Synthesis of enamino ketones from N-(2-vinyloxyalkyl)-ethane-1,2-diamines

Article abstract of DOI:10.1134/S1070428010040068

Reactions of N-(2-vinyloxyalkyl)ethane-1,2-diamines with 1,3-dicarbonyl compounds gave the corresponding enamino ketones in almost quantitative yield (98-99%).

Full text of DOI:10.1134/S1070428010040068

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2010, Vol. 46, No. 4, pp. 491–494. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © B.F. Kukharev, V.K. Stankevich, N.A. Lobanova, G.R. Klimenko, V.V. Stankevich, E.V. Bragin, 2010, published in Zhurnal
Organicheskoi Khimii, 2010, Vol. 46, No. 4, pp. 501–504.
Synthesis of Enamino Ketones from N-(2-Vinyloxyalkyl)-
ethane-1,2-diamines
B. F. Kukharev, V. K. Stankevich, N. A. Lobanova, G. R. Klimenko,
V. V. Stankevich, and E. V. Bragin
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: irk_inst_chem@irioch.irk.ru
Received June 24, 2009
Abstract—Reactions of N-(2-vinyloxyalkyl)ethane-1,2-diamines with 1,3-dicarbonyl compounds gave the
corresponding enamino ketones in almost quantitative yield (98–99%).
DOI: 10.1134/S1070428010040068
Enaminones are universal and readily accessible
synthons for a wide series of heterocyclic compounds;
in addition, they exhibit biological activity [1–3]. The
reactivity and biological activity of enaminones
strongly depend on the nature of the amine fragment.
In the present work we were the first to use
N-(2-vinyloxyalkyl)ethane-1,2-diamines as amine
component for the synthesis of enamino ketones.
N-(2-Vinyloxyalkyl)ethane-1,2-diamines themselves
possess broad synthetic potential and diverse biologi-
cal activity [4], and we anticipated enhancement of
these properties in the resulting enaminones.
IIa, IIb, and III were performed by heating equimolar
mixtures of the reactants in boiling benzene with
simultaneous removal of liberated water as azeotrope
(Scheme 1). All enaminones IVa–IVf and Va–Vc were
obtained in almost quantitative yield. Enaminones
IVa–IVf derived from acetylacetone (IIa) and ethyl
acetoacetate (IIb) are viscous oily substances which
decompose upon distillation (at a residual pressure of
1–2 mm) but are stable on prolonged storage at room
temperature under nitrogen. Enaminones Va–Vc
derived from 5,5-dimethylcyclohexane-1,3-dione are
crystalline substances with sharp melting points.
The condensation of N-(2-vinyloxyalkyl)ethane-
1,2-diamines Ia–Ic with 1,3-dicarbonyl compounds
In the IR spectra of compounds IVa–IVf and Va–
Vc we observed absorption bands in the regions 1500–
Scheme 1.
Me
R
MeC(O)CH2C(O)R (IIa, IIb)
X
N
O
·
·
·
H
O
N
H2C
H
IVa–IVf
X
NH2
O
O
N
H2C
Me
Me
H
O
(III)
Ia–Ic
Me
O
Me
X
NH
O
N
H
H2C
Va–Vc
I, V, X = CH2CH2 (a), CH2CH(OH)CH2 (b), CH2CH2OCH2CH(OH)CH2 (c); II, R = Me (a), OEt (b); IV, X = CH2CH2, R = Me (a),
OEt (e); X = CH2CH(OH)CH2, R = Me (b), OEt (d); X = CH2CH2OCH2CH(OH)CH2, R = Me (c), OEt (f).
491

KUKHAREV et al.
492
1585 and 1600–1675 cm–1, which correspond to
stretching vibrations of the N–C=CH–C=O conjugated
bond system; these bands completely overlap those
belonging to stretching vibrations of the vinyloxy
group (1605–1615 cm–1); stretching vibrations of the
=C–H bonds appeared in the region 3033–3117 cm–1.
the procedure described in [5], and N-(2-vinyloxy-
alkyl)ethane-1,2-diamines Ib and Ic were prepared as
reported in [6] from ethane-1,2-diamine and vinyl or
2-vinyloxyethyl glycidyl ether.
