Some chemical transformations of alkyl (4-aminophenyl)carbamates

Article abstract of DOI:10.1134/S1070428013070087

Azo coupling of diazonium salts derived from alkyl (4-aminophenyl) carbamates with ethyl α-methylacetoacetate gave ethyl 5- alkoxycarbonylamino-1H-indole-2-carboxylates. The condensation of aminophenylcarbamates with aromatic aldehydes in ethanol afforded

Full text of DOI:10.1134/S1070428013070087

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 7, pp. 1004–1009. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © A.V. Velikorodov, V.A. Ionova, S.I. Temirbulatova, M.A. Suvorova, 2013, published in Zhurnal Organicheskoi Khimii, 2013,
Vol. 49, No. 7, pp. 1020–1025.
Some Chemical Transformations of Alkyl
(4-Aminophenyl)carbamates
A. V. Velikorodov, V. A. Ionova, S. I. Temirbulatova, and M. A. Suvorova
Astrakhan State University, pl. Shaumyana 1, Astrakhan 414000 Russia
e-mail: avelikorodov@mail.ru
Received October 11, 2012
Abstract—Azo coupling of diazonium salts derived from alkyl (4-aminophenyl)carbamates with ethyl
α-methylacetoacetate gave ethyl 5-alkoxycarbonylamino-1H-indole-2-carboxylates. The condensation of
aminophenylcarbamates with aromatic aldehydes in ethanol afforded the corresponding Schiff bases. Cyclo-
hexyl {4-[(4-methoxyphenyl)methylidene]aminophenyl}carbamate reacted with chloroacetyl chloride in diox-
ane in the presence of triethylamine to produce cyclohexyl {4-[3-chloro-2-(4-methoxyphenyl)-4-oxoazetidin-1-
yl]phenylcarbamate, and the reaction of benzyl {4-[(4-nitrophenyl)methylidene]aminophenyl}carbamate with
sulfanylacetic acid in DMF led to the formation of benzyl {4-[2-(4-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]-
phenyl}carbamate.
DOI: 10.1134/S1070428013070087
Aromatic and heteroaromatic amines attract much
interest as important intermediate products in the syn-
thesis of various aromatic and heterocyclic compounds
[1–4]. Amino derivatives of alkyl phenylcarbamates
were synthesized previously by reduction of the corre-
sponding alkyl (4-nitrosophenyl)carbamates with
sodium dithionite [5]. It was also shown [5] that the
Japp–Klingemann–Fischer reaction with benzyl and
cyclohexyl (4-aminophenyl)carbamates I and II yields
carbamate derivatives of indoles having no substituents
in positions 1 and 3. The azo coupling with ethyl
α-methylacetoacetate was carried out with arenediazo-
nium chlorides and p-toluenesulfonates obtained by
diazotization of aminophenylcarbamates I and II with
nitrous acid and polymeric diazotizing agent
[Polym]+ NO2–. In the latter case, the diazotization was
performed by adding polymeric diazotizing agent
(prepared by saturation of AV-17-8 anion exchanger
with nitrite ions [6]) and alkyl (4-aminophenyl)carba-
mate I or II to a solution of p-toluenesulfonic acid in
glacial acetic acid.
Unlike diazotization with nitrous acid, the reaction
–
with [Polym]+ NO2 was complete in 30 min at room
temperature, and the diazotization products were
isolated as individual substances by precipitation with
diethyl ether after separation of the anion exchanger
by filtration. As shown in [7], diazotization with
[Polym]+ NO2– of aromatic amines having electron-
withdrawing substituents in the benzene ring gives the
corresponding arenediazonium p-toluenesulfonates,
whereas aromatic amines with electron-donating
groups are converted into (Z)-1-aryl-2-tosyldiazenes
Scheme 1.
NHCOOR
TsOH, [Polym]+ NO2, AcOH
TsO– N2
NHCOOR
IIIa, IVa
H2N
NHCOOR
I, II
N
TsO
N
I, IIIa, R = PhCH2; II, IVa, R = cyclo-C6H11.
1004

SOME CHEMICAL TRANSFORMATIONS OF ALKYL (4-AMINOPHENYL)CARBAMATES
1005
Scheme 2.
