Synthesis of substituted thiazol-2-yl-acetamides. Molecular and crystal structure of N-(4-methoxyphenyl)-2-oxo-2-(4-phenylthiazol-2-yl)acetamide

Article abstract of DOI:10.1134/S1070363215050060

Reaction of 3-amino-3-thioxopropanamides with α-bromoketones has afforded substituted thiazol-2-yl-acetamides. Structure of N-(4-methoxyphenyl)-2-oxo-2-(4-phenylthiazol-2-yl)acetamide has been studied by X-ray diffraction.

Full text of DOI:10.1134/S1070363215050060

ISSN 1070-3632, Russian Journal of General Chemistry, 2015, Vol. 85, No. 5, pp. 1043–1048. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © I.V. Dyachenko, V.D. Dyachenko, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 5, pp. 745–750.
Synthesis of Substituted Thiazol-2-yl-acetamides.
Molecular and Crystal Structure
of N-(4-Methoxyphenyl)-2-oxo-2-(4-phenylthiazol-2-yl)acetamide
I. V. Dyachenko and V. D. Dyachenko
Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011 Ukraine
e-mail: dyachvd@mail.ru
Received February 2, 2015
Abstract—Reaction of 3-amino-3-thioxopropanamides with α-bromoketones has afforded substituted thiazol-
2
-yl-acetamides. Structure of N-(4-methoxyphenyl)-2-oxo-2-(4-phenylthiazol-2-yl)acetamide has been studied
by X-ray diffraction.
Keywords: 3-amino-3-thioxopropanamide, α-bromoketones, thiazol-2-yl-acetamides, XRD
DOI: 10.1134/S1070363215050060
3
-Amino-3-thioxopropanamides are used in organic
leading to peroxide VI. Peroxide VI was further trans-
synthesis as CH-acids in preparation of functionally
substituted pyridines via the Michael reaction [1–4] as
well as C-nucleophiles in nucleophilic vinyl substitution
formed into N-(4-methoxyphenyl)-2-oxo-2-(4-phenyl-
thiazol-2-yl)acetamide VII via elimination of water
and hydrogen bromide.
[
[
5, 6] and condensation with carbonyl compounds
7, 8]. Alkylation of 3-amino-3-thioxopropanamides
Structures of compounds IIIa–IIIf and IV were
confirmed by the spectral data. In particular, the IR
spectra contained characteristic absorption bands of
results in S-methyl derivatives [9].
–1
Extending our earlier studies on transformation of
-amino-3-thioxopropanamides [10–13], herein we
carbonyl group stretching at 1658–1714 cm . A singlet
signal of the methylene protons at 3.91–4.41 ppm was
3
1
report on reactions of amides Ia and Ib with α-
bromoketones IIa–IIf at 20°C in DMF.
observed in H NMR spectra of compounds IIIa–IIIf.
Mass spectrum of IIIf contained a weak peak of
+
[
M + 2] confirming the presence of sulfur atoms in the
The reaction led to formation of the substituted
Hantzsch thiazoles IIIa–IIIf, promising precursors for
preparation of antimicrobial [14, 15] and antitumor
molecule [21]. The molecular ion peak with even mass
number pointed at an even number of nitrogen atoms
1
3
in the molecule of compound IV [22]. C NMR
spectrum of VII contained the signals of all the carbon
atoms of the suggested structure with the expected
chemical shifts.
[16, 17] drugs. Some of the Hantzsch thiazoles have
demonstrated substantial efficiency in treatment of
Alzheimer's disease [18] and as a fluorescent probe
[19] (Scheme 1).
Structure of compound VII was studied by single
crystal X-ray diffraction (Figs. 1–3, Tables 1 and 2).
Apparently, the discussed reaction proceeded via
formation of intermediate IV followed by intramo-
lecular cyclization into the substituted thiazolium
bromide V. The latter was hydrolyzed to yield thiazole
III. In the case of thioamide Ia and phenacyl bromide
IIa, the reaction did not stop at the stage of formation
of thiazole III. The presence of π-deficient thiazolium
cation near the methylene group in the molecule of
intermediate V promoted its oxidation [20] with air
oxygen upon exposition of the solution to light,
Independent part of the unit cell contained two
molecules of compound VII with similar geometry
parameters. Oxoacetamide fragment was located in the
plane of the thiazole ring (the angle between the
average planes was of 7.1° in the molecule A and of
6.6° in the molecule B). The methoxyphenyl moiety
was almost coplanar with the oxoacetamide fragment
5
2
6
7
[the С N C C torsion angles were of –23.4(3)° (А)
1
043

1
044
I.V. DYACHENKO, V.D. DYACHENKO
Scheme 1.