Enamino ketones IVa–IVf and Va–Vc (general
procedure). A mixture of 0.02 mol of N-(2-vinyloxy-
alkyl)ethane-1,2-diamine Ia–Ic, 0.02 mol of diketone
IIa, IIb, or III in 100 ml of benzene was heated under
reflux in a flask equipped with a Dean–Stark trap until
water no longer separated. The solvent was distilled
off, and the oily residue was dried at room temperature
under reduced pressure (1–2 mm) until constant
weight. Some products (dimedone derivatives Va–Vc)
crystallized.
1
The H NMR spectra of IVa–IVf and Va–Vc con-
tained only one signal from the olefinic proton in the
NC=CHC=O fragment at δ 4.44–4.91 (IVa–IVf) and
5.07–5.08 ppm (Va–Vc), indicating formation of only
one isomer with respect to the double C=C bond.
Compounds IVa–IVf displayed in the 1H NMR spectra
a broadened signal from the C=CNH proton involved
in intramolecular hydrogen bond (H-chelate ring) at
δ 10.81–10.93 (IVa–IVc) or 8.62–8.79 ppm (IVd–
IVf). In the spectra of dimedone derivatives Va–Vc the
corresponding signal was located in a stronger field, at
δ 5.14–5.27 ppm, for fixed trans-configuration of the
double C=C bond makes intramolecular hydrogen
bonding NH···O=C impossible. The above data are
fully consistent with the chemical shifts of protons in
structurally related enamino ketones obtained from
1,3-dicarbonyl compounds and other primary amines
[3]. The signal from proton on the nitrogen atom in the
C=CNHCH2 group of enaminones IVa–IVf and Va–
Vc is slightly broadened, and its intensity corresponds
to one proton. Protons in the neighboring methylene
group give rise to a multiplet (unresolved doublet of
triplets) which looks like a quartet with a coupling
constant J of 5.8–6.2 Hz. The intensity of the
C=CNHCH2 signal indicates the lack of proton
exchange with the NH and OH groups under the given
conditions.
(E)-4-[2-(2-Vinyloxyethylamino)ethylamino]-
pent-3-en-2-one (IVa). Yield 98%, nD20 = 1.5248. IR
spectrum, ν, cm–1: 3285, 3105, 3065, 3030, 2915,
2860, 2825, 1620, 1600, 1555, 1500, 1425, 1360,
1340, 1300, 1280, 1180, 1120, 1060, 1000, 960, 800,
1
725, 630. H NMR spectrum, δ, ppm: 1.64 br.s (1H,
CH2NHCH2), 1.87 s (3H, NCCH3), 1.93 s (3H,
3
O=CCH3), 2.78 t (2H, CH2CH2NHC=, J = 6.1 Hz),
3
2.85 t (2H, OCH2CH2NH, J = 4.9 Hz), 3.30 m (2H,
3
CH2NHC=), 3.72 t (2H, OCH2, J = 4.9 Hz), 3.93 d.d
2
3
(1H, cis-CH=CO, J = 1.5, Jcis = 6.6 Hz), 4.12 d.d
2
3
(1H, trans-CH=CO, J = 1.5, Jtrans = 14.4 Hz), 4.91 s
3
(1H, NC=CH), 6.40 d.d (1H, OCH=C, Jcis = 6.6,
3Jtrans = 14.4 Hz), 10.81 br.s (1H, NHC=). 13C NMR
spectrum, δC, ppm: 18.95 (NHCCH3), 28.73 (COCH3),
43.12 (CH2NHC=), 48.42 (CH2CH2NHC=), 49.19
(OCH2CH2NH), 67.20 (OCH2), 86.69 (=CH2), 95.45
(NC=CH), 151.57 (OCH=), 162.88 (NHC=), 194.89
(C=O). Found, %: C 62.44; H 9.72; N 13.82.
C11H20N2O2. Calculated, %: C 62.23; H 9.50; N 13.20.
The fact that the spectra of linear enamino ketones
IVa–IVf contain only one set of signals corresponding
most probably to the cis-s-trans isomer may be inter-
preted in terms of both intramolecular hydrogen
bonding NH···O= and known effect of weakly polar
chloroform-d used as solvent [1].
