CO (m), EtOCO (n).
acetone–hexane (3:5) as eluent; spots were visualized
by treatment with iodine vapor or under UV light.
for 2 h, left to stand for 48 h, diluted with 10% hydro-
chloric acid to pH 5, and left to stand for 24 h. The
precipitate was filtered off, washed with ethanol and
hexane, and recrystallized from glacial acetic acid.
Yield 2.26 g (68%), mp 225–227°C; published data
[8]: mp 226–228°C.
4-(4-Nitrophenyl)-6-phenyl-2-thioxo-1,2-dihy-
dropyridine-3-carbonitrile (IVa). a. Three drops of
N-methylmorpholine were added at 20°C under stir-
ring to a solution of 10 mmol of 4-nitrobenzaldehyde
(Ia) and 1.0 g (10 mmol) of cyanothioacetamide (II) in
25 ml of ethanol. The mixture was stirred for 15 min,
1.54 ml (10 mmol) of 4,4,4-trifluoro-1-phenylbutane-
1,3-dione (III) and 2.2 ml (20 mmol) of N-methyl-
morpholine were added, and the mixture was stirred
4-(2-Methoxyphenyl)-6-phenyl-2-thioxo-1,2-di-
hydropyridine-3-carbonitrile (IVb) was synthesized
in a similar way. Yield 1.97g (62%), yellow powder,
mp 138–140°C. IR spectrum, ν, cm–1: 3380 (NH),
1
2228 (C≡N). H NMR spectrum, δ, ppm: 3.84 s (3H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011

SYNTHESIS OF 4-ARYL-6-PHENYL-2-THIOXO-1,2-DIHYDROPYRIDINE-3-CARBONITRILES
1537
Me), 7.08 s (1H, 5-H), 7.12 t (1H, Harom, J = 8.1 Hz),
7.23 d (1H, Harom, J = 8.7 Hz), 7.39–7.63 m (5H,
7.84 s (1H, 5-H), 8.25 m (2H, Harom). Found, %:
C 73.68; H 4.95; N 7.66. C22H18N2OS. Calculated, %:
C 73.72; H 5.06; N 7.81.
H
H
arom), 7.84 d (1H, Harom, J = 8.1 Hz), 8.03 m (1H,
arom), 14.23 br.s (1H, NH). Found, %: C 71.52;
2-Dodecylsulfanyl-4-(2-methoxyphenyl)-6-phe-
nylpyridine-3-carbonitrile (IXd). Yield 3.21 g (66%),
mp 55–56°C (from MeOH). IR spectrum: ν 2226 cm–1
(C≡N). 1H NMR spectrum, δ, ppm: 0.87 t (3H, Me, J =
6.5 Hz), 1.18–1.62 m (18H, CH2), 1.81 m (2H, CH2),
3.36 t (2H, SCH2, J = 7.24 Hz), 3.85 s (3H, MeO),
7.12 t (2H, Harom, J = 7.32 Hz), 7.31 d (1H, Harom, J =
7.32 Hz), 7.43–7.53 m (4H, Harom), 7.61 s (4H, 5-H),
8.15 m (2H, Harom). Mass spectrum, m/z (Irel, %): 488
(2) [M + 2]+, 487 (19) [M + 1]+, 486 (63) [M]+, 485
(51) [M – H]+, 471 (92) [M – Me]+, 455 (54), 318 (87),
301 (62), 287 (22), 214 (10), 57 (36), 43 (100). Found,
%: C 76.38; H 7.75; N 5.60. C31H38N2OS. Calculated,
%: C 76.50; H 7.87; N 5.76. M 486.7.
H 4.29; N 8.71. C19H14N2OS. Calculated, %: C 71.68;
H 4.43; N 8.80.
Method b was described previously [8]; yield of
IVa 70%, yield of IVb 66%.
4-Aryl-2-Z-methylsulfanyl-6-phenylpyridine-3-
carbonitriles IXa–IXn (general procedure). Pyridine-
2-thione IVa or IVb, 10 mmol, was dissolved in 15 ml
of DMF, and 5.6 ml (10 mmol) of a 10% aqueous
solution of potassium hydroxide and 10 mmol of halo-
gen derivative VIa–VIn were added in succession.
The mixture was stirred for 4 h and diluted with
an equal volume of water, and the precipitate was fil-
tered off and washed with water, ethanol, and hexane.
[3-Cyano-4-(2-methoxyphenyl)-6-phenylpyridin-
2-ylsulfanyl]-N-phenylacetamide (IXe). Yield 3.2 g
(71%), mp 185–187°C (from BuOH). IR spectrum, ν,
2-(2-Methylbenzoylmethylsulfanyl)-4-(4-nitro-
phenyl)-6-phenylpyridine-3-carbonitrile (IXa).
