Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl) benzimidoyl]-1,4-benzoquinone imines

Article abstract of DOI:10.1134/S1070428009030105

Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-

Full text of DOI:10.1134/S1070428009030105

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 3, pp. 408–416. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.P. Avdeenko, V.V. Pirozhenko, S.A. Konovalova, D.A. Roman’kov, G.V. Palamarchuk, O.V. Shishkin, 2009, published in Zhurnal
Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 419–426.
Thiocyanation of N-Arylsulfonyl-, N-Aroyl-,
and N-[(N-Arylsulfonyl)benzimidoyl]-1,4-benzoquinone Imines
A. P. Avdeenkoa, V. V. Pirozhenkob, S. A. Konovalovaa, D. A. Roman’kova,
G. V. Palamarchukc, and O. V. Shishkinc
a Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 84313 Ukraine
e-mail: chimist@dgma.donetsk.ua
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine
c Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar’kov, Ukraine
Received July 1, 2008
Abstract—Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-
1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to
give the corresponding N-substituted 5-amino-1,3-benzoxathiol-2-ones as final products.
DOI: 10.1134/S1070428009030105
Thiocyanation of N-substituted para-quinone
imines was the subject of a few publications [1, 2], and
specificity of this reaction remains so far poorly
studied. Thiocyanate ion [NCS]– is a soft ambident
nucleophile possessing two reaction centers, nitrogen
and sulfur atoms. Nucleophilic addition at the nitrogen
atom gives the corresponding isothiocyanates
(–N=C=S), while the addition involving the sulfur
atom produces thiocyanates (–S–C≡N) [3]. The sulfur
atom is known to be a stronger nucleophilic center
than nitrogen. In most cases, addition reactions of thio-
cyanate ion involve the sulfur atom with formation of
thiocyanates [4]. Depending on the product structure
and reaction conditions, isomerization into the corre-
sponding thermodynamically more stable isothiocya-
nate is possible.
The reaction of N-(4-methylphenyl)-1,4-benzoqui-
none imine with potassium and ammonium thiocya-
nates was reported to yield 5-(4-methylphenylamino)-
1,3-benzoxazole-2-thione [1] (Scheme 1). The authors
presumed that the first step in this process is addition
of thiocyanate ion as nitrogen-centered nucleophile at
the ortho position with respect to the carbonyl group.
An indirect support for the proposed reaction path was
opening of the five-membered heteroring in the prod-
uct by the action of lead(IV) oxide as oxidant with
formation of 2-isothiocyanato-N-(4-methylphenyl)-
1,4-benzoquinone imine. Nucleophilic replacement of
the chlorine atom in 2-chloro-N-(4-methylphenyl)-1,4-
benzoquinone imine gave the corresponding thiocy-
anate, N-(4-methylphenyl)-2-thiocyanato-1,4-benzo-
quinone imine, which did not undergo intramolecular
Scheme 1.
H
N
H
N
N
NCS
O
N
PbO2
KSCN
S
O
Me
O
Me
Me
Scheme 2.
NSO2Me
NHSO2Me
SCN
N
S
H2O, Δ
KSCN
NH2
–MeSO3H
MeSO2NH
NSO2Me
NHSO2Me
408

THIOCYANATION OF N-ARYLSULFONYL-, N-AROYL-, ...
409
cyclization [1]. In this case, thiocyanate ion reacted as
sulfur-centered nucleophile. Analogous reaction was
reported for N,N′-bis(methylsulfonyl)-1,4-benzoqui-
none diimine [2]. Here, the product was N,N′-(2-thio-
cyanatobenzene-1,4-diyl)bis(methanesulfonamide)
which was converted into N-(2-amino-1,3-benzothia-
zol-6-yl)sulfonamide upon subsequent aqueous treat-
ment (Scheme 2).
purpose, we examined reactions of thiocyanate ion
with other N-substituted 1,4-benzoquinone imines. We
presumed that convenient substrates could be N-aryl-
sulfonyl-, N-aroyl-, and N-(N-arylsulfonylbenzimid-
oyl)-1,4-benzoquinone imines which are characterized
by high reactivity and relatively high stability. Their
redox potentials are greater than those of N-aryl-1,4-
benzoquinone imines but lower than the corresponding
values of analogous 1,4-benzoquinone diimines.
The formation of N,N′-(2-thiocyanatobenzene-1,4-
diyl)bis(methanesulfonamide) was confirmed by the
IR data, namely by the presence in the IR spectrum of
an absorption band at 2165 cm–1, which is typical of
thiocyanato group. We believe that the cyclization of
N,N′-(2-thiocyanatobenzene-1,4-diyl)bis(methanesul-
fonamide) occurs with participation of water molecule
and elimination of methanesulfonic acid and is accom-
panied by cleavage of the S–N bond in the quinone di-
imine. The latter process is fairly rarely observed in re-
actions of N-sulfonyl-1,4-quinone imines. In particular,
analogous bond cleavage was reported in [5].
The reactions of N-arylsulfonyl-, N-aroyl-, and
N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone
imines Ia–Ij, IIa–IIk, and IIIa–IIIm with potassium
or ammonium thiocyanate were carried out in acetic
acid. To obtain more detailed data, both unsubstituted
quinone imines and those containing alkyl groups (Me,
i-Pr) in different positions of the quinoid ring were
involved. The results showed that most quinone
imines, except for 2,6-disubstituted derivatives, reacted
with thiocyanate ion according to a common scheme to
give N-substituted 5-amino-1,3-benzoxathiol-2-ones
IV–VI. Under the same conditions, 2,6-disubstituted
1,4-benzoquinone imines were reduced to the corre-
sponding aminophenols VII–IX. These findings indi-
cate that the reaction of thiocyanate ion with 1,4-ben-
zoquinone imines is strictly regioselective and that it
follows the 1,4-addition pattern (Scheme 4).
Unsymmetrically substituted 1,4-benzoquinone di-
imines, such as N-tert-butylcarbonyl-N′-methylsul-
fonyl-1,4-benzoquinone diimine and N-methoxycar-
bonyl-N′-methylsulfonyl-1,4-benzoquinone diimine
reacted with thiocyanate ion to give the corresponding
N6-substituted 1,3-benzothiazole-2,6-diamines as
a result of elimination of methylsulfonyl group [2]
(Scheme 3). If a methyl or methoxy group was present
in the meta position with respect to the methylsulfonyl-
imino group, no addition of thiocyanate ion was ob-
served, but the initial quinone diimine was reduced to
the corresponding p-phenylenediamine. This pattern
was rationalized in [2] in terms of steric hindrances.
