2-(4-nitrophenyl)oxirane amino derivatives in heterocyclization reactions

Article abstract of DOI:10.1134/S1070428015080096

Reactions of 2-amino-1-(4-nitrophenyl)ethanol with various electrophilic reagents led to the formation of oxazaheterocycles (1,3-oxazolidin-2-one, 1,3-oxazolidine, morpholin-2-, -3-one, and -2,3-dione). In reactions of 2-{(bicyclo[2.2.1]hept-5-en-2-ylmeth

Full text of DOI:10.1134/S1070428015080096

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 8, pp. 1114–1118. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © V.A. Pal’chikov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1135–1139.
2-(4-Nitrophenyl)oxirane Amino Derivatives
in Heterocyclization Reactions
V. A. Pal’chikov
Oles’ Honchar Dnepropetrovsk National University, pr. Gagarina 72, Dnepropetrovsk, 49010 Ukraine
e-mail: palchikoff@mail.ru
Received June 17, 2015
Abstract—Reactions of 2-amino-1-(4-nitrophenyl)ethanol with various electrophilic reagents led to the
formation of oxazaheterocycles (1,3-oxazolidin-2-one, 1,3-oxazolidine, morpholin-2-, -3-one, and -2,3-dione).
In reactions of 2-{(bicyclo[2.2.1]hept-5-en-2-ylmethyl)amino}-1-(4-nitrophenyl)ethan-1-ol with carbonyldiimi-
dazole, oxalyl chloride, benzaldehyde, and formaldehyde the corresponding derivatives of 1,3-oxazolidin-2-
one, morpholin-2,3-dione, and 1,3-oxazolidine were obtained.
DOI: 10.1134/S1070428015080096
Among the numerous epoxy compounds a special
place belongs to 4-nitrostyrene oxide 1 [2-(4-
nitrophenyl)oxirane]. The structural fragment of 4-
nitrophenyloxirane is a very prospective scaffold
existing in many biologically active substances,
antibiotics, vasodilators, herbicides, plant growth
regulators [1]. The most well-known pharmaceuticals
are antibiotic chloramphenicol 2 [levomycetin, D-(–)-
threo-1-(4-nitrophenyl)-2-(dichloroacetylamino)propa-
ne-1,3-diol], and its racemate synthomycine [2–4], and
also β-adrenoblockers d-(+)-sotalol 3 and (R)-nifenalol
4 possessing antianginal, antiarrhythmic, and hypoten-
sive action [5–9].
Here we report on an extension of the investigation
in the field of aminoalcohols synthesis and their
functionalization at the alternative nucleophilic centers
(the preparation of N-acyl, N-sulfonyl, O-silyl, О-acyl
derivatives) [13, 14]. We studied the possibility of
aminoalcohols heterocyclization into five- and six-
membered nonaromatic 1,3- and 1,4-oxazahetero-
cycles, whose practical importance had been widely
described in [15–18]. Some of the obtained compounds
include a secondary amine or amide moiety, which
increases their synthetic potential and enables them to
participate in the development of combinatorial
libraries of new compounds via subsequent acylation
and alkylation at the nitrogen atom.
OH
OH
O
We selected as the starting material 2-amino-1-(4-
nitrophenyl)ethanol 5 [19, 20]. Its reactions with
various cyclization agents led to the obtaining of a
number of simplest oxazaheterocyclic derivatives 6–
10. 1,3-Oxazolidin-2-one 6 is formed by the action of
carbonyldiimidazole (СDI) on the starting aminoalco-
hol, or in interaction with dimethyl carbonate. In the
latter case the yield reached 60%. The methods known
before [heating of 2-(4-nitrophenyl)oxirane 1 with urea
above the melting point in solvent free conditions, or
refluxing starting materials in DMF] afforded
compound 6 in 7–30% yields [21], moreover
regioisomeric oxazolidinone 6' is formed as a by-
product. The microwave irradiation of the mixture of
aminoalcohol 5 with urea in nitromethane as described
in [22] does not lead to the desired product 6 and the
Cl
HN
O2N
Cl
O2N
1
2
O
OH
OH
H
N
H
N
.
HCl
O2N
MsHN
4
3
The recent studies of our scientific team revealed
the analgesic, anticonvulsant, tranquillizing activity of
cage sulfonamides and aminoalcohols including a 4-
nitrophenyl fragment [10–12].