Yield 3.44 g (74%), yellow powder, mp 171–173°C
(from AcOH). IR spectrum, ν, cm–1: 2225 (C≡N), 1711
1
cm–1: 3332 (NH), 2220 (C≡N), 1671 (C=O). H NMR
1
spectrum, δ, ppm: 3.83 s (3H, Me), 4.23 s (2H, CH2),
6.97–7.63 m (13H, Harom), 8.08 d (2H, Harom, J =
7.82 Hz), 10.24 br.s (1H, NH). Mass spectrum, m/z
(Irel, %): 453 (2) [M + 2]+, 452 (8) [M + 1]+, 451 (25)
[M]+, 436 (10) [M – Me]+, 359 (92) [M – PhNH]+, 331
(100) [PhNHCO]+, 317 (86), 301 (89), 132 (22), 93
(28) [PhNH2]+, 77 (29) [Ph]+, 65 (26), 39 (7). Found,
%: C 71.72; H 4.50; N 9.22. C27H21N3O2S. Calculated,
%: C 71.82; H 4.69; N 9.31. M 451.6.
(C=O). NMR spectrum N, δ, ppm: 2.98 s (3H, Me),
4.96 s (2H, CH2), 7.19 t (2H, Harom, J = 7.14 Hz),
7.34 t (1H, Harom, J = 6.72 Hz), 7.55 t (2H, Harom, J =
7.24 Hz), 7.65 t (1H, Harom, J = 6.72 Hz), 7.81 s (1H,
5-H), 7.85 d (2H, Harom, J = 8.08 Hz), 7.98 d (2H,
Harom, J = 8.68 Hz), 8.11 d (2H, Harom, J = 7.36 Hz),
8.39 d (2H, Harom, J = 8.68 Hz). Mass spectrum, m/z
(Irel, %): 451 (49) [M – Me]+, 434 (18), 346 (62) [M –
Me – C6H5CO]+, 330 (40), 300 (15), 227 (19), 105
(100) [C6H5CO]+, 91 (4) [PhCH2]+, 77 (38) [Ph]+, 51
(5). Found, %: C 69.50; H 4.02; N 8.95. C27H19N3O3S.
Calculated, %: C 69.66; H 4.11; N 9.03. M 465.5.
[3-Cyano-4-(2-methoxyphenyl)-6-phenylpyridin-
2-ylsulfanyl]-N-(naphthalen-1-yl)acetamide (IXf).
Yield 3.46 g (69%), mp 225–227°C (from DMF). IR
spectrum, ν, cm–1: 3341 (NH), 2227 (C≡N), 1666
4-(2-Methoxyphenyl)-2-(2-oxo-2H-chromen-3-yl-
carbonylmethylsulfanyl)-6-phenylpyridine-3-carbo-
nitrile (ІXb). Yield 3.93 g (78%), colorless crystals,
mp 192–194°C (from BuOH). IR spectrum, ν, cm–1:
2228 (C≡N); 1714, 1695 (C=O). 1H NMR spectrum, δ,
ppm: 3.82 s (3H, Me), 5.01 s (2H, CH2), 7.02–7.61 m
(10H, Harom), 7.72–8.12 m (4H, Harom), 8.69 s (1H,
4′-H). Found, %: C 71.35; H 3.88; N 5.39.
C30H20N2O4S. Calculated, %: C 71.41; H 4.00; N 5.55.
1
(C=O). H NMR spectrum, δ, ppm: 3.87 s (3H, Me),
4.42 s (2H, CH2), 7.07–7.18 m (2H, Harom), 7.30–
7.54 m (8H, Harom), 7.65 d (1H, Harom, J = 7.48 Hz),
7.68 s (1H, 5-H), 7.75 d (1H, Harom, J = 7.58 Hz),
7.84 d (1H, Harom, J = 8.02 Hz), 8.08 d (1H, Harom, J =
8.0 Hz), 8.21 d (1H, Harom, J = 7.38 Hz), 10.19 br.s
(1H, NH). Mass spectrum, m/z (Irel, %): 501 (3) [M +
1]+, 501 (19) [M]+, 359 (100) [M – C10H8N]+, 331 (85),
31 (68), 301 (57), 287 (12), 183 (32), 143 (95)
[1-aminonaphthalene]+, 115 (91), 43 (6). Found, %:
C 74.11; H 4.58; N 8.29. C31H23N3O2S. Calculated, %:
C 74.23; H 4.62; N 8.38. M 501.6.