(E)-4-[2-(2-Hydroxy-3-vinyloxypropylamino)-
ethylamino]pent-3-en-2-one (IVb). Yield 98%, nD20
=
1.5256. IR spectrum, ν, cm–1: 3305, 3116, 3079, 2924,
2871, 1615, 1568, 1520, 1440, 1378, 1357, 1318,
1296, 1236, 1200, 1151, 1081, 1017, 1005, 965, 949,
1
EXPERIMENTAL
818, 744, 653, 612, 546. H NMR spectrum, δ, ppm:
1.89 s (3H, NCCH3), 1.94 s (3H, O=CCH3), 2.62–
2.82 m (6H, CH2NHCH2, OH), 3.31 m (2H,
CH2NHC=), 3.66–3.90 m (3H, OCH2CH), 3.97 d.d
The IR spectra were recorded on a Bruker Vertex-
70 spectrometer from samples prepared as thin films or
1
pelleted with KBr. The H and 13C NMR spectra were
2
3
(1H, cis-CH=CO, J = 1.7, Jcis = 6.7 Hz), 4.16 d.d
2
3
measured at 26°C on a Bruker DPX-400 instrument at
400 and 100 MHz, respectively, using CDCl3 as sol-
vent and hexamethyldisiloxane as internal reference.
(1H, trans-CH=CO, J = 1.7, Jtrans = 14.2 Hz), 4.93 s
3
(1H, NC=CH), 6.43 d.d (1H, OCH=C, Jcis = 6.7,
3Jtrans = 14.2 Hz), 10.93 br.s (1H, NHC=). 13C NMR
spectrum, δC, ppm: 19.05 (NHCCH3), 28.74 (COCH3),
42.85 (CH2NHC=), 48.96 (CH2CH2NHC=), 51.82
(CHCH2NH), 68.31 (CHOH), 70.47 (OCH2), 86.85
Initial 1,3-dicarbonyl compounds IIa, IIb, and III
were commercial products. N-(2-Vinyloxyethyl)-
ethane-1,2-diamine (Ia) was synthesized according to
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010

SYNTHESIS OF ENAMINO KETONES
493
(=CH2), 95.57 (NHC=CH), 151.73 (OCH=), 163.11
(NHC=), 194.85 (C=O). Found, %: C 59.17; H 9.14;
N 11.21. C12H22N2O3. Calculated, %: C 59.48; H 9.15;
N 11.56.
nD20 = 1.5208. IR spectrum, ν, cm–1: 3369, 3299, 3193,
3117, 3081, 2978, 2930, 2903, 2871, 1650, 1606,
1547, 1503, 1458, 1444, 1385, 1364, 1320, 1278,
1201, 1175, 1145, 1095, 1059, 1020, 1006, 979, 965,
1
873, 821, 785, 705, 601, 557. H NMR spectrum, δ,
(E)-3-{2-[2-Hydroxy-3-(2-vinyloxyethoxy)pro-
pylamino]ethylamino}pent-3-en-2-one (IVc). Yield
99%, nD20 = 1.5212. IR spectrum, ν, cm–1: 3310, 3117,
3081, 2922, 2873, 1613, 1574, 1557, 1518, 1454,
1439, 1377, 1357, 1320, 1295, 1201, 1128, 1089,
1036, 1021, 976, 935, 881, 818, 743, 653, 629, 546.
1H NMR spectrum, δ, ppm: 1.92 s (3H, NHCCH3),
1.96 s (3H, O=CCH3), 2.58–2.86 m (6H, CH2NHCH2,
OH), 3.33 m (2H, CH2NHC=), 3.51–3.90 m (7H,
3
ppm: 1.23 t (3H, CH2CH3, J = 7.1 Hz), 1.92 s (3H,
NHCCH3), 2.67–2.85 m (6H, CH2NHCH2, OH),
3.31 m (2H, CH2NHC=), 3.72–3.94 m (3H, OCH2,
2
3
CHOH), 4.02 d.d (1H, cis-CH=CO, J = 1.5, Jcis
=
3
6.6 Hz), 4.08 q (2H, OCH2CH3, J = 7.1 Hz), 4.22 d.d
(1H, trans-CH=CO, J = 1.5, Jtrans 14.2 Hz), 4.46 s
(1H, NHC=CH), 6.49 d.d (1H, OCH=C, Jcis = 6.6,
2
3
3
3Jtrans = 14.2 Hz), 8.79 br.s (1H, NHC=). 13C NMR
spectrum, δC, ppm: 14.73 (OCH2CH3), 19.65
(N H C C H 3 ) , 4 2 . 7 8 ( C H 2 N H C = ) , 4 9 . 3 0
(CH2CH2NHC=), 51.67 (CHCH2NH), 58.47
(OCH2CH3), 68.49 (CHOH), 70.35 (OCH2), 82.78
(NHC=CH), 87.05 (=CH2), 151.76 (OCH=), 161.74
(NHC=), 170.75 (C=O). Found, %: C 57.47; H 8.57;
N 10.60. C13H24N2O4. Calculated, %: C 57.33; H 8.88;
N 10.29.