1114

2-(4-NITROPHENYL)OXIRANE AMINO DERIVATIVES IN HETEROCYCLIZATION
1115
Scheme 1.
O
2 equiv Me2CO3, MeONa
O
PhH, reflux, 6 h, 60%
NH
2 equiv EtO2C_CO2Et
OH
O
1 equiv CDI, CHCl3
24 h, 20oC, 41%
H
N
EtOH, reflux,
1.5 h
O2N
O
6
(NH2)2CO, MW (800 W)
MeNO2, 10 min
J 6.0 Hz
O
O
NO2
11
O
O2N
EtOH,
H
2
+
H
O1
N
O
6
3 N
5
37% aq. CH2O (excess)
12 h, 20oC
4
reflux,
OH
7 h
2
5
O
1
6
3
4
NH2
7, 79%
O2N
NH
O
O2N
2
5
O1
6
3
O2N
5
O
(40% aq.)
O
10, 94%
4NH
O
THF, 6 h, reflux
J 10_13 Hz
NO2
8, 66%
O
NH
O2N
H
O
H
N
N
O
2
1. 1 equiv NEt3, 1 equiv ClCH2C(O)Cl,
MeCN, _10oC, 18 h
O1
3
O
4NH
6
5
2. 2.5 equiv t-BuOK, t-BuOH, 40oC, 3 h;
then HCl
O2N
NO2
6'
7'
O2N
9, 61%
starting aminoalcohol was recovered nearly quantita-
tively. The reaction of compound 5 with formaldehyde
yielded bisoxazolidine 7. The formation of compound
7 is confirmed by the value of the heminal spin-spin
coupling constant of the protons of the OCH2N group
(2J2A,2B 6 Hz). According to published data in the
alternative isomer of the structure of 1,6-diaza-3,8-
dioxabicyclo[4.4.1]undecane 7' this coupling constant
should by of 10–13 Hz [23, 24]. Besides the formation
of similar bis-products in analogous conditions was
mentioned in [25, 26]. Morpholin-2- and -3-ones 8 and
9 were obtained by procedures [27, 28]. The reaction
of excess diethyl oxalate with compound 5 first gave
the oxalic acid amidoester 11 (data of 1Н NMR
spectrum). After 1.5 h of boiling reagents the ratio of
compounds 10 and 11 was 1 : 2, at longer reaction we
isolated only the derivative of morpholin-2,3-dione 10
(Scheme 1).
Since the oxazaheterocyclic derivatives of cage
aminoalcohols almost have not been studied [15–18],
some of the above described synthetic methods were
tested on aminoalcohol 12 including a norbornene
fragment. Aminoalcohol 12 was less active than its
analog 5. The reaction with diethyl oxalate resulted in
Scheme 2.
7
4
5
3
NO2
2
1.5 equiv (COCl)2, 4 equiv Et3N
1
6
1 equiv CDI, CHCl3
24 h, 20oC
20oC
8
5 mol% DMAP, CH2Cl2, 0
N
NO2
N
O
O
O
O
15, 33%
O
14, 50%
NO2
1 equiv PhCHO
PhMe, reflux, 6 h
2 equiv EtO2C_CO2Et
EtOH, reflux, 8 h
NO2
NO2
N
O
N
H
Ph
N
16, 73%
OH
O
OH
O
12
O
13, 63%
37% aq. CH2O (excess)
12 h, 20oC
NO2
N
O
17, 71%
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 8 2015

PAL’CHIKOV
1116
amide 13, but further cyclization into morpholin-2,3-
dione 14 did not occur even after 36 h of boiling.
Compound 14 formed only under the action of oxalyl
chloride in the presence of a catalytic quantity of 4-
dimethylaminopyridine. By reactions of aminoalcohol
12 with CDI, benzaldehyde, and formaldehyde we
obtained the corresponding derivatives of 1,3-oxa-
zolidin-2-one and 1,3-oxazoli-dine 15–17 (Scheme 2).
cohol 12 [29] and 0.28 g (1.73 mmol) of carbonyldi-
imidazole. Yield 0.18 g (33%), mp 165–167°С. IR
spectrum, cm–1: 3445, 1750, 1515, 1445, 1350, 1255,
1
720. Н NMR spectrum (CDCl3), δ, ppm: 0.55 m (1Н,
2
Н3n), 1.23 d (1H, H7a, J7s,7a 8.1 Hz), 1.43 d (1H, H7s),
1.85 m (1Н, Н3х), 2.20 m (1Н, Н2), 2.71 m (2Н, Н8),
2.78 m (1Н, Н4), 2.83 m (1Н, Н1), 3.40 m (1Н, NCH2),
4.05 m (1Н, NCH2), 5.80 m (1Н, OCH), 5.90 d.d (1Н,
3
3
3
Н5, J5,6 6.0, J4,5 2.9 Hz), 6.15 d.d (1Н, Н6, J5,6 6.0,
The structure of obtained compounds is confirmed
3J1,6 3.1 Hz), 7.67 d (2Нarom, J 8.7 Hz), 8.20 d (2Нarom
,
by 1Н NMR and IR spectra.