2-Allylsulfanyl-4-(2-methoxyphenyl)-6-phenyl-
pyridine-3-carbonitrile (IXc). Yield 2.83 g (79%),
mp 88–89°C (from BuOH). IR spectrum: ν 2222 cm–1
1
(C≡N). H NMR spectrum, δ, ppm: 3.81 s (3H, Me),
4.11 d (2H, SCH2, J = 6.57 Hz), 5.21 d (1H, =CH2,
Jcis = 9.55 Hz), 5.47 d (1H, =CH2, Jtrans = 17.3 Hz),
5.81–6.22 m (1H, CH=), 7.02–7.69 m (7H, Harom),
[3-Cyano-4-(2-methoxyphenyl)-6-phenylpyridin-
2-ylsulfanyl]acetic acid (IXg). Yield 2.86 g (76%),
mp 160–162°C (from AcOH). IR spectrum, ν, cm–1:
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011

DYACHENKO
1538
2217 (C≡N), 1720 (C=O). 1H NMR spectrum, δ, ppm:
3.83 s (3H, Me), 4.18 s (2H, CH2), 7.02–7.35 m (3H,
Harom), 7.49–7.61 m (4H, Harom), 7.80 s (1H, 5-H),
8.23 m (2H, Harom), 12.96 br.s (1H, OH). Found, %:
C 66.89; H 4.05; N 7.30. C21H16N2O3S. Calculated, %:
C 67.01; H 4.28; N 7.44.
C 64.03; H 3.44; N 5.39. C27H18Cl2N2O2S. Calculated,
%: C 64.16; H 3.59; N 5.54.
2-(4-Bromobenzoylmethylsulfanyl)-4-(2-me-
thoxyphenyl)-6-phenylpyridine-3-carbonitrile
(IXm). Yield 4.17 g (81%), mp 159–161°C (from
BuOH). IR spectrum, ν, cm–1: 2224 (C≡N), 1714
1
(C=O). H NMR spectrum, δ, ppm: 3.83 s (3H, Me),
[3-Cyano-4-(2-methoxyphenyl)-6-phenylpyridin-
2-ylsulfanyl]acetamide (IXh). Yield 2.63 g (70%),
mp 203–209°C (from BuOH). IR spectrum, ν, cm–1:
3298 (NH2), 2225 (C≡N), 1672 (C=O). 1H NMR spec-
trum, δ, ppm: 3.82 s (3H, Me), 4.10 s (2H, CH2), 7.05–
7.61 m (8H, Harom, NH2), 7.76 br.s (1H, NH2), 7.84 s
(1H, 5-H), 8.29 m (2H, Harom). Found, %: C 67.03;
H 4.41; N 11.05. C21H17N3O2S. Calculated, %:
C 67.18; H 4.56; N 11.19.
5.03 s (2H, CH2), 7.04–7.69 m (8H, Harom), 7.81 d (4H,
H
arom, J = 7.8 Hz), 8.08 d (2H, Harom, J = 7.04 Hz).
Found, %: C 62.83; H 3.61; N 5.33. C27H19BrN2O2S.
Calculated, %: C 62.92; H 3.72; N 5.44.
Ethyl [3-cyano-4-(2-methoxyphenyl)-6-phenyl-
pyridin-2-ylsulfanyl]acetate (IXn). Yield 3.15 g
(78%), mp 170–172°C (from EtOH). IR spectrum, ν,
cm–1: 2219 (C≡N), 1715 (C=O). 1H NMR spectrum, δ,
ppm: 1.18 t (3H, Me, J = 6.18 Hz), 3.82 s (3H, MeO),
4.11 q (2H, OCH2, J = 6.18 Hz), 4.26 s (2H, SCH2),
7.03–7.63 m (7H, Harom), 7.87 s (1H, 5-H), 8.20 m
(2H, Harom). Found, %: C 68.19; H 4.78; N 6.88.
C23H20N2O3S. Calculated, %: C 68.30; H 4.98; N 6.93.
4-(2-Methoxyphenyl)-6-phenyl-2-propylsulfanyl-
pyridine-3-carbonitrile (IXi). Yield 2.45 g (68%),
mp 101–103°C (from MeOH). IR spectrum:
ν 2219 cm–1 (C≡N). 1H NMR spectrum, δ, ppm: 1.05 t
(3H, Me, J = 7.11 Hz), 1.78 m (2H, CH2), 3.28 t (2H,
SCH2, J = 7.19 Hz), 3.81 s (3H, MeO), 7.05–7.64 m
(7H, Harom), 7.81 s (1H, 5-H), 8.22 m (2H, Harom).