However, we believe that the R substituent cannot
affect attack by thiocyanate ion on the quinoid ring at
position 5.
N-Substituted 5-amino-1,3-benzoxathiol-2-ones IV–
VI were isolated as colorless crystalline substances.
Their structure was confirmed by elemental analysis
1
and IR and H and 13C NMR spectroscopy. The IR
spectra of IV–VI contained a strong carbonyl absorp-
tion band in the region 1750–1810 cm–1, while bands
typical of initial quinone imines (ν C=O, 1640–
1690 cm–1, and νC=N, 1580–1600 cm–1) were absent.
No signals assignable to NH2 group were observed in
1
the H NMR spectra of IV–VI; this means that the
products are not 2-aminobenzothiazole derivatives like
those described in [2].
Scheme 3.
NX
R
R
The structure of 5-amino-1,3-benzoxathiol-2-ones
IV–VI is also consistent with the 13C NMR spectra
recorded for compounds IVd, IVe, Vb, and Vg). In
particular, the 13C NMR spectrum of IVe lacked sig-
nals from carbonyl and imino carbon atoms (δC 186.1
and 164.7 ppm, respectively, in the spectrum of the
initial quinone imine). The number of signals in the
aromatic region of the spectra of IV and V was larger
by unity, as compared to the initial compounds, while
one CH signal disappeared. In the 13C NMR spectrum
of 3,5-dimethyl-substituted benzoquinone imine Ie,
carbon nuclei in positions 3/5 and 2/6 were magnet-
SCN–, H+
N
S
NH2
XNH
NSO2Me
R = H, Me, MeO; X = t-BuCO. MeOCO.
Taking into account that in the above nucleophilic
addition reactions with various quinone imines thiocy-
anate ion acted as both nitrogen- and sulfur-centered
nucleophile, it was interesting to elucidate factors
determining the reactivity of thiocyanate ion. For this
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 3 2009

AVDEENKO et al.
410
Scheme 4.
R2
R1
6
7
5
7a
HN
X
O
R5
4
2
3a
R2
R1
R3
S
O
IVa–IVh, Va–Vh, VIa–VIk
Me
NCS–
N
O
R5
X
R3
R4
HN
X
OH
Ia–Ij, IIa–IIk, IIIa–IIIm
R5
Me
VIIi, VIIj, VIIIi–VIIIk, IXl, IXm
I, IV, VII, X = SO2, R1 = R2 = R3 = R4 = H (a); R1 = Me, R2 = R3 = R4 = H (b); R1 = R3 = Me, R2 = R4 = H (c, d); R1 = R4 = H, R2 =
R3 = Me (e, f); R1 = R2 = Me, R3 = R4 = H (g, h); R1 = R4 = Me, R2 = R3 = H (i, j); R5 = Me (a, c, e, h, i), H (b, g), MeO (d), Cl (f, j);
II, V, VIII, X = CO, R1 = R3 = Me, R2 = R4 = H (a–c); R1 = R4 = H, R2 = R3 = Me (d–f); R1 = R2 = Me, R3 = R4 = H (g, h); R1 =
R4 = Me, R2 = R3 = H (i–k); R5 = Me (a, d, g, i), MeO (b, e, j), Cl (c, f, h, k); III, VI, IX, X = C(=NSO2Ar), Ar = 4-MeOC6H4 (a, j),
4-MeC6H4 (b, d–g, i, l), Ar = Ph (c), 4-ClC6H4 (h, k, m); R1 = R2 = R3 = R4 = H (a); R1 = Me, R2 = R3 = R4 = H (b); R1 = R3 = Me,
R2 = R4 = H (c, d); R1 = i-Pr, R2 = R4 = H, R3 = Me (e); R1 = Me, R2 = R4 = H, R3 = i-Pr (f); R1 = R4 = H, R2 = R3 = Me (g, h); R1 =
R2 = Me, R3 = R4 = H (i–k); R1 = R4 = Me, R2 = R3 = H (l, m); R5 = H.
ically equivalent due to fast (on the NMR time scale)
Z–E isomerization, whereas compound IVe displayed
separate signals from the above carbon atoms. These
data indicate aromatization of the quinoid fragment
and addition of a carbon-containing substituent to posi-
tion 2(6) of the quinoid ring. The chemical shifts of
carbon nuclei in the arylsulfonyl fragment remain al-
most the same as in the spectrum of initial 1,4-benzo-
quinone imine Ie (δC, ppm: Ie: 139.44, 126.56, 129.53,
143.69; IVe: 138.60, 126.58, 129.82, 143.22). Charac-
teristically, two signals appeared in the 13C NMR spec-
tra of IV–VI in the region corresponding to sp2-hy-
bridized carbon atoms. The upfield signal (δC 111–
120 ppm) was assigned to carbon atoms in the benzene
ring in the ortho position with respect to the oxygen
atom, and the downfield signal (δC 167–169 ppm) cor-
responds to the newly formed carbonyl group. The 13C
NMR spectra recorded without decoupling from pro-
ular ring closure occurs as a result of electrophilic
attack by the carbon atom of the thiocyanato group on
the hydroxy oxygen atom and proton transfer to the
nitrogen atom. Intermediate 5-amino-1,3-benzoxathiol-
2-imine B undergoes hydrolysis with formation of
final 5-amino-1,3-benzoxathiol-2-one IV–VI and lib-
eration of ammonia. In fact, addition of alkali to the
filtrate obtained after separation of the product and
subsequent heating resulted in evolution of an equi-
molar amount of ammonia. The latter was separated by
steam distillation into a receiver charged with distilled
water, and the distillate was titrated with 0.1 N hydro-
chloric acid (the amount of liberated ammonia was
determined only in experiments with potassium thio-
cyanate).
The crystalline and molecular structure of 4,7-di-
methyl-5-(p-tolylsulfonylamino)-1,3-benzoxathiol-2-
one (IVc) was determined by X-ray analysis (see
figure). Molecule IVc is composed of two planar frag-
ments. The first of these includes the p-tolyl substit-
uent and S1, and the second consists of the benzoxa-
thiol ring system and O4 and N1 atoms attached
thereto. The two fragments are almost orthogonal to
each other: the corresponding dihedral angle is 106.0°.