J 8.7 Hz). Found, %: C 65.25; H 5.52; N 9.17.
C17H18N2O4. Calculated, %: C 64.96; H 5.77; N 8.91.
EXPERIMENTAL
Bis[5-(4-nitrophenyl)oxazolidin-3-yl]methane
(7). To 0.25 g (1.37 mmol) of aminoalcohol 5 was
added 5 mL of 37% water solution of formaldehyde.
The reaction mixture was stirred at 20°С for 12 h, solid
sodium hydrogen carbonate was added to reach weak
alkaline reaction, the reaction product was extracted
into dichloromethane (3 × 20 mL). The organic layer
was dried with sodium sulfate, evaporated in a
vacuum, the residue was recrystallized from a mixture
ethyl acetate–hexane. Yield 0.22 g (79%), mp 120–
122°С. IR spectrum, cm–1: 3030, 2880, 1595, 1345,
IR spectra were recorded on a spectrophotometer
Spectrum One (Perkin Elmer) using KBr pellets. Н
1
NMR spectra were registered on Varian and Bruker spec-
trometers at operating frequencies 400 and 500 MHz
with TMS as internal reference. The reaction progress
was monitored and the purity of obtained compounds
was checked by TLC on Silufol 60F254 plates, eluent
ethyl acetate–hexane; the plates were visualized with
iodine vapor. Elemental analysis was performed using
Carlo Erba analyzer. Spectral characteristics of com-
pound 6 were in correspondence with the literature
[21].
1
1190. Н NMR spectrum (CDCl3), δ, ppm: 2.88 d.d
2
3
(2Н, H4А, J4А,4B 11.8, J5,4А 7.5 Hz), 3.55 s (2H, H6),
3.59 d.d (2Н, H4B, J4А,4B 11.8, J5,4B 6.5 Hz), 5.05 d
2
3
5-(4-Nitrophenyl)oxazolidin-2-one (6). а. To a
solution of 0.50 g (2.74 mmol) of 2-amino-1-(4-nitro-
phenyl)ethanol 5 in 20 mL of anhydrous benzene was
added 0.49 g (0.46 mL, 5.49 mmol) of dimethyl
carbonate and 0.015 g (0.27 mmol, 10 mol %) of
sodium methylate. The reaction mixture was boiled for
6 h, the solvent was removed in a vacuum, the residue
was treated with water, neutralized with hydrochloric
acid solution, the precipitate was filtered off and
recrystallized from a mixture ethyl acetate–hexane.
Yield 0.34 g (60%), mp105–107°С (decomp.) (mp
110°С [27, 28]).
(2Н, H2А, J2А,2B 6.0 Hz), 5.15 d (2Н, H2B, J2А,2B
6.0 Hz), 5.33 m (2Н, H5), 7.65 d (4Нarom, J 8.7 Hz),
8.20 d (4Нarom, J 8.7 Hz). Found, %: C 57.25; H 5.22;
N 13.88. C19H20N4O6. Calculated, %: C 57.00; H 5.04;
N 13.99.
2
2
3-{(Bicyclo[2.2.1]hept-5-en-endo-2-yl)methyl}-5-
(4-nitrophenyl)oxazolidine (17) was similarly ob-
tained from 0.50 g (1.73 mmol) of aminoalcohol 12
[29]. Yield 0.37 g (71%), mp 153–156°С. IR spectrum,
1
cm–1: 3045, 1715, 1525, 1420, 1125, 720. Н NMR
spectrum (CDCl3), δ, ppm: 0.75 m (1Н, Н3n), 1.30 d
2
(1H, H7a, J7s,7a 8.1 Hz), 1.42 d (1H, H7s), 1.71 m (1Н,
b. To a solution of 0.30 g (1.65 mmol) of 2-amino-
1-(4-nitrophenyl)ethanol 5 in 10 mL of chloroform was
added 0.27 g (1.7 mmol) of carbonyldiimidazole (СDI).