R2
Br
R2
O
O
S
O
S
O
S
HBr
IIa−IIf
O
O
+
1
1
1
R2
Br
R HN
NH2
−HBr
R HN
NH
R HN
N
−H O
2
−
H
Ia, Ib
IV
V
O , hν
2
−
HBr
O
S
S
H
O
O
S
Ph
Ph
+
N
HN
N
MeO
HN
MeO
1
R2
−
−
H O,
R HN
N
2
−
O
HBr
H
Br
HO
VI
VII
(a), Н (b); II, R = Ph (a), 4-МеОС
IIIа−IIIf
(d), 3-oxo-3H-benzo[f]-
1
2
I, R = 4-МеОС
chromen-2-yl (e), 4-NО
b); R = 4-МеОС
R = coumarin-3-yl (f).
6
Н
4
6
Н
4
(b), coumarin-3-yl (c), 4-МеС
(a); R = 4-МеОС
Н , R = 4-NО С Н (d); R = Н, R = 4-МеС Н (e); R = Н,
4 2 6 4 6 4
6
Н
4
1
2
1
2
2
С
6
Н
4
(f); III, R = R = 4-МеОС
6
Н
4
6
Н
4
, R = 3-oxo-3H-benzo[f]chromen-2-yl
1
2
1
2
1
2
1
(
6
Н
4
, R = coumarin-3-yl (c); R = 4-МеОС
6
2
7
7
2
Apparently, the S···O intermolecular interactions
could be described as σ-hole bonds, as evidenced by
and of –13.8(3)° (В)], and the С –Н ···О intramole-
cular hydrogen bond [H···O 2.30Å (A) and 2.28 Å (B),
C–H···O 117° (A) and 121° (B)] was formed. The
phenyl substituent of molecule B was located almost in
3
1
2
the proximity of the C –S ···O angle (147°–162°) to
80°. To confirm the assumption, we performed
1
1
2
12 17
quantum-chemical simulation of electrostatic potential
of the molecules VII dimer (Fig. 3). The region of the
positive electrostatic potential at continuation of the
the thiazole ring plane [the C C C C torsion angle of
.3(3)°] resulting in a shortened intermolecular contact
7
1
17
Н ···Н (2.27 Å with the sum of the van der Waals
radii being of 2.32 Å [23 ]). The similar shortened
contact was not formed in the molecule A due to a
small rotation of the phenyl substituent with respect to
3
1
C –S bond was oriented towards the area of the
2
negative electrostatic potential of the O atom of the
adjacent molecule. On top of that, the molecule
1
2
1
2 12 17
contained the S ···O intramolecular σ-hole bonding
2.68Å (А) and 2.72 Å (В)] between the region of
positive electrostatic potential at continuation of the
the thiazole ring [the C C C C torsion angle of 19.2(3)°].
[
The molecules were linked into the A···B dimers
via intermolecular hydrogen bonding N –H ···O
H···O 2.16 Å, N–H···O 161°) and N –H ···O
H···O 2.30 Å, N–H···O 164°) in the crystal (Fig. 2).
Those dimers were linked into chains along the c axis
2
A
2A
1B
1
1
С –S bond and the region of negative potential of the
lone-electron pair of the oxygen atom. Existence of
such intramolecular S···O bonds has been shown
earlier [24].
2
В
2В
1А
(
(
2
A
1B
of the lattice due to intermolecular contacts O ···S
2
В
1A
3
.16 Å and О ···S 3.08 Å between the molecules A
and B (the sum of the van der Waals radii being of
.11 Å) .
EXPERIMENTAL
3
IR spectra of KBr pellets were recorded with a UR-
1
13
2
0 spectrophotometer. H and C NMR spectra of
solutions in DMSO-d were recorded with a Varian-
6
Gemini spectrometer (400.13 and 100 MHz,
respectively) relative to TMS as internal reference.