NHCOOR
O
O
O
O
NHCOOR
OH–
Me
N
+
EtO
N
Me
OEt
X– N2
IIIa, IIIb, IVa, IVb
Me
Me
A
NHCOOR
NHCOOR
O
O
OH–
–AcONa
N
N
EtO
N
EtO
N
H
Me
Me
B
C
NHCOOR
H
H
O
RO
N
RO
N
O
COOEt
NH2
H+
H+
H
N
EtO
N
O
O
–NH3
N
N
OEt
H
H
H
CH2
C
D
V, VI
X = TsO (a), Cl (b).
which can also be involved in azo coupling. We have
found that, despite electron-donor properties of al-
koxycarbonylamino group, the diazotization of I and II
with [Polym]+ NO2– yields arenediazonium p-toluene-
sulfonates IIIa and IVa (Scheme 1).
be determined by the ability of the latter to undergo
acid-catalyzed tautomeric transformation into imidoyl
structure which acts as a weak electron acceptor.
Arenediazonium p-toluenesulfonates IIIa and IVa
and the corresponding chlorides IIIb and IVb were
brought into azo coupling with ethyl α-methylaceto-
acetate in alkaline medium (Scheme 2). Initially
formed azo coupling product A underwent acid
decomposition by the action of concentrated alkali to
give azo compound B. Unlike common acid decom-
position of β-keto esters, no hydrolysis of the ester
group occurred; moreover, the carbamate moiety also
remained unchanged. Passing of dry hydrogen chloride
through a solution of azo compound B in anhydrous
ethanol induced isomerization to enamine C which
underwent acid-catalyzed cyclization to indole V or VI
via elimination of ammonia molecule from inter-
mediate D. The structure of V and VI was confirmed
by their IR and 1H NMR spectra.
The formation of diazonium salts IIIa and IVa
follows from their IR, 13C NMR, and mass spectra.
Apart from other bands, the IR spectra of IIIa and IVa
contained a medium-intensity absorption band at
2276–2280 cm–1 due to stretching vibrations of the
13
N≡N+ group. In the C NMR spectra of IIIa and IVa
the signal of the carbon atom bearing the diazonium
group was observed at δC 112.42 and 111.12 ppm,
respectively, due to magnetic anisotropy of the N≡N
group. If these compounds contained an N=N bond,
the signal from the neighboring aromatic carbon atom
would appear in a weaker field (δC 120–131 ppm) [7].
The mass spectra of IIIa and IVa revealed no molec-
ular ion peaks because of low volatility of arenediazo-
nium p-toluenesulfonates, but ion peaks corresponding
to thermal decomposition products formed as a result
of loss of nitrogen molecule were present [8, 9].
Primary aromatic amines are widely used to prepare
Schiff bases exhibiting a great pharmacological poten-
tial. Compounds possessing anticonvulsant [10],
cardiotonic [11], antiproliferative [12], antifungal [13],
antitumor [14], and antimicrobial activity [15] were
The observed pattern in the diazotization of
aromatic amines having a carbamate group is likely to
Scheme 3.
NHCOOR
NHCOOR
EtOH, Δ
+
ArCHO
H2N
Ar
N
I, II
VII–IX
VII, VIII, R = Ph CH2; IX, R = cyclo-C6H11; VII, Ar = 4-O2NC6H4; VIII, Ar = 2,4-(HO)2C6H3; IX, Ar = 4-MeOC6H4.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 7 2013

VELIKORODOV et al.
1006
Scheme 4.
MeO
H
N
H
ClCH2COCl, Et3N
dioxane, Δ
O
N
O
O
O
4-MeOC6H4
N
N
Cl
O
IX
X
Scheme 5.