The reaction mixture was stirred at 20°С for 24 h,
washed with 33% water solution of citric acid (10 mL),
then with water (2 × 15 mL). The organic layer was
dried with sodium sulfate, evaporated in a vacuum, the
residue was recrystallized from a mixture ethyl acetate–
hexane. Yield 0.14 g (41%), mp 106–108°С (decomp.).
Н3х), 2.00 m (1Н, Н2), 2.80–2.95 (4Н, Н1,4,8), 4.01 m
2
(2Н, NCH2СН), 4.50 d (1Н, NCH2О, J 6.1 Hz), 4.89
2
d (1Н, NCH2О, J 6.1 Hz), 5.15 m (1Н, OCHСН2),
3
3
6.05 d (1Н, Н5, J5,6 6.0 Hz), 6.20 d (1Н, Н6, J5,6
6.0 Hz), 7.69 d (2Нarom, J 8.7 Hz), 8.18 d (2Нarom, J
8.7 Hz). Found, %: C 68.21; H 6.50; N 9.11.
C17H20N2O3. Calculated, %: C 67.98; H 6.71; N 9.33.
6-(4-Nitrophenyl)morpholin-2-one (8). To a solu-
tion of 0.50 g (2.74 mmol) of aminoalcohol 5 in 30 mL
of tetrahydrofuran was added 1.19 g (8.22 mmol) of
40% water glyoxal solution. The reaction mixture was
3-{(Bicyclo[2.2.1]hept-5-en-endo-2-yl)methyl}-5-
(4-nitrophenyl)oxazolidin-2-one (15) was obtained
by procedure b from 0.50 g (1.73 mmol) of aminoal-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 8 2015

2-(4-NITROPHENYL)OXIRANE AMINO DERIVATIVES IN HETEROCYCLIZATION
1117
boiled for 6 h, poured into water (20 mL), the reaction
product was extracted into dichloromethane (3 × 30 mL).
Combined organic extracts were dried with sodium
sulfate, evaporated, the residue was chromatographed
on a column packed with silica gel (eluent hexane–ethyl
acetate, 1 : 1). Yield 0.40 g (66%), mp 156–159°С
(decomp.). IR spectrum, cm–1: 3240, 3060, 1750, 1600,
208°С (decomp.). IR spectrum, cm–1: 3240, 3060,
1
1750, 1690, 1440, 1120. Н NMR spectrum (DMSO),
δ, ppm: 3.35 m (2H, H5), 4.87 m (1H, H6), 7.59 d
(2Нarom, J 8.5 Hz), 8.19 d (2Нarom, J 8.5 Hz), 8.60 br.s
(1Н, NH). Found, %: C 50.71; H 3.60; N 12.07.
C10H8N2O5. Calculated, %: C 50.85; H 3.41; N 11.86.
Ethyl 2-{[(bicyclo[2.2.1]hept-5-en-endo-2-yl)-me-
thyl][2-hydroxy-2-(4-nitrophenyl)ethyl]amino}-2-
oxoacetate (13) was obtained by the same procedure
from 0.50 g (1.73 mmol) of aminoalcohol 12 [29] and
0.51 g (0.47 mL, 3.47 mmol) of diethyl oxalate. Yield
0.42 g (63%), mp 183–185°С (decomp.). IR spectrum,
cm–1: 3408, 3370, 3060, 1745, 1640, 1520, 1340, 1150,
1
1340, 1150. Н NMR spectrum (CDCl3), δ, ppm: 1.65
br.s (1Н, NH), 3.25–3.35 m (4Н, Н3,5), 5.71 m (1Н, H6),
7.64 d (2Нarom, J 8.6 Hz), 8.21 d (2Нarom, J 8.6 Hz).
Found, %: C 54.25; H 4.32; N 12.80. C10H10N2O4.
Calculated, %: C 54.05; H 4.54; N 12.61.