2
OCH2CH2OCH2CH), 3.98 d.d (1H, cis-CH=CO, J =
3
2
1.7, Jcis = 6.7 Hz), 4.17 d.d (1H, trans-CH=CO, J =
1.7, 3Jtrans = 14.3 Hz), 4.95 s (1H, NHC=CH), 6.45 d.d
3
3
(1H, OCH=C, Jcis = 6.7, Jtrans = 14.3 Hz), 10.89 br.s
(1H, NHC=). 13C NMR spectrum, δC, ppm: 18.61
(NHCCH3), 28.35 (COCH3), 42.53 (CH2NHC=),
48.73 (CH2CH2NHC=), 51.68 (CHCH2NH), 66.94
(=CHOCH2), 68.47 (CHOH), 69.39 (=CHOCH2CH2),
73.77 (OCH2CH), 86.39 (=CH2), 95.08 (NHC=CH),
151.37 (OCH=), 162.69 (NHC=), 194.23 (C=O).
Found, %: C 58.41; H 9.49; N 10.09. C14H26N2O4. Cal-
culated, %: C 58.72; H 9.15; N 9.78.
Ethyl 3-{2-[2-hydroxy-3-(2-vinyloxyethoxy)pro-
pylamino]ethylamino}but-2-enoate (IVf). Yield
99%, nD20 = 1.5139. IR spectrum, ν, cm–1: 3480, 3299,
3193, 3117, 3081, 2977, 2929, 2900, 2873, 1648,
1606, 1540, 1504, 1454, 1444, 1385, 1363, 1321,
1277, 1202, 1174, 1133, 1096, 1058, 1022, 978, 966,
Ethyl (E)-3-[2-(2-vinyloxyethylamino)ethyl-
amino]but-2-enoate (IVd). Yield 99%, nD20 = 1.5128.
IR spectrum, ν, cm–1: 3291, 3194, 3117, 3078, 3044,
2978, 2932, 2901, 2873, 2843, 1650, 1607, 1503,
1462, 1444, 1384, 1364, 1320, 1267, 1199, 1174, 1143,
1096, 1058, 1022, 978, 965, 818, 784, 704, 600, 557.
1
820, 784, 705, 666, 606, 558. H NMR spectrum, δ,
3
ppm: 1.18 t (3H, OCH2CH3, J = 7.1 Hz), 1.87 s (3H,
NHCCH3), 2.55–2.73 m (4H, CHCH2NH, OH), 2.76 t
3
(2H, CH2CH2NHC=, J = 6.0 Hz), 3.26 m (2H,
CH2NHC=), 3.46–3.81 m (7H, OCH23CH2OCH2CH),
3
1H NMR spectrum, δ, ppm: 1.23 t (3H, CH2CH3, J =
2
4.00 d.d (1H, cis-CH=CO, J = 2.0, Jcis = 6.8 Hz),
3
7.1 Hz), 1.46 br.s (1H, CH2NHCH2), 1.92 s (3H,
4.02 q (2H, OCH2CH3, J = 7.1 Hz), 4.14 d.d (1H,
3
2
3
NHCCH3), 2.82 t (2H, CH2CH2NHC=, J = 6.1 Hz),
trans-CH=CO, J = 2.0, Jtrans = 14.3 Hz), 4.40 s (1H,
3
3
3
2.90 t (2H, OCH2CH2NH, J = 5.1 Hz), 3.32 m (2H,
NHC=CH), 6.43 d.d (1H, OCH=C, Jcis = 6.8, Jtrans
=
3
14.3 Hz), 8.70 br.s (1H, NHC=). 13C NMR spectrum,
δC, ppm: 14.63 (OCH2CH3), 19.51 (NHCCH3), 42.77
(CH2NHC=), 49.36 (CH2CH2NHC=), 51.82
(CHCH2NH), 58.25 (OCH2CH3), 67.30 (=CHOCH2),
69.00 (CHOH), 69.83 (=CHOCH2CH2), 74.01
(OCH2CH), 82.56 (NHC=CH), 86.80 (=CH2), 151.73
(OCH=), 161.63 (NHC=), 170.53 (C=O). Found, %:
C 56.41; H 8.59; N 8.49. C15H28N2O5. Calculated, %:
C 56.94; H 8.92; N 8.85.
