Synthesis of 2-substituted aminothiazol-4(5H)-ones proceeding from carboxylactones

Article abstract of DOI:10.1134/S1070428011080148

New representatives of 2,2,4-trisubstituted butano-4-lactones were synthesized. By a series of transformations the corresponding γ-carboxylactones were obtained. The latter served as starting compounds for preparation of heteryl-linked lactones, 5-[5-{(al

Full text of DOI:10.1134/S1070428011080148

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 8, pp. 1204−1208. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © T.V. Kochikyan, M.A. Samvelyan, V. S. Arutyunyan, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 8, pp. 1186−1190.
Synthesis of 2-Substituted Aminothiazol-4(5H)-ones
Proceeding from Carboxylactones
T. V. Kochikyan, M. A. Samvelyan, and V. S. Arutyunyan
Yerevan State University, Yerevan, 375025 Armenia
е-mail: melan29@rambler.ru
Received October 27, 2010
Abstract—New representatives of 2,2,4-trisubstituted butano-4-lactones were synthesized. By a series of
transformations the corresponding γ-carboxylactones were obtained. The latter served as starting compounds for
preparation of heteryl-linked lactones, 5-[5-{(alkoxymethyl)-2-oxotetrahydrofuran-3-yl}methyl]-2-arylamino-
thiazol-4(5Н)-ones.
DOI: 10.1134/S1070428011080148
Carboxylactones are known to be successfully used
in the synthesis of compounds of various classes. In par-
ticular, some carboxylactone esters are used as additives
to rocket propellants [1], in the synthesis of oxazolines
[2], prostaglandins derivatives [3], and triazolyllactones
[4–8] exhibiting hypotensive and antitumor action.
IIc which by the alkaline hydrolysis were converted
into 3-[5-(alkoxymethyl)-2-oxotetrahydrofuran-3-yl]-
propionic acids IIIа–IIIc (Scheme 1).
The best results were obtained in the condensation
catalyzed with sodium methylate followed by the hydro-
lysis with 30% solution of NaOH.
The aim of this study was the extension of the
choice of carboxylactones, the development of the
procedures for the preparation therefrom of new hetero-
cyclic compounds, and the investigation of the useful
practical properties of the latter. To fulfill this goal we
selected as initial compounds ethyl 5-alkoxymethyl-
2-oxotetrahydrofuran-3-carboxylates Iа–Ic, being
good CH-acids. We carried out the condensation of
compounds Iа–Ic with methyl acrylate in the condi-
tions of Michael reaction. As a result we obtained in
high yields ethyl 5-(alkoxymethyl)-3-(3-methoxy-3-
oxopropyl)-2-oxotetrahydrofuran-3-carboxylates IIа–
Taking into consideration that the halo-substituted
γ-lactones are successfully used for preparation of com-
pounds of various classes [9, 10], analogs of natural
substances [11, 12], carboxylactones IIIа–IIIc were
converted into the corresponding acyl chlorides IVа–IVc
by the treatment with thionyl chloride in the presence
of catalytic quantity of DMF (Scheme 2). Further the
bromination of compounds IVа–IVc and the subse-
quent reaction of the obtained chlorides of α-bromoacids
with anhydrous ethanol afforded in a high yield ethyl
2-bromo-3-(5-alkoxymethyl 2-oxotetrahydrofuran-3-yl)
propanoates Vа–Vc (Scheme 2).
Scheme 1.
COOEt
CH2CH2COOCH3
_
COOEt
(1) OH
CH2CH2COOH
O
(2) H+, _CO2
CH2=CHCOOCH3
ROH2C
ROH2C
ROH2C
CH3ONa
O
O
O
O
O
Ia_Ic
IIa_IIc
IIIa_IIIc
R = C2H5 (a), iso-C3H7 (b), C5H11 (c).
1204

SYNTHESIS OF 2-SUBSTITUTED AMINOTHIAZOL-4(5H)-ONES
1205
Scheme 2.