6-(4-Nitrophenyl)morpholin-3-one (9). To a solu-
tion of 0.50 g (2.74 mmol) of aminoalcohol 5 in 30 mL
of acetonitrile was added at cooling to –10°С 0.28 g
(0.38 mL, 2.74 mmol) of triethylamine, 0.31 g (0.22 mL,
2.74 mmol) of chloroacetyl chloride, and the reaction
mixture was stirred at this temperature for 1 h and then
at room temperature for 18 h. The reaction mixture
was concentrated in a vacuum and subjected to column
chromatography on silica gel (eluent hexane–ethyl
acetate, 1 : 1). Yield of N-acyl derivative 0.57 g (80%),
light-yellow oil. A solution of 0.50 g (1.93 mmol) of
N-acyl derivative in 15 mL of tert-butanol was added
dropwise to a solution of 0.54 g (4.83 mmol) of potas-
sium tert-butylate in 10 mL of tert-butanol at 40°С.
The reaction mixture was stirred at this temperature for
3 h. The solution was acidified to рН 2–3 by adding
2 M solution of НСl and then it was concentrated in a
vacuum. The residue was dispersed in water (100 mL),
the reaction product was extracted into ethyl acetate
(4 × 70 mL), The extract was dried with sodium sulfate
and concentrated in a vacuum. After column
chromatography on silica gel (eluent ethyl acetate) we
obtained 0.37 g of compound 9 (61% calculated for 2
stages), mp 230–233°С. IR spectrum, cm–1: 3240,
1
725. Н NMR spectrum (CDCl3), δ, ppm: 0.52 m (1Н,
2
Н3n), 1.23 d (1H, H7a, J7s,7a 8.1 Hz), 1.30 t (3Н, СН3,
3J 7.5 Hz), 1.44 d (1H, H7s), 1.85 m (1Н, Н3х), 2.20 m
(1Н, Н2), 2.71 m (2Н, Н8), 2.79 m (1Н, Н4), 2.83 m
(1Н, Н1), 3.46 m (1Н, NCH2), 4.12 m (1Н, NCH2),
3
4.26 q (2Н, СН2, J 7.0 Hz), 5.50 m (1Н, OCH), 5.91
3
3
d.d (1Н, Н5, J5,6 5.6, J4,5 3.0 Hz), 6.16 d.d (1Н, Н6,
3J5,6 5.6, 3J1,6 3.0 Hz), 7.65 d (2Нarom, J 8.6 Hz), 8.19 d
(2Нarom, J 8.6 Hz). Found, %: C 62.09; H 6.04; N
7.43. C20H24N2O6. Calculated, %: C 61.85; H 6.23; N
7.21.
4-{(Bicyclo[2.2.1]hept-5-en-endo-2-yl)methyl}-6-
(4-nitrophenyl)morpholine-2,3-dione (14). To a
solution of 0.5 g (1.73 mmol) of aminoalcohol 12 [29]
and 0.01 g (5 mol %) of 4-dimethylaminopyridine in
dichloromethane (50 mL) at 0°С was added while
stirring 0.70 g (0.96 mL, 6.92 mmol) of triethylamine.
The mixture was stirred for 10 min, and then a solution
of 0.33 g (2.60 mmol) of oxalyl chloride in dichlo-
romethane (50 mL) was added dropwise within 4 h at
0°С. After adding the total amount of the reagent the
reaction mixture was stirred additionally for 2 h at 0°С
and warmed to the room temperature. The dichlo-
romethane layer was washed with water (50 mL), dried
with sodium sulfate, and evaporated in a vacuum. The
reaction product was chromatographed on a column
packed with silica gel (eluent hexane–ethyl acetate, 1 : 1).
Yield 0.30 g (50%), mp 199–203°С. IR spectrum, cm–1:
1
3060, 1665, 1340, 1150. Н NMR spectrum (DMSO),
2
3
δ, ppm: 3.35 d.d (1Н, H5B, J5А,5B 8.0, J6,5B 7.0 Hz),
4.05 m (1Н, H5А), 4.33 m (2Н, H2), 4.71 d.d (1Н, H6,
3J6,5А 8.1, 3J6,5B 7.0 Hz), 7.60 d (2Нarom, J 8.7 Hz), 8.00
br.s (1Н, NH), 8.20 d (2Нarom, J 8.7 Hz). Found, %: C
54.31; H 4.60; N 12.33. C10H10N2O4. Calculated, %: C
54.05; H 4.54; N 12.61.