Elemental analysis was performed using an
EuroVector EA–3000 microanalyzer. Chromato-mass
spectroscopy studies were performed using an Agilent
2
C
1
100/DAD/HSD/VLG 119562 and MX-1321 (70 eV)
Fig. 1. General view of the molecule of compound VII.
devices. Melting points were determined using a
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 5 2015

SYNTHESIS OF SUBSTITUTED THIAZOL-2-YL-ACETAMIDES
1045
Fig. 2. Crystal packing of the molecule of compound VII.
Kofler bench. The reaction progress was monitored by
TLC on Silufol UV-254 plates, eluting with acetone–
hexane mixture (3 : 5) and detecting with iodine
vapors or UV irradiation
3-Amino-N-(4-methoxyphenyl)-3-thioxopropan-
amide (Ia) was prepared as described in Ref. [8]. Lilac
plate crystals, sublimation point 138–139°C (mp 143–
1
144°C [8]). H NMR spectrum, δ, ppm: 3.64 s (2Н,
СН ), 3.72 s (3Н, Ме), 6.84 d (2Н, Нarom, J 8.0 Hz),
2
Single crystal X-ray diffraction. Crystals of com-
pound VII were monoclinic, C H N O S; the unit
7
.51 d (2Н, Нarom, J 8.0 Hz), 9.36 br.s (1Н, NН ), 9.64
2
1
8
14
2
3
br.s (1Н, NН ), 9.97 br.s (1Н, NН).
2
cell parameters at 298 K: a = 20.1357(11), b = 7.1124(6),
3
3
-Amino-3-thioxopropanamide (Ib) was prepared
c = 23.4523(14) Å, β = 112.893(7)°, V = 3094.1(4) Å ,
–
3
as described in Ref. [8]. Yellow crystals, mp 105–107°C
M = 338.37, Z = 2, space group P2 /с, d = 1.45 g cm ,
1
calc
1
–
1
(
mp 103–105°C [8]). H NMR spectrum, δ, ppm: 3.42
μ(MoK ) = 0.229 mm , F(000) = 1408. The unit cell
α
parameters and intensities of the 25420 reflections
(
9784 independent ones, Rint = 0.044) were measured
with an Xcalibur automatic four-circle diffractometer
MoK , graphitic monochromator, CCD-detector, ω-scan,
(
α
2
θmax = 64.02°).
The structure was solved via the direct method
using SHELX-97 software [25]. The hydrogen atoms
were geometrically positioned and refined using a
rider model with Uiso = nU (n = 1.5 for the methyl
eq
group and n = 1.2 for other of hydrogen atoms). The
2
structure was refined via F full-matrix least-squares
method using anisotropic approximation for non-
hydrogen atoms to wR 0.143 over 9784 reflections
2
Fig. 3. Simulated electrostatic potential map of molecules
VII dimer linked via σ-hole O···S bonds (experimental
geometry, B3LYP/TZVP, isosurface of electron density
value of 0.025 a. u.).
[R1 = 0.053 over 5512 reflections with F > 4σ(F), S =
1
1
.01]. The bond lengths and angles are listed in Tables
and 2, respectively.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 5 2015

1
046
I.V. DYACHENKO, V.D. DYACHENKO
Table 1. Bond lengths (Å) in the molecule of compound VII
Bond
A
B
Bond
A
B
1
1
4
5
S –C
1.6778(19)
1.7120(16)
1.2124(19)
1.2147(19)
1.3755(19)
1.417(2)
1.368(2)
1.316(2)
1.334(2)
1.416(2)
1.6788(19)
1.7162(16)
1.2074(19)
1.220(2)
1.370(2)
1.413(2)
1.358(2)
1.315(2)
1.334(2)
1.418(2)
1.370(2)
1.475(2)
1.468(2)
C –C
1.535(2)
1.384(2)
1.388(2)
1.386(2)
1.375(2)
1.384(2)
1.376(2)
1.383(2)
1.389(2)
1.383(2)
1.379(3)