O
O
CH2CH2C
O
CH2CH2C
O
Cl
OH
SOCl2
DMF
ROH2C
ROH2C
O
O
IVa_IVc
O
O
CH2CHC
CH2CHC
Br2
C2H5OH
OC2H5
Cl
Br
O
Br
O
ROH2C
ROH2C
CCl4
O
O
Va_Vc
R = C2H5 (a), iso-C3H7 (b), C5H11 (c).
1H NMR data in the case of electron-donor substituents
the ratio (VI):(VII) is 90 : 10, and in the case of electron-
acceptor substituents, 60 : 40.
The bromination is favorably performed in anhydrous
CCl4 at 60–65°С.
In order to obtain new heteryl-linked γ-lactones
we studied the reaction of compounds Vа–Vc with
arylthioureas. As a result of the substitution followed
by heterocyclization we obtained in good yields hydro-
bromides of 2-arylamino derivatives of thiazol-4(5Н)-
ones whose treating with aqueous ammonia gave the
corresponding free bases VIа–VIh (Scheme 3).
EXPERIMENTAL
1H NMR spectra were registered on a spectrometer
Varian Mercury-300 (300 MHz), solvent CDCl3, internal
reference TMS. IR spectra were recorded on a spectropho-
tometer Nicolet FTIR Nexus from liquid films or mulls
in mineral oil. TLC was carried out on Silufol UV-254
plates, eluents ethanol–benzene–hexane, 3 : 3 : 10 v/v
(А), ethanol–benzene, 1 : 5 v/v (B); development in io-
dine vapor. Melting points were measured on a Boёtius
heating block.
The analysis of the spectral characteristics of the reac-
tion products showed that in the solution aryl-substituted
derivatives VI exist in a tautomeric equilibrium with
imine form VII (Scheme 4).
The electronic character of substituent R' in the aro-
matic ring affects the ratio of the tautomers.According to
Scheme 3.
O
O
N
CH2
CH2
O
NH2C(S)NHR'
NH4OH
Va_Vc
N
ROH2C
ROH2C
S
S
O
O
O
_
.
NHR'
NH R'
HBr
VIa_VIh
R = C2H5, R' = p-CH3C6H4 (a), p-C2H5OC6H4 (b); R = iso-C3H7, R' = p-CH3C6H4 (c), p-C2H5OC6H4 (d), C6H5 (e); R =
C5H11, R' = p-CH3C6H4 (f), p-C2H5OC6H4 (g), C6H5 (h).
Scheme 4.
O
O
N
CH2
O
CH2
O
NH
ROH2C
S
ROH2C
S
O
O
HN
N
R'
R'
VI
VII
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 8 2011

KOCHIKYAN et al.
1206
3-[5-(Isopropoxymethyl)-2-oxotetrahydrofuran-
Initial ethyl 5-(alkoxymethyl)-2-oxotetrahydrofuran-
3-yl]propionic acid (IIIb). Yield 76%, bp 159°C (1 mm
Hg), nD20 1.4667, d420 1.1300. Found, %: С 57.50; Н 7.69.
С11Н18О5. Calculated, %: С 57.39; Н 7.83.
3-carboxylates Iа–Ic were prepared by method [13].
Ethyl 5-(alkoxymethyl)-3-(3-methoxy-3-
oxopropyl)-2-oxotetrahydrofuran-3-carboxylates
IIа–IIc. General procedure. A mixture of 0.1 mol
of ethyl 5-(alkoxymethyl)-2-oxotetrahydrofuran-3-
carboxylate Ia–Ic and 0.105 mol of methyl acrylate
was heated to 45°C, and a solution of sodium methylate
obtained by dissolving 0.2 g of metallic sodium in 20 ml
of anhydrous methanol was added dropwise maintaining
the temperature at 45–50°C. The mixture was stirred for
4 h at 20–25°C, then it was acidified by dilute hydro-
chloric acid to рН 2–3. The product was extracted into
ethyl ether, the extract was washed with water, dried with
MgSO4, the solvent was distilled off, and the residue was
purified by distillation.