Such orientation makes conjugation between the ben-
zene and benzoxathiol fragments impossible, and the
C8–N1, N1–S1, and S1–C5 bonds [1.471(3), 1.673(2),
and 1.804(3) Å, respectively] are appreciably longer
than analogous standard bonds (1.390, 1.633, and
1.758 Å, respectively) [6]. Molecules IVc in crystal
1
tons, as well as H–13C heteronuclear correlation spec-
tra (HETCOR and LR HETCOR), were also consistent
with the assumed structure of compounds IV–VI.
Thus the NMR data for the initial compounds and
addition products showed that thiocyanate ion reacts
with quinone imines I–III as sulfur-centered nucleo-
phile and that the addition is followed by intramolec-
ular cyclization to N-substituted 5-amino-1,3-benzoxa-
thiol-2-ones IV–VI. A plausible mechanism of the
process is illustrated by Scheme 5. Presumably, in the
initial step 1,4-addition of thiocyanate ion gives N-sub-
stituted 4-amino-2-thiocyanatophenol A. Intramolec-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 3 2009

THIOCYANATION OF N-ARYLSULFONYL-, N-AROYL-, ...
411
Scheme 5.
O
O
SCN–
O
O
S
H2O
–NH3
H
N
NH
O
S
RNH
S
RNH
RNH
NR
I–III
A
B
IV–VI
form centrosymmetric dimers via weak intermolecular
hydrogen bonds N1–H1A···O2′ (1.5 – x, 0.5 – y, –z;
N···O 2.41 Å, ∠NHO 145°). In addition, short inter-
molecular contact S2···S2′ (2 – x, – y, 1 – x; 3.28 Å,
sum of the corresponding van der Waals radii 3.68 Å
[7]) was detected in crystal.
of thiocyanate–isothiocyanate isomerization which is
determined in turn by the substrate structure and reac-
tion conditions. The isomerization is strongly favored
by increased electrophilicity of the substrate [4].
Thus our results, in combination with the data of
[4], demonstrated that thiocyanate ion acts as sulfur-
centered nucleophile toward all the examined quinone
imines. The reaction with N-aryl-1,4-benzoquinone
imines may be accompanied by isomerization of initi-
ally formed thiocyanate into the corresponding isothio-
cyanate. The rate of isomerization of thiocyanates
derived from N-substituted 1,4-benzoquinone imines
I–III is considerably lower than the rate of their cy-
clization into benzoxathiole derivatives IV–VI.
In all the examined reactions, thiocyanation of
N-substituted 1,4-benzoquinone imines Ia–Ij, IIa–IIk,
and IIIa–IIIm followed a pattern different from that
reported in [1] for thiocyanation of N-(4-methyl-
phenyl)-1,4-benzoquinone imine. The substituent on
the nitrogen atom in N-aryl-1,4-benzoquinone imines
is a weak electron acceptor, and the redox potentials
of such quinone imines [8] are lower than those of
N-arylsulfonyl-, N-aroyl-, and N-(N-arylsulfonylbenz-
imidoyl)-1,4-benzoquinone imines [9]. Moreover,
N-aryl-1,4-benzoquinone imines are the strongest elec-
trophiles among the examined quinone imines. In most
cases, the structure of thiocyanation products (thiocya-
nato or isothiocyanato derivatives) depends on the rate
EXPERIMENTAL
1
The H and 13C NMR spectra were recorded from
solutions in DMSO-d6 or acetone-d6 (compound IVc)
on a Varian VXR-300 spectrometer (300 MHz); the
C15
O1
C4
C3
C10
C11
C9
C2
C1
O3
C5
S1
C8
O4
C7
N1
C6
O2
C12
C16
C13
S2
C14
Structure of the molecule of N-(4,7-dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-4-methylbenzenesulfonamide (IVc) according to the
X-ray diffraction data.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 3 2009

AVDEENKO et al.
412
chemical shifts were determined relative to tetrameth-
ylsilane. The IR spectra were measured in KBr on
a UR-20 instrument. Analytical thin-layer chromatog-
raphy was performed on Silufol UV-254 plates;
samples were applied from solutions in chloroform,
plates were eluted with benzene–hexane (10:1), and
spots were visualized under UV light.
4-Chloro-N-(2,6-dimethyl-4-oxocyclohexa-2,5-
dien-1-ylidene)benzamide (IIf). Yield 44%, mp 88–
89°C. Found, %: N 5.15, 5.38. C15H12ClNO2. Calculat-
ed, %: N 5.12.
4-Chloro-N-(2,3-dimethyl-4-oxocyclohexa-2,5-
dien-1-ylidene)benzamide (IIh). Yield 51%, mp 130–
131°C. Found, %: N 5.18, 4.96. C15H12ClNO2. Calcu-
lated, %: N 5.12.
X-Ray analysis of a single crystal of compound IVc
was performed at 293 K on an Xcalibur-3 diffractom-
eter (MoKα irradiation, CCD detector, graphite mono-
chromator, ω-scanning, 2θmax = 50°). Monoclinic crys-
tals, C16H15NO4S2, with the following unit cell param-
eters (293 K): a = 19.527(4), b = 18.949(4), c =
9.625(4) Å; β = 90.71(4)°; V = 3560.9(19) Å3; Mr =
349.41; Z = 8; space group C2/c; dcalc = 1.304 g/cm3;
µ(MoKα) = 0.316 mm–1; F(000) = 1456. Total of
16748 reflections were measured, 3127 of which were
independent (Rint = 0.041). The structure was solved by
the direct method using SHELXTL software package
[10]. The positions of hydrogen atoms were deter-
mined by dif-ference synthesis of electron density and
were refined according to the riding model (Uiso = nUeq
for non-hydrogen atom to which the given hydrogen
atom is attached; n = 1.5 for methyl group, n = 1.2 for
other hydrogen atoms). The structure was refined with
respect to F2 by full-matrix least-squares procedure in
anisotropic approximation for non-hydrogen atoms to
wR2 = 0.108 (16384 reflections) and R1 = 0.040 [1978
reflections with F > 4σ(F), S = 0.968]. The complete
set of crystallographic data, including coordinates of
atoms, was deposited to the Cambridge Crystallo-
graphic Data Centre (entry no. CCDC 681168).