CH2NHC=), 3.77 t (2H, OCH2, J = 5.1 Hz), 4.00 d.d
2
3
(1H, cis-CH=CO, J = 1.7, Jcis = 6.7 Hz), 4.07 q (2H,
3
OCH2CH3, J = 7.1 Hz), 4.18 d.d (1H, trans-CH=CO,
3
2J = 1.7, Jtrans = 14.3 Hz), 4.45 s (1H, NHC=CH),
3
3
6.46 d.d (1H, OCH=C, Jcis = 6.7, Jtrans = 14.3 Hz),
8.62 br.s (1H, NHC=). 13C NMR spectrum, δC, ppm:
14.58 (OCH2CH3), 19.53 (NHCCH3), 43.00
(CH2NHC=), 48.36 (CH2CH2NHC=), 49.46
(O C H 2 C H 2 N H ) , 5 8 . 2 2 ( O C H 2 C H 3 ) , 6 7 . 1 5
(=CHOCH2), 82.55 (NHC=CH), 86.68 (=CH2), 151.60
(OCH=), 161.62 (NHC=), 170.49 (C=O). Found, %:
C 59.87; H 9.39; N 11.48. C12H22N2O3. Calculated, %:
C 59.48; H 9.15; N 11.56.
5,5-Dimethyl-3-[2-(2-vinyloxyethylamino)ethyl-
amino]cyclohex-2-en-1-one (Va). Yield 99%, mp 54–
56°C. IR spectrum, ν, cm–1: 3221, 3021, 2954, 2937,
2890, 2869, 2840, 1627, 1598, 1567, 1542, 1458,
1451, 1428, 1413, 1383, 1368, 1339, 1331, 1320,
1277, 1255, 1194, 1174, 1155, 1127, 1085, 1073, 1035,
Ethyl (E)-3-[2-(2-hydroxy-3-vinyloxypropyl-
amino)ethylamino]but-2-enoate (IVe). Yield 99%,
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KUKHAREV et al.
494
979, 970, 939, 918, 892, 870, 828, 808, 763, 708, 665,
611, 553, 521, 506. H NMR spectrum, δ, ppm: 1.05 s
1599, 1574, 1536, 1465, 1425, 1413, 1379, 1363,
1321, 1271, 1251, 1202, 1174, 1153, 1127, 1041, 966,
949, 933, 891, 872, 834, 816, 786, 682, 608, 548, 530,
475, 440. H NMR spectrum, δ, ppm: 1.04 s (6H,
CH3), 2.16 s (2H, CH2C=C), 2.17 s (2H, CH2C=O),
1
(6H, CH3), 2.17 s (2H, CH2C=C), 2.19 (2H, CH2C=O),
2.86–2.89 m (5H, CH2NHCH2), 3.13 m (2H,
1
3
CH2NHC=), 3.77 t (2H, OCH2, J = 5.0 Hz), 4.02 d.d
2
3
(1H, cis-CH=CO, J = 1.9, Jcis = 6.7 Hz), 4.20 d.d
2.61–2.81 m (4H, NHCH2CH2NHC=, OH), 2.85 t (2H,
2
3
3
(1H, trans-CH=CO, J = 1.9, Jtrans = 14.3 Hz), 5.08 s
(1H, NHC=CH), 5.14 br.s (1H, NHC=), 6.46 d.d (1H,
CHCH2NH, J = 5.8 Hz), 3.13 m (2H, CH2NHC=),
3.43–3.56 m (2H, OCH2CH), 3.70–3.75 m (2H,
3
3
3
OCH=C, Jcis = 6.7, Jtrans = 14.3 Hz). 13C NMR spec-
trum, δC, ppm: 28.38 (CH3), 32.84 (C5), 41.94 (C4),
43.53 (CH2NHC=), 47.03 (CH2CH2NHC=), 48.05
(OCH2CH2NH), 50.38 (C6), 67.17 (OCH2), 87.05
(=CH2), 95.58 (C2), 151.61 (OCH=), 162.99 (C3),
196.85 (C1). Found, %: C 67.04; H 10.02; N 11.15.