3-[5-(Pentoxymethyl)-2-oxotetrahydrofuran-3-yl]
propionic acid (IIIc). Yield 83%, bp 192–193°C (1 mm
Hg), nD20 1.4670, d420 1.0981. Found, %: С 60.35; Н 8.65.
С13Н22О5. Calculated, %: С 60.47; Н 8.53.
3-[5-(Alkoxymethyl)-2-oxotetrahydrofuran-3-yl]
propionyl chlorides IVа–IVc. General procedure.
A mixture of 0.05 mol of compound IIIа–IIIc in 55 ml
of anhydrous benzene, 0.5 ml of DMF, and 0.055 mol of
thionyl chloride was kept at room temperature for 1 h,
then it was boiled for 4 h. The solvent was removed in
a vacuum, the residue was purified by distillation
3-[5-(Ethoxymethyl)-2-oxotetrahydrofuran-3-
yl]propionyl chloride (IVа). Yield 76%, bp 165°C
(3 mm Hg), nD20 1.4670, d420 1.1778. Found, %: С 51.17;
Н 6.65; Cl 15.50. С10Н15О4Cl. Calculated, %: С 51.17;
Н 6.39; Cl 15.14.
Ethyl 5-(ethoxymethyl)-3-(3-methoxy-3-
oxopropyl)-2-oxotetrahydrofuran-3-carboxylate
(IIа). Yield 82%, bp 159°C (2 mm Hg), Rf 0.47 (A),
nD20 1.4585, d420 1.1664. Found, %: С 55.40; Н 7.00.
С14Н22О7. Calculated, %: С 55.63; Н 7.28.
3-[5-(Isopropoxymethyl)-2-oxotetrahydrofuran-
3-yl]propionyl chloride (IVb). Yield 70%, bp 156°C
(1 mm Hg), nD20 1.4660, d420 1.1463. Found, %: С 53.00;
Н 6.90; Cl 14.70. С11Н17О4Cl. Calculated, %: С 53.12;
Н 6.84; Cl 14.29.
Ethyl 5-(isopropoxymethyl)-3-(3-methoxy-3-
oxopropyl)-2-oxotetrahydrofuran-3-carboxylate (IIb).
Yield 88%, bp 165–166°C (2 mm Hg), Rf 0.49 (A), nD20
1.4578, d420 1.1430. Found, %: С 57.00; Н 7.69. С15Н24О7.
Calculated, %: С 56.96; Н 7.59.
3-[5-(Pentoxymethyl)-2-oxotetrahydrofuran-3-yl]
propionyl chloride (IVc). Yield 78%, bp 173°C (1 mm
Hg), nD20 1.4640, d420 1.1055. Found, %: С 56.30; Н 7.70;
Cl 13.00. С13Н21О4Cl. Calculated, %: С 56.42; Н 7.59;
Cl 12.84.
Ethyl 5-(pentoxymethyl)-3-(3-methoxy-3-
oxopropyl)-2-oxotetrahydrofuran-3-carboxylate
(IIc). Yield 89%, bp 170–171°C (1 mm Hg), Rf 0.50
(A), nD20 1.4572, d420 1.0967. Found, %: С 59.00; Н 8.40.
С17Н28О7. Calculated, %: С 59.30; Н 8.14.
Ethyl 2-bromo-3-[5-(alkoxymethyl)-2-oxo-
tetrahydrofuran-3-yl]propionate Vа–Vc. General
procedure. A solution of 0.036 mol of compound IVа–
IVc in 30 ml of anhydrous CCl4 was heated at 60°C,
and to it was added dropwise a solution of 0.036 mol of
bromine in 10 ml of CCl4. After the addition of all bro-
mine the mixture was boiled for 2 h, cooled, and 20 ml of
anhydrous ethanol was added, the mixture was boiled for
3 h, the solvent was removed, the residue was distilled.