N-(3,5-Dimethyl-4-oxocyclohexa-2,5-dien-1-
ylidene)-4-methoxybenzamide (IIj). Yield 31%,
mp 97.5–99°C. Found, %: N 5.29, 5.35. C16H15NO3.
Calculated, %: N 5.20.
4-Chloro-N-(3,5-dimethyl-4-oxocyclohexa-2,5-
dien-1-ylidene)benzamide (IIk). Yield 56%, mp 119–
121°C. Found, %: N 5.05, 4.91. C15H12ClNO2. Calcu-
lated, %: N 5.12.
N-(Cyclohexa-2,5-dien-1-ylidene)-N′-(4-methoxy-
phenylsulfonyl)benzimidamide (IIIa). Yield 67%,
mp 116–117°C. Found, %: N 7.40, 7.17; S 8.19, 8.30.
C20H16N2O4S. Calculated, %: N 7.36; S 8.43.
N-(3-Methylcyclohexa-2,5-dien-1-ylidene)-N′-(4-
methylphenylsulfonyl)benzimidamide (IIIb). Yield
47%, mp 104–105°C. Found, %: N 7.21, 7.29; S 8.66,
8.38. C21H18N2O3S. Calculated, %: N 7.40; S 8.44.
N-(2,5-Dimethylcyclohexa-2,5-dien-1-ylidene)-
N′-(phenylsulfonyl)benzimidamide (IIIc). Yield
80%, mp 120–121°C. Found, %: N 7.24, 7.57; S 8.19,
8.54. C21H18N2O3S. Calculated, %: N 7.40; S 8.47.
N-(2,3-Dimethylcyclohexa-2,5-dien-1-ylidene)-
N′-(4-methylphenylsulfonyl)benzimidamide (IIIi).
Yield 86%, mp 146–147°C. Found, %: N 6.95, 7.23;
S 8.47, 8.20. C22H20N2O3S. Calculated, %: N 7.14;
S 8.17.
Quinone imines Ia–Id and Ig–Ij were synthesized
as described in [11] by oxidation of the corresponding
aminophenols with sodium dichromate in acetic acid.
Quinone imines Ie, If, IIa–IIk, and IIIa–IIIm were
synthesized according to the procedure reported in [12]
by oxidation of the corresponding aminophenols with
lead tetraacetate in acetic acid. The properties of com-
pounds Ia [11], Ib [13], Ic [14], Id, IIb, IIc, IIId–IIIf
[15], Ie [16], Ig, Ih [17], Ii, Ij [18], IIa [19], IId, IIi
[20], IIg [21], IIIg, IIIh, IIIl, and IIIm [22] were
reported previously.
N-(2,3-Dimethylcyclohexa-2,5-dien-1-ylidene)-
N′-(4-methoxyphenylsulfonyl)benzimidamide (IIIj).
Yield 85%, mp 150.5–152°C. Found, %: N 7.00, 7.08;
S 7.59, 7.77. C22H20N2O4S. Calculated, %: N 6.86;
S 7.85.
N′-(4-Chlorophenylsulfonyl)-N-(2,3-dimethylcy-
clohexa-2,5-dien-1-ylidene)benzimidamide (IIIk).
Yield 79%, mp 160–161°C. Found, %: N 6.85, 6.87;
S 7.90, 8.12. C21H17ClN2O3S. Calculated, %: N 6.78;
S 7.77.
4-Chloro-N-(2,6-dimethyl-4-oxocyclohexa-2,5-
dien-1-ylidene)benzenesulfonamide (If). Yield 64%,
mp 105–106°C. Found, %: N 4.28, 4.49; S 10.01,
10.54. C14H12ClNO3S. Calculated, %: N 4.52; S 10.35.
Reaction of quinone imines I–III with potassium
or ammonium thiocyanate (general procedure). Po-
tassium or ammonium thiocyanate, 4 mmol, was added
to a solution of 2 mmol of quinone imine I–III in
15 ml of glacial acetic acid, the mixture was stirred,
N-(2,6-Dimethyl-4-oxocyclohexa-2,5-dien-1-
ylidene)-4-methoxybenzamide (IIe). Yield 40%,
mp 106–107°C. Found, %: N 5.17, 5.36. C16H15NO3.
Calculated, %: N 5.20.
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THIOCYANATION OF N-ARYLSULFONYL-, N-AROYL-, ...
413
left to stand for 12 h, and diluted with water until com-
plete precipitation of the product. The precipitate was
filtered off, washed with water, and recrystallized from
acetic acid.
%: N 3.89, 3.97; S 18.05, 18.64. C16H15NO4S2. Calcu-
lated, %: N 4.01; S 18.35.
4-Chloro-N-(4,6-dimethyl-2-oxo-1,3-benzoxa-
thiol-5-yl)benzenesulfonamide (IVf). Yield 80%,
mp 144–146°C. 1H NMR spectrum, δ, ppm: 1.97 s and
2.03 s (3H each, 4-CH3, 6-CH3), 7.23 (1H, 7-H), 7.68 s
(4H, 4-ClC6H4), 9.71 br.s (1H, NH). Found, %: N 3.78,
4.15; S 17.35, 17.69. C15H12ClNO4S2. Calculated, %:
N 3.79; S 17.34.
4-Methyl-N-(2-oxo-1,3-benzoxathiol-5-yl)ben-
zenesulfonamide (IVa). Yield 52%, mp 177–178°C.
1H NMR spectrum, δ, ppm: 2.34 s (3H, CH3), 7.46 d
(1H, 7-H, J = 7.8 Hz), 7.35–7.65 d.d (4H, C6H4CH3,
J = 7.8 Hz), 7.53–7.56 d.d (1H, 6-H, J = 7.8, 1.5 Hz),
7.55 d (1H, 4-H, J = 1.5 Hz), 10.39 br.s (1H, NH).
Found, %: N 4.26, 4.39; S 19.76, 20.04. C14H11NO4S2.
Calculated, %: N 4.36; S 19.95.