C14H24N2O2. Calculated, %: C 66.63; H 9.59; N 11.10.
=CHOCH2CH2), 3.83 t (2H, =CHOCH2, J = 4.4 Hz),
2
3.90 m (1H, CHOH), 4.02 d.d (1H, cis-CH=CO, J =
3
2
2.1, Jcis = 6.8 Hz), 4.19 d.d (1H, trans-CH=CO, J =
2.1, 3Jtrans = 14.3 Hz), 5.07 s (1H, NHC=CH), 5.27 br.s
(1H, NHC=), 6.46 d.d (1H, OCH=C, Jcis = 6.8,
3
3Jtrans = 14.3 Hz). 13C NMR spectrum, δC, ppm: 28.33
(CH3), 32.77 (C5), 42.13 (C4), 43.43 (CH2NHC=),
47.27 (CH2CH2NHC=), 50.31 (NHCH2CH), 51.66
(C6), 67.30 (=CHOCH2), 69.02 (CHOH), 69.88
(=CHOCH2CH2), 74.07 (OCH2CH), 87.03 (=CH2),
95.43 (C2), 151.64 (OCH=), 163.13 (C3), 196.79 (C1).
Found, %: C 62.41; H 9.49; N 8.19. C17H30N2O4. Cal-
culated, %: C 62.55; H 9.26; N 8.58.
3-[2-(2-Hydroxy-3-vinyloxypropylamino)ethyl-
amino]-5,5-dimethylcyclohex-2-en-1-one (Vb). Yield
99%, mp 112–114°C. IR spectrum, ν, cm–1: 3402,
3290, 3256, 3121, 3075, 2955, 2927, 2865, 1650,
1615, 1600, 1574, 1533, 1462, 1448, 1425, 1413,
1380, 1362, 1341, 1315, 1270, 1251, 1196, 1173, 1152,
1128, 1096, 1046, 1002, 981, 965, 931, 900, 890, 834,
819, 798, 745, 680, 665, 609, 547, 526. 1H NMR spec-
trum, δ, ppm: 1.05 s (6H, CH3), 2.16 s (2H, CH2C=C),
2.19 s (2H, CH2C=O), 2.66–2.82 m (4H, NHCH2CH2-
REFERENCES
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3
NHC=, OH), 2.87 t (2H, CHCH2NH, J = 5.6 Hz),
2. Foster, J.E., Nicholson, J.M., Butcher, R., Stables, J.P.,
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3.16 m (2H, CH2NHC=), 3.65–3.72 m (2H, OCH2),
2
3.97 m (1H, CHOH), 4.03 d.d (1H, cis-CH=CO, J =
3
2
1.8, Jcis = 6.7 Hz), 4.20 d.d (1H, trans-CH=CO, J =
1.8, 3Jtrans = 14.2 Hz), 5.08 s (1H, NHC=CH), 5.39 br.s
(1H, NHC=), 6.47 d.d (1H, OCH=C, Jcis = 6.7,
3
3Jtrans = 14.2 Hz). 13C NMR spectrum, δC, ppm: 28.37
(CH3), 32.85 (C5), 42.18 (C4), 43.55 (CH2NHC=),
47. 33 (CH2CH2NHC=), 50. 33 (C6), 51. 56
(CHCH2NH), 68.54 (CHOH), 70.35 (OCH2), 87.24
(=CH2), 95.59 (C2), 151.59 (OCH=), 163.11 (C3),
196.95 (C1). Found, %: C 63.41; H 9.49; N 9.59.
C15H26N2O3. Calculated, %: C 63.80; H 9.28; N 9.92.
3-{2-[2-Hydroxy-3-(2-vinyloxyethoxy)propyl-
amino]ethylamino}-5,5-dimethylcyclohex-2-en-1-
one (Vc). Yield 99%, mp 62–64°C. IR spectrum, ν,
cm–1: 3359, 3119, 3080, 2954, 2926, 2867, 1635, 1618,
6. Kukharev, B.F., Stankevich, V.K., Lobanova, N.A., Kli-
menko, G.R., and Sadykov, E.Kh., Russ. J. Org. Chem.,
2006, vol. 42, p. 1409.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010