3-[5-(Alkoxymethyl)-2-oxotetrahydrofuran-3-yl]
propionic acids IIIа–IIIc. General procedure. To a
mixture of 11.2 g (0.28 mol) of 30% solution of sodium
hydroxide and 0.8 ml of catamine AB at room tempera-
ture was slowly added 0.08 mol of compound IIа–IIc,
the mixture was stirred for 2 h, and then for 4 h more
at 65–70°C. The mixture was cooled and acidified with
concn. HCl till рН 1–2. The product was extracted into
ethyl ether, the extract was washed with water, dried
with MgSO4, the solvent was distilled off, the residue
was subjected to decarboxylation at 250–300°C at the
pressure of 15–20 mm Hg within 30 min, and the product
was distilled.
IR spectra of compounds Vа–Vc, ν, cm–1: 1770
(С=Olactone), 1735 (С=Oester), 1125, 1180, 1280 (С–О–С),
680 (С–Br).
Ethyl 2-bromo-3-[5-(ethoxymethyl)-2-
oxotetrahydrofuran-3-yl]propionate (Vа). Yield 73%,
bp 172–175°C (1 mm Hg), Rf 0.53 (A), nD20 1.4695,
d420 1.1764. Found, %: С 44.40; Н 6.00; Br 25.00.
С12Н19О5Br. Calculated, %: С 44.58; Н 5.88; Br 24.77.
3-[5-(Ethoxymethyl)-2-oxotetrahydrofuran-3-yl]
propionic acid (IIIа). Yield 77%, bp 176°C (1 mm Hg),
nD20 1.4695, d420 1.1740. Found, %: С 55.00; Н 7.69.
С10Н16О5. Calculated, %: С 55.56; Н 7.401.
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SYNTHESIS OF 2-SUBSTITUTED AMINOTHIAZOL-4(5H)-ONES
1207
Ethyl 2-bromo-3-[5-(isopropoxymethyl)-2-
oxotetrahydrofuran-3-yl]propionate (Vb). Yield 65%,
bp 174°C (1 mm Hg), Rf 0.55 (A), n 20 1.4675, d420 1.1300.
Found, %: С 46.50; Н 6.00; BrD24.00. С13Н21О5Br.
Calculated, %: С 46.29; Н 6.23; Br 23.74.
J 8.7 Hz), 6.91–7.01 m (1Нarom), 7.62 d (1Нarom, J 8.7 Hz),
10.81 d (1Н, NH, J 6.3 Hz). Found, %: С 59.00; Н 6.20;
N 7.54; S 8.02. С19Н24N2О5S. Calculated, %: С 58.15;
Н 6.16; N 7.14; S 8.18.
5-{5-[(Isopropoxymethyl)-2-oxotetrahydrofuran-
3-yl]methyl}-2-p-tolylaminothiazol-4(5Н)-one (VIc).
Yield 70%, mp 128–129°C (water–ethanol, 1 : 2), Rf 0.58
(B). IR spectrum, ν, cm–1: 3300, 3180 (NH), 3050 (=СН),
1765 (С=Olactone), 1675 (С=Ocyclic amide), 1610 (С=Сarom),
1565 (С= N), 1190, 1110 (С–О–С). 1Н NMR spectrum,
δ, ppm: 1.00–1.28 m [6H, (CH3)2CH], 1.99–2.29 m (4H,
CHCH2CHCH2), 2.32 s (3H, CH3-Ar), 3.37–3.72 m (3Н,
СНОСН2), 3.99–5.15 m (2Н, СН in furanone), 6.94 d
(1Н, СН in thiazolidone, J 7.1 Hz), 7.04–7.16 m (2Нarom),
7.27 d (2Нarom, J 8.7 Hz), 10.85 d, 11.60 br.s (1Н, NH,
J 4.8 Hz). Found, %: С 60.80; Н 6.50; N 7.50; S 8.00.