1.374(3)
1.375(2)
1.534(2)
1.388(2)
1.388(2)
1.384(2)
1.377(3)
1.384(2)
1.375(2)
1.381(2)
1.391(3)
1.381(3)
1.368(3)
1.376(3)
1.377(3)
1
3
6
7
S –C
C –C
1
4
6
11
O –C
C –C
2
5
7
8
O –C
C –C
3
9
8
9
O –C
C –C
3
18
9
10
O –C
C –C
1
2
10
11
13
17
14
15
16
17
N –C
C –C
1
3
12
N –C
C –C
2
5
12
N –C
C –C
2
6
13
N –C
C –C
1
2
14
C –C
1.371(2)
1.474(2)
1.471(2)
C –C
2
12
15
C –C
C –C
3
4
16
C –C
C –C
Table 2. Bond angles (deg) in the molecule of compound VII
Angle
A
B
Angle
A
B
1
1
3
7
6
11
C S C
89.27(8)
89.23(9)
C C C
C C N
119.37(15)
118.26(15)
120.11(16)
120.28(16)
115.86(15)
124.45(16)
119.69(16)
120.34(16)
120.17(16)
120.75(16)
118.70(16)
120.55(16)
120.44(18)
120.27(19)
119.52(19)
120.45(19)
120.63(18)
119.21(16)
117.91(15)
120.14(17)
120.33(17)
115.20(16)
125.33(16)
119.47(16)
120.56(17)
120.19(16)
120.25(16)
118.32(17)
121.42(17)
120.58(19)
120.8(2)
9
3
18
2
11
6
2
C O C
116.91(15)
110.33(13)
126.04(14)
111.53(13)
113.95(15)
120.00(14)
126.04(16)
114.91(13)
120.64(14)
124.42(13)
122.63(15)
120.08(15)
117.29(14)
125.74(16)
120.17(15)
114.09(14)
122.37(15)
117.49(16)
110.80(14)
127.81(14)
111.41(14)
114.09(15)
119.60(15)
126.31(16)
114.46(13)
121.07(14)
124.47(13)
122.01(15)
119.92(15)
118.07(15)
125.84(16)
120.87(15)
113.29(15)
122.87(15)
3
1
6
7
8
C N C
C C C
5
2
6
9
8
7
C N C
C C C
2
1
1
3
9
10
C C S
O C C
1
2
1
8
9
3
N C C
C C O
1
2
12
8
9
10
N C C
C C C
1
2
12
11 10
9
6
2
C C C
C C C
1
3
1
10 11
N C S
C C C
1
3
4
13 12
N C C
C C C
4
3
1
13 12 17
C C S
C C C
1
4
3
5
17 12
2
O C C
C C C
1
4
12 13 14
O C C
C C C
3
4
5
15 14 13
C C C
C C C
2
5
2
16 15 14
O C N
C C C
119.23(19)
120.5(2)
2
5
4
4
2
15 16 17
O C C
C C C
2
5
16 17 12
N C C
C C C
120.62(19)
7
6
C C N
s (2Н, СН ), 6.96 br.s (1Н, СОNН ), 7.41 br.s (1Н,
water and incubated during 4 days. The resulting
precipitate was filtered off and sequentially washed
with water, ethanol, and hexane.
2
2
СОNН ), 9.29 br.s (1Н, СSNН ), 9.43 br.s (1Н, СSNН ).
2
2
2
Substituted thiazol-2-ylacetamides (IIIa–IIIe)
and N-(4-methoxyphenyl)-2-oxo-2-(4-phenylthiazol-
N-(4-Methoxyphenyl)-2-[4-(4-methoxyphenyl)-
thiazol-2-yl]acetamide (IIIa). Yield 2.9 g (82%),
yellow powder, mp 151–152°C (PrOH). IR spectrum,
2
-yl)acetamide (VII) (general procedure). 10 mmol
of the corresponding α-bromoketone III was added to
a stirred solution of 10 mmol of thioxopropanamide Ia
or Ib in 20 mL of DMF at 20°C. The mixture was
stirred for 2 h and then incubated during 48 h. The
reaction mixture was diluted with equal volume of
–
1
1
ν, cm : 3300 (NH), 1672 (CОNН). H NMR spec-
trum, δ, ppm: 3.74 s (3Н, МеО), 3.84 s (3Н, МеО),
4.08 s (2Н, СН ), 6.77 d (2Н, Н , J 8.5 Hz), 6.88 d
2
arom
5
(2Н, Нarom, J 8.4 Hz),7.45 s (1Н, С Н, thiazole), 7.51 d
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 5 2015

SYNTHESIS OF SUBSTITUTED THIAZOL-2-YL-ACETAMIDES
1047
(
1
(
2Н, Нarom, J 8.5 Hz), 7.79 d (2Н, Нarom, J 8.4 Hz),
0.01 br.s (1Н, NН). Mass spectrum, m/z (I ,%): 355
100) [M + 1] . Found, %: С 64.25; Н 5.01; N 7.84.