N-(6,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
benzenesulfonamide (IVg). Yield 66%, mp 201.5–
1
203°C. H NMR spectrum, δ, ppm: 1.88 s and 2.17 s
(6H, 6-CH3, 7-CH3), 7.24 s (1H, 4-H), 7.52–7.66 m
(5H, Ph), 9.78 s (1H, NH). Found, %: N 4.20, 4.06;
S 19.00, 19.05. C15H13NO4S2. Calculated, %: N 4.18;
S 19.12.
N-(7-Methyl-2-oxo-1,3-benzoxathiol-5-yl)ben-
zenesulfonamide (IVb). Yield 66%, mp 184–185°C.
1H NMR spectrum, δ, ppm: 2.23 s (3H, CH3), 6.92 d
(1H, 6-H, J = 1.5 Hz), 7.36 d (1H, 4-H, J = 1.8 Hz),
7.54–7.80 m (5H, Ph), 10.44 br.s (1H, NH). Found, %:
N 4.14, 4.26; S 19.70, 20.05. C14H11NO4S2. Calculated,
%: N 4.36; S 19.95.
N-(6,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methylbenzenesulfonamide (IVh). Yield 81%,
mp 171–173°C. 1H NMR spectrum, δ, ppm: 1.89 s and
2.18 s (6H, 6-CH3, 7-CH3), 2.37 s (3H, CH3C6H4),
7.24 s (1H, 4-H), 7.35–7.53 d.d (4H, C6H4, J =
8.1 Hz), 9.67 br.s (1H, NH). Found, %: N 3.77, 3.98;
S 18.20, 18.68. C16H15NO4S2. Calculated, %: N 4.01;
S 18.35.
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methylbenzenesulfonamide (IVc). Yield 82%,
1
mp 157.5–158°C. H NMR spectrum, δ, ppm: 2.04 s
and 2.25 s (3H each, 4-CH3, 7-CH3), 2.41 s (3H,
CH3C6H4), 6.93 s (1H, 6-H), 7.37–7.58 d.d (4H, C6H4,
J = 8.1 Hz), 8.57 br.s (1H, NH). Found, %: N 3.72,
3.85; S 18.13, 18.58. C16H15NO4S2. Calculated, %:
N 4.01; S 18.35.
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methylbenzamide (Va). Yield 63%, mp 199–201°C.
1H NMR spectrum, δ, ppm: 2.17 s and 2.34 s (6H,
4-CH3, 7-CH3), 2.39 s (3H, MeC6H4), 7.23 s (1H,
6-H), 7.34–7.89 d.d (4H, C6H4, J = 8.1 Hz), 10.03 s
(1H, NH). Found, %: N 4.40, 4.71; S 10.05, 11.04.
C17H15NO3S. Calculated, %: N 4.47; S 10.23.
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methoxybenzenesulfonamide (IVd). Yield 78%,
1
mp 153.5–155°C. H NMR spectrum, δ, ppm: 1.93 s
and 2.22 s (3H each, 4-CH3, 7-CH3), 3.82 s (3H,
MeO), 6.83 s (1H, 6-H), 7.08–7.56 d.d (4H, C6H4, J =
9.0 Hz), 9.62 br.s (1H, NH). 13C NMR spectrum, δC,
ppm: 14.89 and 16.16 (4-CH3, 7-CH3), 55.45 (MeO),
113.94 (C3′), 119.18 (C7), 122.55 (C3a), 126.52 (C5),
127.68 (C6), 128. 46 (C2′), 131.37 (C1′), 131.45 (C4′),
143.76 (C7a), 162.05 (C4′), 167.88 (C2). Found, %:
N 3.86, 3.98; S 17.02, 17.46. C16H15NO5S2. Calculat-
ed, %: N 3.83; S 17.55.
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-4-
methoxybenzamide (Vb). Yield 57%, mp 207–208°C.
1H NMR spectrum, δ, ppm: 9.92 s (1H, NH), 7.22 s
(1H, 6-H), 7.06–7.97 d.d (4H, C6H4, J = 8.4 Hz),
3.84 s (3H, MeO), 2.34 s and 2.17 s (3H each, 4-CH3,
7-CH3). 13C NMR spectrum, δC, ppm: 15.02 and 16.68
(4-CH3, 7-CH3), 55.33 (MeO), 113.49 (C3′), 119.19
(C7), 122.40 (C3a), 125.87 (C4), 126.10 (C1′), 127.34
(C6), 129.45 (C2′), 133.35 (C5), 143.62 (C7a), 161.84
(C4′), 164.92 (C=O), 168.14 (C2). Found, %: N 4.01,
4.32; S 9.38, 9.99. C17H15NO4S. Calculated, %:
N 4.25; S 9.73.
N-(4,6-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methylbenzenesulfonamide (IVe). Yield 72%
,
mp 163–164°C. 1H NMR spectrum, δ, ppm: 1.93 s and
2.01 s (3H each, 4-CH3, 6-CH3), 2.40 s (3H, CH3-
C6H4), 7.22 s (1H, 7-H), 7.39–7.56 d.d (4H, C6H4, J =
8.1 Hz), 9.53 br.s (1H, NH). 13C NMR spectrum, δC,
ppm: 17.68 and 18.45 (3-CH3, 6-CH3), 21.00 (Me-
C6H4), 111.23 (C7), 120.48 (C3a), 126.44 (C2′), 129.65
(C3′), 130.51 (C5), 132.39 (C4), 138.09 (C6), 138.51
(C1′), 143.05 (C4′), 145.67 (C7a), 168.14 (C2). Found,
4-Chloro-N-(4,7-dimethyl-2-oxo-1,3-benzoxa-
thiol-5-yl)benzamide (Vc). Yield 69%, mp 227–
1
228°C. H NMR spectrum, δ, ppm: 10.17 s (1H, NH),
7.62–8.00 d.d (4H, C6H4, J = 8.4 Hz), 7.24 s (1H,
6-H), 2.34 s and 2.18 s (6H, 4-CH3, 7-CH3). Found, %:
N 4.23, 4.41; S 9.34, 9.95. C16H12ClNO3S. Calculated,
%: N 4.20; S 9.61.
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AVDEENKO et al.