1
3030, 1750, 1690, 1515, 1340, 1150, 720. Н NMR
spectrum (CDCl3), δ, ppm: 0.52 m (1Н, Н3n), 1.23 d
2
6-(4-Nitrophenyl)morpholine-2,3-dione (10). To
a solution of 0.50 g (2.74 mmol) of aminoalcohol 5 in
20 mL of ethanol was added 0.80 g (0.75 mL, 5.49 mmol)
of diethyl oxalate. The reaction mixture was boiled for
8.5 h (TLC monitoring), evaporated in a vacuum, the
residue was treated with ethyl ether, the formed
crystals were filtered off. Yield 0.61 g (94%), mp 205–
(1H, H7a, J7s,7a 8.1 Hz), 1.44 d (1H, H7s), 1.85 m (1Н,
Н3х), 2.20 m (1Н, Н2), 2.70 m (2Н, Н8), 2.81 m (1Н,
Н4), 2.83 m (1Н, Н1), 3.46 m (1Н, NCH2), 4.12 m (1Н,
NCH2), 5.60 m (1Н, OCH), 5.93 m (1Н, Н5), 6.19 m
(1Н, Н6), 7.65 d (2Нarom, J 8.6 Hz), 8.19 d (2Нarom, J
8.6 Hz). Found, %: C 62.99; H 5.04; N 7.91.
C18H18N2O5. Calculated, %: C 63.15; H 5.30; N 8.18.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 8 2015

PAL’CHIKOV
1118
10. Zlenko, H.T., Palchikov, V.A., and Rybalko, V.E., Eur.
Psych., 2012, vol. 27, p. 913.
11. Zlenko, H.T., Palchikov, V.A., and Tretjakov, S.V.,
3-{(Bicyclo[2.2.1]hept-5-en-endo-2-yl)methyl}-5-
(4-nitrophenyl)-2-phenyloxazolidine (16). A slurry
of 0.50 g (1.73 mmol) of aminoalcohol 12 [29], 0.18 g
(1.73 mmol) of benzaldehyde, and 0.50 g of anhydrous
sodium sulfate in 25 mL of anhydrous toluene was
boiled for 6 h. The toluene solution was filtered while
hot. On removing the solvent the reaction product was
recrystallized from 2-propanol. Yield 0.48 g (73%),
mp 133–135°С. IR spectrum, cm–1: 3030, 1715, 1530,
Eur. J. Pain Suppl., 2011, vol. 5, p. 90.
12. Palchikov, V.A., Kasyan, L.I., Zlenko, H.T.,
Golodayeva, H.A., Pryshlyak, I.S., and Turov, A.V.,
Drugs Fut., 2010, vol. 35 (A), p. 155.
13. Kas'yan, L.I., Golodaeva, E.A., Kas'yan, A.O., and
Isaev, A.K., Russ. J. Org. Chem., 2003, vol. 39, p. 1398.
14. Kas'yan, L.I., Golodaeva, E.A., and Kas'yan, A.O.,
1
1410, 1124, 720. Н NMR spectrum (CDCl3), δ, ppm:
2
0.65 m (1Н, Н3n), 1.30 d (1H, H7a, J7s,7a 8.0 Hz), 1.43
Russ. J. Org. Chem., 2003, vol. 39, p. 1248.
15. Pal’chikov, V.A., Russ. J. Org. Chem., 2013, vol. 49,
d (1H, H7s), 1.79 m (1Н, Н3х), 2.10 m (1Н, Н2), 2.85 m
(1Н, Н1), 2.95 m (1Н, Н4), 3.21 m (2Н, Н8), 4.41 m
(2Н, NCH2), 5.15 m (1Н, OCHСН2), 5.70 m (1Н,
p. 787.
16. Kas’yan, L.I., Pal’chikov, V.A., and Bondarenko, Ya.S.,
Russ. J. Org. Chem., 2011, vol. 47, p. 1609.
17. Kas’yan, L.I., Pal’chikov, V.A., and Bondarenko, Ya.S.,
Russ. J. Org. Chem., 2011, vol. 47, p. 797.
18. Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org.
Chem., 2010, vol. 46, p. 1.
3
OCHN), 5.95 d (1Н, Н5, J5,6 6.0 Hz), 6.19 d (1Н, Н6,
3J5,6 6.0 Hz), 7.35 m (5Нarom), 7.68 d (2Нarom, J 8.7 Hz),
8.18 d (2Нarom, J 8.7 Hz). Found, %: C 73.51; H 6.31;
N 7.11. C23H24N2O3. Calculated, %: C 73.38; H 6.43;
N 7.44.
19. Gupta, P., Rouf, A., Shah, B.A., Mukherjee, D., and
Taneja, S.C., Synth. Commun., 2013, vol. 43, p. 505.
20. Lebel, H., Parmentier, M., Leogane, O., Ross, K., and
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