С19Н24N2О4S. Calculated, %: С 60.64; Н 6.38; N 7.45;
S 8.51.
Ethyl 2-bromo-3-[5-(pentoxymethyl)-2-
oxotetrahydrofuran-3-yl]propionate (Vc). Yield 70%,
bp 178°C (1 mm Hg), Rf 0.46 (A), n 20 1.4685, d420 1.1420.
Found, %: С 49.50; Н 6.80; BrD22.00. С15Н25О5Br.
Calculated, %: С 49.31; Н 6.85; Br 21.92.
5-{5-[(Alkoxymethyl)-2-oxotetrahydrofuran-3-yl]
methyl}-2-arylaminothiazol-4(5Н)-ones VIа–VIh.
General procedure. To a mixture of 0.006 mol of thio-
urea derivative in 5 ml of anhydrous acetone was added
dropwise a solution of 0.006 mol of compound Vа–Vc
in 5 ml of acetone, the mixture was stirred for 1 h at
room temperature and was boiled for 1 h. On removing
acetone water was added, and next aqueous ammonia was
added till рН 7, the precipitate was separated, dried, and
recrystallized from aqueous ethanol.
5-{5-[(Isopropoxymethyl)-2-oxotetrahydro-
furan-3-yl]methyl}-2-p-ethoxyphenylamino-
thiazol-4(5Н)-one (VId). Yield 80%, mp 130–131°C
(water–ethanol, 1 : 2), Rf 0.60 (B). IR spectrum, ν,
cm–1: 3250, 3190 (NH), 3050 (=СН), 1755 (С=Olactone),
1670 (С=Ocyclic amide), 1610 (С=Сarom), 1555 (С=N),
5-{5-[(Ethoxymethyl)-2-oxotetrahydrofuran-3-
yl]methyl}-2-p-tolylaminothiazol-4(5Н)-one (VIа).
Yield 65%, mp 98–100°C (water–ethanol, 3 : 2),
Rf 0.55 (B). IR spectrum, ν, cm–1: 3250, 3190 (NH),
3080 (=СН), 1755 (С=Olactone), 1675 (С=Ocyclic amide),
1610 (С=Сarom), 1560 (С=N), 1180, 1120 (С–О–С).
1Н NMR spectrum, δ, ppm: 1.11–1.29 m (3H, CH3CH2),
1.59–2.33 m (4H, CHCH2CHCH2), 2.33 s (3H, CH3-Ar),
3.40–3.66 m (4H, CH2OCH2), 4.02–4.14 m, 4.21 t.t,
4.44–4.54 m (1Н, СН in furanone, J 10.3, J 4.8 Hz),
4.34–4.44 m, 4.55–4.68 m (1Н, СНО in furanone),
6.89 d.d (1Н, СН в thiazolidоне, J 8.3, J 3.6 Hz), 7.10,
7.27, 7.61 d (1Нarom, J 7.9, J 8.7, J 7.9 Hz), 10.86 s
and 11.58 br.s (1Н, NH). Found, %: С 59.12; Н 6.00;
N 8.00; S 8.50. С18Н22N2О4S. Calculated, %: С 59.67;
Н 6.12; N 7.73; S 8.85.
1
1180, 1120 (С–О–С). Н NMR spectrum, δ, ppm:
0.70–1.35 m [6H, (CH3)2CH], 1.40 t (3Н, СН3СН2О-Ar,
J 6.7 Hz), 1.54–2.47 m (4H, CHCH2CHCH2), 2.57 and
3.38–3.71 m (3H, CHOCH2), 4.01 q (2Н, СН3СН2О,
J 6.9 Hz), 4.10–5.23 m (2Н, СН in furanone), 6.80 m
(1Н, СН in thiazolidone), 6.82 d (2Нarom, J 8.7 Hz),
6.89–7.08 m (1Нarom), 7.63 d (1Нarom, J 8.7 Hz), 10.80 and
11.53 br.s (1Н, NH). Found, %: С 59.00; Н 6.30; N 7.00;
S 7.50. С20Н26N2О5S. Calculated, %: С 59.11; Н 6.40;
N 6.89; S 7.90.