O2N
H
N
HSCH2COOH
Ph
H
N
O
O
Ph
DMF, Δ
O
O
4-O2NC6H4
N
N
S
O
VII
XI
found among Schiff bases. They are also used as inter-
mediate products in the synthesis of various biologi-
cally active compounds, in particular thiazolidinone,
azetidinone, formazan, arylacetamide, and many other
derivatives [16–18].
a period of 12 h to produce thiazolidinone derivative
XI (Scheme 5). Unlike initial Schiff base VII, the IR
spectrum of XI lacked absorption band at 1645 cm–1
assignable to C=N stretching vibrations, but a band at
687 cm–1 appeared due to stretching vibrations of the
C–S–C fragment; in addition, a carbonyl absorption
band was present at 1780 cm–1 [ν(C=O) in the thiazoli-
dine ring] together with the carbamate carbonyl band
at 1710 cm–1. Singlets at δ 4.15 (2H) and 5.32 ppm
With a view to obtain potentially biologically active
Schiff bases having a carbamate functionality, alkyl
(4-aminophenyl)carbamates I and II were brought into
condensation with aromatic aldehydes in ethanol in the
presence of a catalytic amount of glacial acetic acid
(Scheme 3). As expected, the products were the
corresponding Schiff bases VII–IX. Unlike the initial
compounds, the IR spectra of VII–IX contained an ab-
sorption band at 1645–1650 cm–1 due to stretching
vibrations of the C=N bond. Apart from other signals,
1
(1H) in the H NMR spectrum of XI were assigned to
the C5H2 methylene group and 2-H proton in the thia-
zolidine ring.
Thus the described transformations of alkyl amino-
phenylcarbamates demonstrate a wide potential for
their functionalization with formation of new com-
pounds that are promising from the viewpoint of their
biological activity.
1
Schiff base VII displayed in the H NMR spectrum
a one-proton singlet at δ 8.82 ppm from the azo-
methine proton.
The reaction of Schiff base IX with chloroacetyl
chloride in the presence of triethylamine in boiling
dioxane (12 h) afforded cyclohexyl {4-[3-chloro-2-(4-
methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}carbamate
(X) (Scheme 4) whose structure was determined by IR
and H NMR spectroscopy. In the H NMR spectrum
of X we observed singlets at δ 5.70 ppm from 2-H and
at δ 4.89 ppm from 3-H in the azetidine ring, which is
consistent with published data for structurally related
azetidine derivatives [1, 2].
EXPERIMENTAL
1
The H NMR spectra were recorded on a Bruker
DRX-500 spectrometer at 500.13 MHz using tetra-
methylsilane as internal reference. The 13C NMR spec-
tra were measured with complete decoupling from
protons on a Bruker WM-400 instrument at 100 MHz
using DMSO-d6 as solvent. The IR spectra were
recorded in the range from 4000 to 400 cm–1 on
an InfraLUM FT-02 spectrometer with Fourier trans-
form from samples prepared as KBr pellets. The mass
spectra (electron impact, 70 eV) were obtained on
1
1
Compound VII reacted with sulfanylacetic acid on
heating in boiling anhydrous dimethylformamide over
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SOME CHEMICAL TRANSFORMATIONS OF ALKYL (4-AMINOPHENYL)CARBAMATES
1007
a Finnigan MAT INCOS 50 instrument. The purity of
the isolated compounds was checked by TLC on
Silufol UV-254 plates; spots were visualized by treat-
ment with iodine vapor.
Polymeric diazotizing agent [Polym]+ NO2–.
Sodium nitrite, 2.07 g (30 mmol), was dissolved in
30 ml of distilled water, 3.5 g of AV-17-8 anion ex-
changer (an analog of Amberlyst A26) was added, the
mixture was stirred for 10 min, and the exchanger was
filtered off and washed with distilled water until
neutral washings. The resulting polymeric diazotizing
agent contained 3.5 mmol of nitrite ions per gram,
which is consistent with the data of [6, 7].