Нarom, J 7.7 Hz), 7.59 br.s (1Н, NН ), 7.82 d (2Н,
2
5
Нarom, J 7.7 Hz), 7.85 s (1Н, С Н, thiazole). Mass
rel
+
+
spectrum, m/z (I , %): 234 (4) [M + 2] , 233 (9)
rel
+
+
+
С Н N О S. Calculated, %: С 64.39; Н 5.12; N 7.90.
[M + 1] , 232 (59) [M] , 215 (2) [M – NH ] , 189
(100) [M – СН СО] , 148 (35), 134 (12), 115 (11), 91
6) [PhCH ] , 77 (5) [Ph] , 44 (9) [CS] . Found, %: С
1
9
18
2
3
3
+
М 354.425.
N-(4-Methoxyphenyl)-2-[4-(3-oxo-3H-benzo[f]-
chromen-2-yl)thiazol-2-yl]acetamide (IIIb). Yield
.7 g (62%), yellow powder, mp 216–217°C (DMF),
3
+
+
+
(
2
6
6
1.96; Н 5.02; N 11.94. С Н N ОS. Calculated, %: С
2.05; Н 5.21; N 12.06. М 232.303.
12
12
2
2
–
1
sublimation point 170°C. IR spectrum, ν, cm : 3314
(
δ, ppm: 3.76 s (3Н, Ме), 4.18 s (2Н, СН ), 7.82 d (2Н,
Нarom, J 8.6 Hz), 7.45–7.61 m (3Н, Нarom), 7.73 t (1Н,
2-[5-(2-Oxo-2H-chromen-3-yl)thiazol-2-yl]acet-
1
NH), 1711 (С=О), 1666 (CОNН). H NMR spectrum,
amide (IIIf). Yield 2.3 g (82%) colorless powder, mp
–
1
211–213°C (BuOH). IR spectrum, ν, cm : 3402, 3385,
2
1
3287 (NH ), 1714 (С=О), 1671 (CОNН). H NMR
2
Нarom, J 8.1 Hz), 7.96 d (2Н, Нarom, J 8.6 Hz), 8.07 d
spectrum, δ, ppm: 3.91 s (2Н, СН ), 7.05 br.s (1Н,
2
5
(
1Н, Нarom, J 8.3 Hz), 8.42 s (1Н, С Н, thiazole), 8.46
NН ), 7.21–7.42 m (2Н, Н , NН ), 7.44–7.65 m (2Н,
2
arom
2
1
5
d (1Н, Нarom, J 8.4 Hz), 9.49 s (1Н, С Н, chromen),
0.06 br.s (1Н, NН). Mass spectrum, m/z (I ,%): 443
Нarom), 7.78 d (1Н, Н , J 7.6 Hz), 8.28 s (1Н, С Н,
thiazole), 8.73 s (1Н, С Н, coumarin). Mass spectrum,
m/z (I ,%): 287 (100) [M + 1] . Found, %: С 58.64; Н
arom
4
1
rel
+
+
(
100) [M + 1] . Found, %: С 67.74; Н 3.98; N 6.28.
rel
С Н N О S. Calculated, %: С 67.86; Н 4.10; N 6.33.
3.43; N 9.66. С Н N О S. Calculated, %: С 58.73; Н
2
5
18
2
4
14 10
2
3
М 442.492.
N-(4-Methoxyphenyl)-2-[4-(2-oxo-2H-chromen-
-yl)thiazol-2-yl]acetamide (IIIc). Yield 3.0 g (76%)
colorless powder, mp 201–202°C (BuOH). IR
3.52; N 9.78. М 286.308.