5-{5-[(Isopropoxymethyl)-2-oxotetrahydrofuran-
3-yl]methyl}-2-phenylthiazol-4(5Н)-one (VIe). Yield
75%, mp 140–141°C (water–ethanol, 1 : 2), Rf 0.54
(B). IR spectrum, ν, cm–1: 3250, 3190 (NH), 3080
(=СН), 1755 (С=Olactone), 1675 (С=Ocyclic amide), 1610
(С=Сarom), 1560 (С=N), 1180, 1120 (С–О–С). 1Н NMR
spectrum, δ, ppm: 0.99–1.25 m [6H, (CH3)2CH],
2.00–2.31 m (4H, CHCH2CHCH2), 3.37–3.72 m (3Н,
СНОСН2), 3.99–5.15 m (2Н, СН in furanone), 6.57 t.t
(1Hп, J 7.2, J 1.1 Hz), 6.66 m (2Но), 7.09 m (2Нm),
6.94 d (1Н, СН in thiazolidone, J 7.1 Hz), 10.80 d,
11.56 br.s (1Н, NH, J 4.8 Hz). Found, %: С 59.25; Н 6.25;
N 7.80; S 8.50. С18Н22N2О4S. Calculated, %: С 59.67;
Н 6.08; N 7.73; S 8.84.
5-{5-[(Ethoxymethyl)-2-oxotetrahydrofuran-3-yl]
methyl}-2-p-ethoxyphenylaminothiazol-4(5Н)-one
(VIb). Yield 80%, mp 142–143°C (water–ethanol, 1 :
2), Rf 0.57 (B). IR spectrum, ν, cm–1: 3250, 3190 (NH),
3080 (=СН), 1755 (С=Olactone), 1670 (С=Ocyclic amide),
1605 (С=Сarom), 1550 (С=N), 1200, 1140 (С–О–С).
1Н NMR spectrum, δ, ppm: 1.07–1.28 m (3H, CH3CH2),
1.40 t (3Н, СН3СН2О-Ar, J 6.07 Hz), 1.60–2.47 m (4H,
CHCH2CHCH2), 3.44–3.63 m (4H, CH2OCH2), 4.01 q
(2Н, СН3СН2О-Ar, J 7.1 Hz), 4.14–4.44 m (1Н, СН in
furanone), 4.44–4.68 m (1Н, СНО in furanone), 6.88 d.d
(1Н, СН in thiazolidone, J 8.3, J 3.6 Hz), 6.82 d (2Нarom
,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 8 2011

KOCHIKYAN et al.
1208
5-{5-[(Pentoxymethyl)-2-oxotetrahydrofuran-3-yl]
δ, ppm: 0.98–1.02 m (3H, CH3), 1.18–1.49 m (6H, CH2),
2.01–2.33 m (4H, CHCH2CHCH2), 3.38–3.77 m (4Н,
СН2ОСН2), 3.95–5.16 m (2Н, СН in furanone), 6.58 t.t
(1Hp, J 7.2, J 1.1 Hz), 6.68 m (2Нo), 7.10 m (2Нm), 6.91 d
(1Н, СН in thiazolidone, J 7.1 Hz), 10.76 d, 11.52 br.s
(1Н, NH, J 4.8 Hz). Found, %: С 60.90; Н 6.80; N 7.68;
S 8.90. С20Н26N2О5S. Calculated, %: С 61.54; Н 6.71;
N 7.18; S 8.20.
methyl}-2-p-tolylaminothiazol-4(5Н)-one (VIf).. Yield
70%, mp 112–113°C (water–ethanol, 1 : 2), Rf 0.65 (B).