Ethyl 5-benzyloxycarbonylamino-1H-indole-2-
carboxylate (V). a. A solution of 1.54 g (0.01 mol) of
ethyl α-methylacetoacetate in 1 ml of dioxane was
cooled to 0°C, 3.5 ml of cold 50% aqueous potassium
hydroxide was added, the mixture was diluted with
water (20 ml), 4.3 g (0.01 mol) of diazonium salt IIIa
was quickly added under stirring, and the mixture was
stirred for 5 min. The aqueous phase was extracted
with diethyl ether (2×15 ml), the combined extracts
were dried over sodium sulfate, the solvent was dis-
tilled off under reduced pressure, the residue was dis-
solved in anhydrous ethanol, dry hydrogen chloride
was passed through the solution until ammonium
chloride began to separate therefrom, and the mixture
was left overnight. The mixture was then poured into
ice water, and the crystalline product was filtered off,
dried in air, and recrystallized from ethanol. Yield
2.10 g (63%), light brown crystals, mp 168–169°C. IR
spectrum, ν, cm–1: 3330–3310 (NH), 1710, 1680
Arenediazonium p-toluenesulfonates IIIa and
IVa (general procedure). To a solution of p-toluene-
sulfonic acid in acetic acid we added 1 g of
[Polym]+ NO2– and 1.2 mmol of aromatic amine I or II,
and the mixture was stirred for 10 min. The precipitate
was filtered off, and the product was isolated from
the filtrate by precipitation with diethyl ether and
dried in air.
1
(C=O), 1620, 1590, 1555 (C=Carom). H NMR spec-
trum (acetone-d6), δ, ppm: 1.32 t (3H, Me, J = 6.8 Hz),
4.20–4.33 m (4H, OCH2), 5.81 s (1H, 3-H), 7.30–
7.65 m (5H, Harom), 7.81 d (1H, Harom, J = 10 Hz),
7.93 d (1H, Harom, J = 10 Hz), 8.10 s (1H, 4-H),
8.37 br.s (1H, NH), 9.50 br.s (1H, NH). Found, %:
C 67.33; H 5.40; N 7.95. C19H18N2O4. Calculated, %:
C 67.46; H 5.33; N 8.28.
4-Benzyloxycarbonylaminobenzenediazonium
p-toluenesulfonate (IIIa). Yield 83%, colorless crys-
tals, mp 169–170°C (decomp.). IR spectrum, ν, cm–1:
3310 (NH), 2276 (N≡N), 1720 (C=O), 1610, 1575,
1
1560 (C=Carom). H NMR spectrum (DMSO-d6), δ,
ppm: 2.29 s (3H, CH3), 5.23 s (2H, CH2Ph), 7.13 d
(2H, Harom, J = 8.5 Hz), 7.15–4.48 m (7H, Harom),
7.92 d (2H, Harom, J = 8.0 Hz), 8.55 d (2H, Harom, J =
8.5 Hz), 11.15 s (1H, NH). 13C NMR spectrum, δC,
ppm: 21.21 (CH3), 68.12 (CH2Ph), 110.60 (2C, Carom),
112.42 (Ci); 125.95, 127.14, 127.74, 127.84, 128.58,
135.90, 136.15, 138.36, 139.95, 143.10 (15C, Carom);
153.93 (C=O). Mass spectrum, m/z (Irel, %): 397 (1)
[M – N2]+ , 333 (1) [M – N2 – SO2]+, 317 (1), 242 (3),
227 (2), 198 (3), 183 (1), 172 (3), 155 (3), 119 (1), 107
(14), 91 (100), 77 (7), 65 (17), 51 (7), 44 (20).
Calculated: M 425.10.
b. Carbamate I, 2.42 g (0.01 mol), was dissolved in
a mixture of 12.6 ml of hot water and 2.5 ml of
20% aqueous HCl, the mixture was cooled to 0–5°C,
and an equal volume of hydrochloric acid was added.
The resulting solution was subjected to diazotization
by adding dropwise under stirring and efficient cooling
a solution of 0.76 g (0.01 mol) of sodium nitrite in
20 ml of water. When the addition was complete, the
mixture was kept for 1 h in the cold. A solution of
1.54 g (0.01 mol) of ethyl α-methylacetoacetate was
cooled to 0°C, 3.5 ml of cold 50% aqueous potassium
hydroxide was added, the mixture was diluted with ice
water (20 ml), the solution of diazonium salt IIIb was
quickly added, and the mixture was stirred for 5 min.
The azo compound was isolated and subjected to
heterocyclization to indole V as described above in a.
Yield 1.76 g (52%), light brown crystals, mp 168–
169°C. Found, %: C 67.39; H 5.35; N 7.99.
C19H18N2O4. Calculated, %: C 67.46; H 5.33; N 8.28.