Found, %: C 73.18; H 5.42; N 7.60. C22H20N2OS. Cal-
culated, %: C 73.30; H 5.59; N 7.77.
[3-Cyano-4-(2-methoxyphenyl)-6-phenylpyridin-
2-ylsulfanyl]phenylacetamide (X) was synthesized as
described for compounds IX from 3.18 g (10 mmol) of
pyridinethione IVb and 1.7 g (10 mmol) of chloro-
(phenyl)acetamide (VII). Yield 3.07 g (68%), mp 240–
244°C (from BuOH) (sublimes at 210°C). IR spec-
4-(2-Methoxyphenyl)-2-methylsulfanyl-6-phenyl-
pyridine-3-carbonitrile (IXj). Yield 2.49 g (75%),
mp 143–145°C (from BuOH). IR spectrum:
ν 2220 cm–1 (C≡N). 1H NMR spectrum, δ, ppm: 2.76 s
(3H, MeS), 3.81 s (3H, MeO), 7.02–7.68 m (7H,
Harom), 7.83 s (1H, 5-H), 8.27 m (2H, Harom). Found, %:
C 72.12; H 4.71; N 8.34. C20H16N2OS. Calculated, %:
C 72.26; H 4.85; N 8.43.
1
trum, ν, cm–1: 2225 (C≡N), 1668 (C=O). H NMR
spectrum, δ, ppm: 3.81 s (3H, Me), 5.84 s (1H, SCH),
7.02–7.73 m (13H, Harom, NH2), 7.83 s (1H, 5-H),
8.05 br.s (1H, NH2), 8.28 m (2H, Harom). Found, %:
C 71.69; H 4.58; N 9.22. C27H21N3O2S. Calculated, %:
C 71.82; H 4.69; N 9.31.
2,2′-(Butane-1,4-diylbissulfanyl)bis[(2-methoxy-
phenyl)-6-phenylpyridine-3-carbonitrile] (XI) was
synthesized as described for compounds IX from
3.18 g (10 mmol) of pyridinethione IVb and 0.59 ml
(5 mmol) of 1,4-dibromobutane (VIII). Yield 1.51 g
(48%), mp 188–189°C (from MeCN). IR spectrum:
2-Benzylsulfanyl-4-(2-methoxyphenyl)-6-phenyl-
pyridine-3-carbonitrile (IXk). Yield 3.0 g (74%),
mp 135–137°C (from EtOH). IR spectrum: ν 2226 cm–1
1
(C≡N). H NMR spectrum, δ, ppm: 3.86 s (3H, Me),
4.60 s (2H, CH2), 7.05–7.16 m (2H, Harom), 7.23–
7.34 m (4H, Harom), 7.41–7.5 m (6H, Harom), 7.63 s (1H,
5-H), 8.12 m (2H, Harom). Found, %: C 76.31; H 4.80;
N 6.75. C26H20N2OS. Calculated, %: C 76.44; H 4.94;
N 6.86.
1
ν 2228 cm–1 (C≡N). H NMR spectrum, δ, ppm:
2.01 m (4H, CH2), 3.46 m (4H, SCH2), 3.81 s (6H,
OMe), 6.95–7.68 m (14H, Harom), 7.79 s (2H, 5-H),
8.18 m (4H, Harom). Found, %: C 80.14; H 4.03;
N 8.82. C42H26N4O2S2. Calculated, %: C 80.22;
H 4.17; N 8.91.
2-(3,4-Dichlorobenzoylmethylsulfanyl)-4-(2-me-
thoxyphenyl)-6-phenylpyridine-3-carbonitrile (IXl).
Yield 3.48 g (69%), mp 151–153°C (from AcOH). IR
spectrum, ν, cm–1: 2222 (C≡N), 1712 (C=O). 1H NMR
spectrum, δ, ppm: 3.82 s (3H, Me), 5.05 s (2H, CH2),
7.01–7.62 m (6H, Harom), 7.74–7.86 m (4H, Harom),
8.02 d (1H, Harom, J = 6.95 Hz), 8.12 d (1H, Harom, J =
6.95 Hz), 8.34 d (1H, Harom, J = 7.14 Hz). Found, %:
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nin, Yu.A., and Promonenkov, V.K., Khim. Geterotsikl.
Soedin., 1981, p. 377.
9. Structure Determination of Organic Compounds: Tables
of Spectral Data, Pretsch, E., Bühlmann, P., and
Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed.
Translated under the title Opredelenie stroeniya orga-
nicheskikh soedinenii. Tablitsy spektral’nykh dannykh,
Moscow: Mir, 2006, p. 35.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011