IR spectrum, ν, cm–1: 3250, 3190 (NH), 3080 (=СН),
1755 (С=Olactone), 1675 (С=Ocyclic amide), 1610 (С=Сarom),
1
1560 (С=N), 1180, 1120 (С–О–С). Н NMR spectrum,
δ, ppm: 1.01–1.09 m (3H, CH3), 1.20–1.53 m (6H, CH2),
1.61–2.38 m (4H, CHCH2CHCH2), 2.34 s (3H, CH3-Ar),
3.42–3.68 m (4H, CH2OCH2), 4.05–4.16 m, 4.22 t.t,
4.45–4.56 m (1Н, СН in furanone, J 10.3, J 4.8 Hz),
4.34–4.44 m, 4.55–4.68 m (1Н, СНО in furanone),
6.89 d.d (1Н, СН in thiazolidone, J 8.3, J 3.6 Hz), 7.10,
7.27, 7.61 d (1Нarom, J 7.9, J 8.7, J 7.9 Hz), 10.89 s and
11.53 br.s (1Н, NH). Found, %: С 62.25; Н 7.00; N 7.10;
S 8.10. С21Н28N2О4S. Calculated, %: С 62.35; Н 6.98;
N 6.93; S 7.93.
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5-{5-[(Pentoxymethyl)-2-oxotetrahydrofuran-3-yl]
methyl}-2-p-ethoxyphenylaminothiazol-4(5Н)-one
(VIg). Yield 70%, mp 173–174°C (water–ethanol, 1 : 4),
Rf 0.54 (B). IR spectrum, ν, cm–1: 3250, 3190 (NH), 3080
(=СН), 1755 (С=Olactone), 1675 (С=Ocyclic amide), 1610
1
(С=Сarom), 1560 (С= N), 1180, 1120 (С–О–С). Н NMR
spectrum, δ, ppm: 1.01–1.09 m (3H, CH3), 1.20–1.53 m
(6H, CH2), 1.42 t (3Н, СН3СН2О, J 6.07 Hz), 1.60–2.47 m
(4H, CHCH2CHCH2), 3.44–3.63 m (4H, CH2OCH2),
4.02 q (2Н, Н3СН2О, J 7.1 Hz), 4.13–4.42 m (1Н, СН in
furanone), 4.46–4.71 m (1Н, СНО in furanone), 6.89 d.d
(1Н, СН in thiazolidone, J 8.3, J 3.6 Hz), 6.81 d (2Нarom
,
J 8.7 Hz), 6.92–7.05 m (1Нarom), 7.63 d (1Нarom, J 8.7 Hz),
10.78 d (1Н, NH, J 6.3 Hz). Found, %: С 59.60; Н 6.80;
N 6.75; S 7.70. С22Н30N2О5S. Calculated, %: С 60.00;
Н 6.91; N 6.36; S 7.27.
10. Zebic, V., Skaric, V., Ruzic-Toros, Z., Kojic-Prodic, B.
Croat. Chem. Acta., 1986, vol. 59, p. 491.
5-{5-[(Pentoxymethyl)-2-oxotetrahydrofuran-3-yl]
methyl}-2-phenylaminothiazol-4(5Н)-one (VIh). Yield
75%, mp 129–130°C (water–ethanol, 1:2), Rf 0.48 (B).
IR spectrum, ν, cm–1: 3250, 3190 (NH), 3080 (=СН),
1755 (С=Olactone), 1675 (С=Ocyclic amide), 1610 (С=Сarom),
11. Avchibasi, H., Anil, H., and Torpak, M., Fitochem., 1987,
vol. 26, p. 2852.
12. Itakava, H., Morita, H., Osawa, K., Watanabe, K., and
Itaka, Y., Chem. Pharm. Bull., 1987, vol. 35, p. 2849.
13. Arutyunyan, V.S., Kochikyan, T.V., Egiazaryan, N.S., and
Avetisyan, A.A., Khim. Zh. Arm., 1994, vol. 47, p. 91.
1
1560 (С=N), 1180, 1120 (С–О–С). Н NMR spectrum,
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