4-Cyclohexyloxycarbonylaminobenzenediazoni-
um p-toluenesulfonate (IVa). Yield 81%, colorless
crystals, mp 193–195°C (decomp.). IR spectrum, ν,
cm–1: 3310 (NH), 2280 (N≡N), 1720 (C=O), 1610,
1570 (C=Carom). 13C NMR spectrum, δC, ppm: 20.88
(CH3); 23.38, 24.18, 31.54 (5C, CH2); 69.28 (OCH),
111.12 (Ci); 112.56, 125.76, 128.75, 138.95, 139.04,
144.20, 145.78 (11C, Carom); 154.02 (C=O). Mass
spectrum, m/z (Irel, %): 389 (3) [M – N2]+, 325 (1)
[M – N2 – SO2]+, 319 (1), 244 (3), 219 (2), 190 (3),
175 (1), 155 (3), 119 (2), 99 (100), 83 (15), 77 (6), 65
(17), 51 (6), 44 (19). Calculated: M 417.14.
Ethyl 5-cyclohexyloxycarbonylamino-1H-indole-
2-carboxylate (VI). a. Compound VI was synthesized
as described above for V (method a) from 0.42 g
(0.001 mol) of diazonium salt IVa. Yield 0.2 g (61%),
light brown crystals, mp 163–165°C (from CH2Cl2–
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 7 2013

VELIKORODOV et al.
1008
petroleum ether, 1:2 by volume). IR spectrum, ν, cm–1:
2.34 g (0.01 mol) of compound II and 1.36 g
(0.01 mol) of 4-methoxybenzaldehyde. Yield 3.1 g
(89%), yellow crystals, mp 135–137°C (from EtOH–
dioxane, 5:1 by volume). IR spectrum, ν, cm–1: 3315
(NH), 1710 (C=O), 1645 (C=N), 1610, 1595, 1575
(C=Carom). Found, %: C 71.38; H 6.64; N 7.87.
C21H24N2O3. Calculated, %: C 71.59; H 6.82; N 7.96.
3340–3315 (NH), 1710, 1690 (C=O), 1610, 1590,
1
1535 (C=Carom). H NMR spectrum (acetone-d6), δ,
ppm: 1.16–1.47 m (9H, CH2CH3, cyclohexyl), 2.20–
2.27 m and 2.38–2.41 m (2H each, cyclohexyl), 4.40 q
(2H, OCH2, J = 6.7 Hz), 4.90–4.93 m (1H, OCH),
7.04 s (1H, Harom), 7.28 s (1H, 3-H), 7.54 d (1H, Harom
,
J = 7.7 Hz), 8.90 d (1H, Harom, J = 7.7 Hz), 9.53 br.s
(1H, 5-NH), 11.78 br.s (1H, 1-H). Found, %: C 65.43;
H 6.58; N 8.36. C18H22N2O4. Calculated, %: C 65.46;
H 6.67; N 8.49.
Cyclohexyl {4-[3-chloro-2-(4-methoxyphenyl)-4-
oxoazetidin-1-yl]phenyl}carbamate (X). Compound
IX, 1.76 g (5 mmol), was dissolved in 25 ml of
dioxane, 0.4 ml (5 mmol) of chloroacetyl chloride was
added dropwise under continuous stirring at room
temperature, the mixture was stirred for 10 min, 0.7 ml
(5 mmol) of triethylamine was added, and the mixture
was heated for 12 h under reflux, the progress of the
reaction being monitored by TLC. When the reaction
was complete, the mixture was poured into 100 ml of
ice water, and the precipitate was filtered off, washed
with water (20 ml) on a filter, dried in air, and recrys-
tallized from ethanol. Yield 1.63 g (76%), colorless
crystals, mp 158–160°C. IR spectrum, ν, cm–1: 3310
(NH), 1710, 1715 (C=O), 1620, 1585, 1575 (C=Carom).