414
N-(4,6-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N-(7-Methyl-2-oxo-1,3-benzoxathiol-5-yl)-N′-(4-
methylphenylsulfonyl)benzimidamide (VIb). Yield
49%, mp 147–148°C. H NMR spectrum, δ, ppm:
2.22 s (3H, 7-CH3), 2.37 s (3H, CH3C6H4), 7.31–
7.52 d.d (4H, C6H4, J = 7.5 Hz), 7.37 br.s (1H, 6-H),
7.55–7.64 m (5H, Ph), 7.66 br.s (1H, 4-H), 10.66 s
(1H, NH). Found, %: N 6.47, 6.49; S 14.46, 14.50.
C22H18N2O4S2. Calculated, %: N 6.39; S 14.62.
4-methylbenzamide (Vd). Yield 62%, mp 201–203°C.
1H NMR spectrum, δ, ppm: 2.18 s and 2.24 s (6H,
4-CH3, 6-CH3), 2.39 s (3H, MeC6H4), 7.35 s (1H,
7-H), 7.35–7.91 d.d (4H, C6H4, J = 8.1 Hz), 9.85 s
(1H, NH). Found, %: N 4.48, 4.69; S 10.25, 10.42.
C17H15NO3S. Calculated, %: N 4.47; S 10.23.
1
N-(4,6-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methoxybenzamide (Ve). Yield 64%, mp 188–
189.5°C. 1H NMR spectrum, δ, ppm: 2.18 s and 2.24 s
(6H, 4-CH3, 6-CH3), 3.84 s (3H, MeO), 7.07–7.99 d.d
(4H, C6H4, J = 9.0 Hz), 7.34 s (1H, 7-H), 9.77 s
(1H, NH). Found, %: N 4.07, 4.39; S 9.54, 9.87.
C17H15NO4S. Calculated, %: N 4.25; S 9.73.
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(phenylsulfonyl)benzimidamide (VIc). Yield
1
60%, mp 207–208.5°C. H NMR spectrum, δ, ppm:
2.12 s and 2.28 s (3H each, 4-CH3, 7-CH3), 7.19 br.s
(1H, 6-H), 7.39–7.58 m (10H, Ph), 10.43 br.s (1H,
NH). Found, %: N 6.38, 6.55; S 14.07, 14.58.
C22H18N2O4S2. Calculated, %: N 6.39; S 14.62.
4-Chloro-N-(4,6-dimethyl-2-oxo-1,3-benzoxa-
thiol-5-yl)benzamide (Vf). Yield 76%, mp 194–
N-(4,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(4-methylphenylsulfonyl)benzimidamide (VId).
1
195°C. H NMR spectrum, δ, ppm: 10.02 s (1H, NH),
1
7.63–8.03 d.d (4H, C6H4, J = 8.4 Hz), 7.36 s (1H,
7-H), 2.24 s and 2.19 s (6H, 4-CH3, 6-CH3). Found, %:
N 4.19, 4.57; S 9.59, 9.68. C16H12ClNO3S. Calculated,
%: N 4.20; S 9.61.
Yield 63%, mp 204–205°C. H NMR spectrum, δ,
ppm: 2.13 s and 2.28 s (3H each, 4-CH3, 7-CH3),
2.32 s (3H, CH3C6H4), 7.18–7.38 d.d (4H, C6H4, J =
7.2 Hz), 7.22 br.s (1H, 6-H), 7.46–7.57 m (5H, Ph),
10.35 s (1H, NH). Found, %: N 6.00, 6.23; S 14.12,
14.83. C23H20N2O4S2. Calculated, %: N 6.19; S 14.17.
N-(6,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
4-methylbenzamide (Vg). Yield 53%, mp 193–194°C.
1H NMR spectrum, δ, ppm: 2.16 s and 2.31 s (6H,
6-CH3, 7-CH3), 2.39 s (3H, MeC6H4), 7.34–7.90 d.d
(4H, C6H4, J = 7.8 Hz), 7.55 s (1H, 4-H), 10.02 s (1H,
NH). 13C NMR spectrum, δC, ppm: 13.15 and 14.36
(6-CH3, 7-CH3), 21.03 (MeC6H4), 118.66 (C7), 119.34
(C4), 121.00 (C3a), 127.72 (C2′), 128.96 (C3′), 131.35
(C5), 133.50 (C6), 133.55 (C1′), 141.69 (C7a), 144.76
(C4′), 165.56 (C=O), 169.24 (C2). Found, %: N 4.25,
4.53; S 10.07, 10.63. C17H15NO3S. Calculated, %:
N 4.47; S 10.23.
N-(7-Isopropyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(4-methylphenylsulfonyl)benzimidamide (VIe).
1
Yield 68%, mp 164–166°C. H NMR spectrum, δ,
ppm: 1.15 d (6H, Me2CH, J = 6.6 Hz), 2.15 s (3H,
4-CH3), 2.32 s (3H, CH3C6H4), 3.04–3.17 m (1H,
Me2CH), 7.22–7.49 d.d (4H, C6H4, J = 7.8 Hz),
7.23 br.s (1H, 6-H), 7.42–7.64 m (5H, Ph), 10.31 s
(1H, NH). Found, %: N 5.67, 5.92; S 12.88, 13.37.
C25H24N2O4S2. Calculated, %: N 5.83; S 13.34.
N-(4-Isopropyl-7-methyl-2-oxo-1,3-benzoxathiol-
5-yl)-N′-(4-methylphenylsulfonyl)benzimidamide
4-Chloro-N-(6,7-dimethyl-2-oxo-1,3-benzoxa-
thiol-5-yl)benzamide (Vh). Yield 77%, mp 210–
1
(VIf). Yield 56%, mp 188–190°C. H NMR spectrum,
1
211°C. H NMR spectrum, δ, ppm: 2.16 s and 2.32 s
δ, ppm: 1.18 d (6H, Me2CH, J = 6.9 Hz), 2.31 s (6H,
CH3C6H4, 7-CH3), 3.17–3.31 m (1H, Me2CH), 7.18–
7.32 d.d (4H, C6H4, J = 7.8 Hz), 7.20 br.s (1H, 6-H),
7.45–7.58 m (5H, Ph), 10.38 br.s (1H, NH). Found, %:
N 5.38, 5.43; S 13.11, 13.58. C25H24N2O4S2. Calculat-
ed, %: N 5.83; S 13.34.
(6H, 6-CH3, 7-CH3), 7.55 s (1H, 4-H), 7.62–8.01 d.d
(4H, C6H4, J = 8.4 Hz), 10.16 s (1H, NH). Found, %:
N 4.05, 4.22; S 9.62, 9.98. C16H12ClNO3S. Calculated,
%: N 4.20; S 9.61.