N-(4-Methoxyphenyl)-2-oxo-2-(4-phenylthiazol-
2-yl)acetamide (VII). Yield 2.2 g (66%), yellow
needles, mp 198–200°C (BuOH). IR spectrum, ν, cm :
3
–
1
–
1
1
spectrum, ν, cm : 3296 (NH), 1702 (С=О), 1670
3322 (NH), 1658 (С=О). H NMR spectrum, δ, ppm:
1
(
4
(
CОNН). H NMR spectrum, δ, ppm: 3.72 s (3Н, Ме),
.21 s (2Н, СН ), 6.91 d (2Н, Н , J 8.7 Hz), 7.39 t
3.78 s (3Н, Ме), 6.87 d (2Н, Нarom, J 8.5 Hz), 7.35 t
(1Н, Нarom, J 7.0 Hz), 7.44 t (2Н, Нarom, J 7.5 Hz), 7.75
d (2Н, Нarom, J 8.5 Hz), 8.03 d (2Н, Нarom, J 7.0 Hz),
2
arom
7
5
1Н, С Н, coumarin, J 8.1 Hz), 7.47 d (1Н, С Н, coumarin,
1
3
J 8.1 Hz), 7.54 d (2Н, Н , J 8.7 Hz), 7.65 t (1Н,
10.81 br.s (1Н, NН). С NMR spectrum, δ , ppm:
arom
C
6
8
С Н, coumarin, J 8.1 Hz), 7.94 d (1Н, С Н, coumarin,
J 8.1 Hz), 8.36 s (1Н, С Н, thiazole), 8.77 s (1Н, С Н,
55.73, 114.57, 122.34, 124.98, 126.87, 129.42, 129.51,
130.97, 133.54, 156.79, 157.12, 159.38, 160.48, 178.84.
5
4
+
coumarin), 10.26 br.s (1Н, NН). Mass spectrum, m/z
Mass spectrum, m/z (I , %): 339 (100) [M + 1] .
rel
+
(
I ,%): 393 (100) [M + 1] . Found, %: С 64.18; Н
Found, %: С 63.78; Н 4.00; N 8.11. С Н N О S.
rel
18 14
2
3
3
4
.95; N 7.02. С Н N О S. Calculated, %: С 64.27; Н
.11; N 7.14. М 392.432.
Calculated, %: С 63.89; Н 4.17; N 8.28. М 338.384.
2
1
16
2
4
REFERENCES
N-(4-Methoxyphenyl)-2-[4-(4-nitrophenyl)thiazol-
-yl]acetamide (IIId). Yield 2.8 g (76%), yellow
2
1
2
. Krauze, A. and Duburs, G., Khim. Geterotsykl. Soed.,
999, no. 4, p. 506.
–
1
powder, mp 189–190°C (AcOH). IR spectrum, ν, cm :
3
4
J 8.6 Hz), 7.77 d (2Н, Нarom, J 8.6 Hz), 8.38 s (1Н,
С Н, thiazole), 8.44 d (2Н, Нarom, J 8.3 Hz), 8.53 d
1
1
315 (NH), 1662 (CОNН). H NMR spectrum, δ, ppm:
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.02 s (3Н, Ме), 4.41 s (2Н, СН ), 7.06 d (2Н, Нarom,
2
5
3. Rodinivskaya, L.A., Shestopalov, A.M., and Nesterov, V.N.,
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(
2Н, Нarom, J 8.3 Hz), 10.33 br.s (1Н, NН). Mass
+
4
5
. Krasnikov, D.A., Dyachenko, V.D., and Shishkin, O.V.,
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spectrum, m/z (I ,%): 370 (100) [M + 1] . Found, %:
С 58.45; Н 3.92; N 11.24. С Н N О S. Calculated,
%
rel
18
15
3
4
1
0.1134/S1070363210020234.
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: С 58.53; Н 4.09; N 11.36. М 369.397.
-[5-(p-Tolyl)thiazol-2-yl]acetamide (IIIe). Yield
.7 g (75%), colorless needles, mp 131°C (EtOH). IR
2
2
1
–
1
spectrum, ν, cm : 3390, 3300, 3280 (NH ), 1680
2
6. Dyachenko, V.D., Bityukova, O.S., and Dyachenko, A.D.,
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1
(
3
CОNН). H NMR spectrum, δ, ppm: 2.35 s (3Н, Ме),
.91 s (2Н, СН ), 7.11 br.s (1Н, NН ), 7.22 d (2Н,
2
2
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