1H NMR spectrum (DMSO-d6), δ, ppm: 1.12–1.48 m
(6H), 2.20–2.27 m (2H), and 2.37–2.40 m (2H)
(cyclohexyl); 3.31 d (1H, CHCl, J = 1.6 Hz), 3.34 d
(1H, 2-H, J = 5.5 Hz), 3.78 s (3H, OMe), 4.94–4.98 m
(1H, OCH), 6.62 d (1H, Harom, J = 8.7 Hz), 6.65 d (1H,
Harom, J = 8.7 Hz), 7.23 d (1H, Harom, J = 8.7 Hz),
7.33–7.38 m (3H, Harom), 7.53 d (1H, Harom, J =
8.6 Hz), 7.56 d (1H, Harom, J = 8.6 Hz), 9.57 br.s
(1H, NH). Found, %: C 64.28; H 5.62; N 6.39.
C23H25ClN2O4. Calculated, %: C 64.41; H 5.83; N 6.53.
b. The procedure was analogous to that described
above for compound V (method b). Light brown crys-
tals, mp 163–165°C (from CH2Cl2–petroleum ether,
1:2 by volume). Found, %: C 65.48; H 6.56; N 8.34.
C18H22N2O4. Calculated, %: C 65.46; H 6.67; N 8.49.
Benzyl {4-[(4-nitrophenyl)methylidene]amino-
phenyl}carbamate (VII). A mixture of 2.42 g
(0.01 mol) of compound I and 1.51 g (0.01 mol) of
4-nitrobenzaldehyde in 25 ml of ethanol containing
one drop of glacial acetic acid was heated for 5 h under
reflux. The mixture was cooled, and the precipitate
was filtered off, dried in air, and recrystallized from
ethanol–dioxane (5:1). Yield 2.85 g (76%), yellow
crystals, mp 159–160°C. IR spectrum, ν, cm–1: 3310
(NH), 1710 (C=O), 1645 (C=N), 1610, 1595, 1575
1
(C=Carom), 1517 (νasNO2), 1345 (νsNO2). H NMR
spectrum (DMSO-d6), δ, ppm: 5.16 s (2H, CH2Ph),
7.32–7.51 m (9H, Harom), 8.18 d (2H, Harom, J =
8.0 Hz), 8.35 d (2H, Harom, J = 8.0 Hz), 8.82 s (1H,
N=CH), 9.92 br.s (1H, NH). Mass spectrum, m/z
(Irel, %): 376 (7) [M + 1]+, 375 (16) [M]+, 331 (6), 267
(5), 240 (55), 194 (26), 91 (97), 77 (17). Found, %:
C 67.01; H 4.55; N 11.06. C21H17N3O4. Calculated, %:
C 67.20; H 4.53; N 11.20. M 375.40.
Benzyl {4-[2-(4-nitrophenyl)-4-oxo-1,3-thiazoli-
din-3-yl]phenyl}carbamate (XI). A mixture of 1.88 g
(5 mmol) of compound VII and 0.71 ml (0.01 mol) of
sulfanylacetic acid in 12 ml of anhydrous dimethyl-
formamide was heated for 12 h at 120°C. The mixture
was cooled to room temperature and poured into 50 ml
of 10% aqueous sodium hydrogen carbonate, and the
precipitate was filtered off, washed with water (20 ml)
on a filter, dried in air, and recrystallized from ethanol.
Yield 1.46 g (65%), dark yellow crystals, mp 105–
106°C. IR spectrum, ν, cm–1: 3330 (NH), 1710, 1780
(C=O), 1610, 1585, 1570 (C=Carom), 1517 (νasNO2),
Compounds VIII and IX were synthesized in
a similar way.
Benzyl {4-[(2,4-dihydroxyphenyl)methylidene]-
aminophenyl}carbamate (VIII) was synthesized
from 2.42 g (0.01 mol) of compound I and 1.38 g
(0.01 mol) of 2,4-dihydroxybenzaldehyde. Yield 3.08 g
(85%), yellow crystals, mp 152–153°C (from EtOH–
dioxane, 5:1 by volume). IR spectrum, ν, cm–1: 3310
(NH), 1710 (C=O), 1650 (C=N), 1610, 1595, 1575
(C=Carom). Found, %: C 69.71; H 4.84; N 7.58.
C21H18N2O4. Calculated, %: C 69.61; H 4.97; N 7.74.