N′-(4-Methoxyphenylsulfonyl)-N-(2-oxo-1,3-
benzoxathiol-5-yl)benzimidamide (VIa). Yield 74%,
N-(4,6-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(4-methylphenylsulfonyl)benzimidamide (VIg).
1
mp 178–180°C. H NMR spectrum, δ, ppm: 3.82 s
1
(3H, MeO), 6.99–7.46 d.d (4H, C6H4, J = 8.7 Hz),
7.40–7.71 m (5H, Ph), 7.58–7.61 d.d (1H, 6-H, J = 8.4,
1.5 Hz), 7.64 d (1H, 7-H, J = 8.4 Hz), 7.94 d (1H, 4-H,
J = 1.5 Hz), 10.67 br.s (1H, NH). Found, %: N 6.38,
6.43; S 14.28, 14.57. C21H16N2O5S2. Calculated, %:
N 6.36; S 14.56.
Yield 73%, mp 223–224°C. H NMR spectrum, δ,
ppm: 2.19 s and 2.26 s (3H each, 4-CH3, 6-CH3),
2.30 s (CH3C6H4), 7.16–7.24 d.d (4H, C6H4, J =
8.1 Hz), 7.37 br.s (1H, 7-H), 7.45–7.59 m (5H, Ph),
10.25 br.s (1H, NH). Found, %: N 6.21, 6.44; S 14.20,
14.67. C23H20N2O4S2. Calculated, %: N 6.19; S 14.17.
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THIOCYANATION OF N-ARYLSULFONYL-, N-AROYL-, ...
415
9.74 s (1H, OH). Found, %: N 5.51, 5.70. C16H17NO2.
Calculated, %: N 5.49.
N′-(4-Chlorophenylsulfonyl)-N-(4,6-dimethyl-
2-oxo-1,3-benzoxathiol-5-yl)benzimidamide (VIh).
1
Yield 78%, mp 228–230°C. H NMR spectrum, δ,
N-(4-Hydroxy-3,5-dimethylphenyl)-4-methoxy-
benzamide (VIIIj). Yield 72%, mp 194–196°C.
1H NMR spectrum, δ, ppm: 2.16 s (6H, 3-CH3, 5-CH3),
3.83 s (3H, MeO), 7.03–7.92 d.d (4H, C6H4, J =
9.0 Hz), 7.28 s (2H, 2-H, 6-H), 8.00 br.s (1H, NH),
9.73 s (1H, OH). Found, %: N 5.10, 5.28. C16H17NO3.
Calculated, %: N 5.16.
ppm: 2.19 s and 2.26 s (3H, 4-CH3, 6-CH3), 7.35–
7.43 d.d (4H, C6H4, J = 8.7 Hz), 7.37 br.s (1H, 7-H),
7.46–7.60 m (5H, Ph), 10.39 s (1H, NH). Found, %:
N 5.91, 6.32; S 13.51, 13.92. C22H17ClN2O4S2. Calcu-
lated, %: N 5.92; S 13.56.
N-(6,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(4-methylphenylsulfonyl)benzimidamide (VIi).
4-Chloro-N-(4-hydroxy-3,5-dimethylphenyl)-
benzamide (VIIIk). Yield 69%, mp 230–231°C.
1H NMR spectrum, δ, ppm: 2.16 s (6H, 3-CH3, 5-CH3),
7.29 s (3H, 2-H, 6-H), 7.58–7.95 d.d (4H, C6H4, J =
8.7 Hz), 8.02 br.s (1H, NH), 9.56 s (1H, OH). Found,
%: N 4.98, 5.16. C15H14ClNO2. Calculated, %: N 5.08.
1
Yield 82%, mp 201–202°C. H NMR spectrum, δ,
ppm: 2.10 s and 2.26 s (3H each, 6-CH3, 7-CH3),
2.32 s (3H, CH3C6H4), 7.20–7.36 d.d (4H, C6H4, J =
7.8 Hz), 7.44–7.58 m (5H, Ph), 7.47 br.s (1H, 4-H),
10.38 s (1H, NH). Found, %: N 6.07, 6.38; S 14.00,
14.73. C23H20N2O4S2. Calculated, %: N 6.19; S 14.17.
N-(4-Hydroxy-3,5-dimethylphenyl)-N′-(4-methyl-
phenylsulfonyl)benzimidamide (IXl). Yield 85%,
N-(6,7-Dimethyl-2-oxo-1,3-benzoxathiol-5-yl)-
N′-(4-methoxyphenylsulfonyl)benzimidamide (VIj).
1
mp 190–191°C. H NMR spectrum, δ, ppm: 2.05 s
1
(6H, 3-CH3, 5-CH3), 2.36 s (3H, CH3C6H4), 7.10 s
(2H, 2-H, 6-H), 7.31–7.58 d.d (4H, C6H4, J = 7.8 Hz),
7.45–7.55 m (5H, Ph), 8.30 s (1H, NH), 10.27 s
(1H, OH). Found, %: N 7.12, 7.31; S 8.02, 8.23.
C22H22N2O3S. Calculated, %: N 7.10; S 8.13.
Yield 73%, mp 186–187°C. H NMR spectrum, δ,
ppm: 2.10 s and 2.26 s (3H each, 6-CH3, 7-CH3),
3.78 s (3H, MeO), 6.91–7.38 d.d (4H, C6H4, J =
8.7 Hz), 7.41–7.59 m (5H, Ph), 7.42 br.s (1H, 4-H),
10.35 br.s (1H, NH). Found, %: N 6.01, 6.18; S 13.22,
13.65. C23H20N2O5S2. Calculated, %: N 5.98; S 13.69.
N′-(4-Chlorophenylsulfonyl)-N-(4-hydroxy-3,5-
dimethylphenyl)benzimidamide (IXm). Yield 80%,
N′-(4-Chlorophenylsulfonyl)-N-(6,7-dimethyl-
1
mp 185–186°C. H NMR spectrum, δ, ppm: 2.05 s
2-oxo-1,3-benzoxathiol-5-yl)benzimidamide (VIk).
(6H, 3-CH3, 5-CH3), 7.07 s (2H, 2-H, 6-H), 7.57–
7.93 d.d (4H, C6H4, J = 8.4 Hz), 7.49–7.62 m (5H, Ph),
8.31 s (1H, NH), 10.40 s (1H, OH). Found, %: N 6.59,
6.80; S 7.65, 7.83. C21H19ClN2O3S. Calculated, %:
N 6.75; S 7.73.
1
Yield 71%, mp 244–245°C. H NMR spectrum, δ,
ppm: 2.11 s and 2.27 s (6H, 6-CH3, 7-CH3), 7.38 br.s
(1H, 4-H), 7.46 s (4H, C6H4), 7.48–7.59 m (5H, Ph),
10.55 s (1H, NH). Found, %: N 5.77, 6.21; S 13.02,
13.53. C22H17ClN2O4S2. Calculated, %: N 5.92;
S 13.56.
REFERENCES
N-(4-Hydroxy-3,5-dimethylphenyl)-4-methyl-
benzenesulfonamide (VIIi). H NMR spectrum, δ,
ppm: 2.03 s (6H, 3-CH3, 5-CH3), 2.33 s (3H, CH3-
C6H4), 6.61 s (2H, 2-H, 6-H), 7.31–7.56 d.d (4H, C6H4,
J = 8.4 Hz), 8.08 br.s (1H, NH), 9.60 s (1H, OH).
1
1. Burmistrov, K.S., Toropin, N.V., Burmistrov, S.A., and
Nichvoloda, V.M., Zh. Org. Khim., 1992, vol. 28, p. 1900.
2. Rajappa, S. and Shenoy, S.J., Tetrahedron, 1986, vol. 42,
p. 5739.
3. Becker, H., Einführung in die Elektronentheorie orga-
nisch–chemischer Reaktionen, Berlin: Wissenschaften,
1974, 3rd ed. Translated under the title Vvedenie v
elektronnuyu teoriyu organicheskikh reaktsii, Moscow:
Mir, 1977, p. 118; Kostikov, R.R. and Bespalov, V.Ya.,
Osnovy teoreticheskoi organicheskoi khimii (Basic
Principles of Theoretical Organic Chemistry), Leningrad:
Leningr. Gos. Univ., 1982, p. 180.
4. Loos, R., Kobayashi, S., and Mayr, H., J. Am. Chem.
Soc., 2003, vol. 125, p. 14126.
5. Avdeenko, A.P., Evgrafova, N.I., and Yusina, A.L., Vopr.
Khim. Khim. Tekhnol., 2000, no. 3, p. 7.
4-Chloro-N-(4-hydroxy-3,5-dimethylphenyl)-
benzenesulfonamide (VIIj). Yield 79%, mp 148–
149°C. 1H NMR spectrum, δ, ppm: 2.04 s (6H, 3-CH3,
5-CH3), 6.61 s (2H, 2-H, 6-H), 7.61–7.67 d.d (4H,
C6H4, J = 8.7 Hz), 8.14 br.s (1H, NH), 9.75 s (1H,
OH). Found, %: N 4.53, 4.69; S 10.11, 10.35.
C14H14ClNO3S. Calculated, %: N 4.49; S 10.28.
N-(4-Hydroxy-3,5-dimethylphenyl)-4-methyl-
benzamide (VIIIi). Yield 73%, mp 217–218°C.
1H NMR spectrum, δ, ppm: 2.16 s (6H, 3-CH3, 5-CH3),
2.37 s (3H, CH3C6H4), 7.29 s (2H, 2-H, 6-H), 7.29–
7.84 d.d (4H, C6H4, J = 8.1 Hz), 8.03 br.s (1H, NH),
6. Burgi, H.-B. and Dunitz, J.D., Structure Correlation,
Weinheim: VCH, 1994, vol. 2, p. 741.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 3 2009

AVDEENKO et al.
416
7. Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989,
15. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A.,
Ludchenko, O.N., and Marchenko, I.L., Russ. J. Org.
Chem., 2009, vol. 45, p. 383.
vol. 58, p. 713.
8. Burmistrov, K.S. and Burmistrov, S.I., Ukr. Khim. Zh.,
16. Avdeenko, A.P., Menafova, Yu.V., and Zhukova, S.A.,
1978, vol. 44, p. 832.
Russ. J. Org. Chem., 1998, vol. 34, p. 210.
17. Avdeenko, A.P. and Konovalova, S.A., Vopr. Khim.
Khim. Tekhnol., 2002, no. 4, p. 29.
9. Burmistrov, K.S., Toropin, N.V., Vakulenko, A.V.,
Yurchenko, A.G., and Markov, V.I., Vopr. Khim. Khim.
Tekhnol., 2000, no. 2, p. 30.
10. Sheldrick, G.M., SHELXTL PLUS. PC Version. A Sys-
tem of Computer Programs for the Determination of
Crystal Structure from X-Ray Diffraction Data. Rev. 5.1,
1998.
11. Burmistrov, K.S. and Titov, E.A., Zh. Obshch. Khim.,
1952, vol. 22, p. 999.
12. Avdeenko, A.P., Burmistrov, K.S., Dubina, V.L., and
Skripets, V.I., Ukr. Khim. Zh., 1980, vol. 46, p. 1081.
13. Avdeenko, A.P. and Konovalova, S.A., Vopr. Khim.
Khim. Tekhnol., 2002, no. 1, p. 20.
14. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org.
Chem., 2006, vol. 42, p. 669.
18. Avdeenko, A.P., Russ. J. Org. Chem., 2000, vol. 36,
p. 522.
19. Avdeenko, A.P., Konovalova, S.A., and Ludchen-
ko, O.N., Vopr. Khim. Khim. Tekhnol., 2006, no. 5, p. 60.
20. Avdeenko, A.P., Konovalova, S.A., and Ludchen-
ko, O.N., Vopr. Khim. Khim. Tekhnol., 2006, no. 6, p. 36.
21. Avdeenko, A.P., Konovalova, S.A., and Ludchen-
ko, O.N., Vopr. Khim. Khim. Tekhnol., 2006, no. 6, p. 48.
22. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A.,
Burmistrov, K.S., Nichvoloda, V.M., Shishkin, O.V.,
Zubatyuk, R.I., and Palamarchuk, G.V., Russ. J. Org.
Chem., 2009, vol. 45, p. 48.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 3 2009