1
1345 (νsNO2), 687 (C–S–C). H NMR spectrum
(DMSO-d6), δ, ppm: 4.15 s (2H, CH2), 5.21 s (2H,
CH2Ph), 5.32 s (1H, 2-H), 7.22–7.29 m (7H, Harom),
7.40 d (1H, Harom, J = 9.0 Hz), 7.48 d (1H, Harom, J =
9.0 Hz), 7.56 d (2H, Harom, J = 8.7 Hz), 7.90 d (2H,
Cyclohexyl {4-[(4-methoxyphenyl)methylidene]-
aminophenyl}carbamate (IX) was synthesized from
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SOME CHEMICAL TRANSFORMATIONS OF ALKYL (4-AMINOPHENYL)CARBAMATES
1009
9. Structure Determination of Organic Compounds: Tables
of Spectral Data, Pretsch, E., Bühlmann, P., and
Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed.
10. Kelley, J.L., Koble, C.S., Davis, R.G., McLean, M.S.,
Soroko, F.E.B., and Cooper, R., J. Med. Chem., 1995,
vol. 38, p. 4131.
H
arom, J = 9.0 Hz), 9.62 br.s (1H, NH). Found, %:
C 61.29; H 4.11; N 9.40. C23H19N3O5S. Calculated, %:
C 61.47; H 4.23; N 9.35.
REFERENCES
11. Mosti, L., Menozzi, G., Schenone, P., Gaion, R.M., and
Belluco, P., Farmaco, 1992, vol. 47, p. 427.
12. Adsule, S., Barve, V., Chen, D., Ahmed, F., Dou, Q.P.,
1. Pattan, S.R., Rasal, V.P., Venkatramana, N.V., Khade, B.,
Butle, S.R., Jadhav, S.G., Desai, B.G., and Manvi, F.V.,
Indian J. Chem., Sect. B, 2007, vol. 46, p. 698.
and Padhye, S., J. Med. Chem., 2006, vol. 49, p. 7242.
2. Sutariya, B., Raziya, S.K., Mohan, S., and Samba-
siva, S.V., Indian J. Chem., Sect. B, 2007, vol. 46, p. 884.
13. Hojo, M., Tanaka, Y., Katayama, O., and Teramoto, N.,
Arzneim. Forsch., 1993, vol. 43, p. 847.
14. Swiatek, P. and Malinka, W., Acta Polon. Pharm., 2004,
3. Barral, K., Moorhouse, A.D., and Moses, J.E., Org.
Lett., 2007, vol. 9, p. 1809.
vol. 61, p. 98.
4. Jacob, J. and Jones, W.D., J. Org. Chem., 2003, vol. 68,
p. 3568.
15. Vibhute, A.Y., Junne, S.B., Gurav, V.M., and
Vibhute, Y.B., J. Chem. Pharm. Res., 2010, vol. 2,
p. 300.
5. Velikorodov, A.V., Russ. J. Org. Chem., 2000, vol. 36,
p. 233.
16. Junne, S.B., Kadam, A.B., Zangade, S.B., Shinde, S.L.,
and Vibhute, Y.B., Int. Multidiscip. Res. J., 2012, vol. 2,
no. 6, p. 44.
17. Sayyed, M.A., Nalwar, Y.S., Mokle, S.S., Vibhute, A.Y.,
Khansole, S.V., and Vibhute, Y.B., Int. J. Chem. Tech.
Res., 2009, vol. 1, p. 606.
6. Trusova, M.E., Cand. Sci. (Chem.) Dissertation, Tomsk,
2009.
7. Filimonov, V.D., Trusova, M., Postnikov, P., Krasnokut-
skaya, E.A., Lee, Y.M., Hwang, H.Y., and Chi, Ki-W.,
Org. Lett., 2008, vol. 10, p. 3961.
8. Zeller, K.-P., The Chemistry of Triple-Bonded Func-
tional Groups, Patai, S. and Rappoport, Z., Chichester:
Wiley, 1983, part 1, p. 57.
18. Shreenivas, M.T., Chetan, B.P., and Bhat, A.R.,
J. Pharm. Sci. Technol., 2009, vol. 1, p. 88.
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