IEVLEV et al.
1.25 t (3H, 2CH3, J 7.1 Hz),* 1.29–1.33 t (3H, 2CH3, J
750
C6
C1
7.1 Hz), 1.81–2.49 m (8H, 4CH2),* 1.81–2.49 m (8H,
4CH2), 3.14–3.18 d.d (1Н, СН, J 7.2, 17.5 Hz), 3.21–
3.27 d.d (1H, CH, J 7.3, 17.1 Hz),* 4.23–4.27 q (4H,
2OCH2, J 7.12 Hz),* 4.35–4.40 q (4H, 2OCH2, J 7.1 Hz),
5.38 s (1H, CH),* 5.70 s (1H, CH). Found, %: С 58.74;
H 5.97; N 9.25. C15H18N2O5. Calculated, %: C 58.82;
H 5.92; N 9.15. M 306.12.
C5
C4
O1
C3
C2
C7
N2
C16
C13
C12
C11
N1
O3
O5
Diethyl 2,3-dicyano-2-(2-oxocyclohexyl)succinate
(IIe). Yield 1.17 g (73%), mp 120–121°С (decomp.).
O2
1
IR spectrum, ν, cm–1: 2257 (C≡N), 1737 (C=O). Н
C14
C8
C15
C10
O4
NMR spectrum (DMSO-d6), δ, ppm: 1.21–1.25 t (3H,
2CH3, J 7.1 Hz), 1.24–1.27 t (3H, 2CH3, J 7.1 Hz),*
1.60–2.63 m (8H, 4CH2),* 1.60–2.63 m (8H, 4CH2),
3.37–3.40 d.d (1Н, СН, J 7.3, 17.8 Hz), 3.52–3.49 d.d
(1H, CH, J 7.2, 17.4 Hz),* 4.21–4.25 q (4H, 2OCH2, J
7.11 Hz), 4.22–4.27 m (4H, 2OCH2),* 5.21 s (1H,
CH),* 5.64 s (1H, CH). Found, %: С 60.07; Н 6.19; N
8.81. C16H20N2O5. Calculated, %: C 59.99; H 6.29; N
8.74. M 320.14.
C9
Molecular structure of diethyl 2,3-dicyano-2-(2-
oxocyclohexyl)succinate (IIe) according to XRD data.
3.81 s (3H, OCH3),* 3.82 s (3H, OCH3),* 3.83 s (3H,
OCH3), 5.27 s (1H, CH),* 5.46 s (1H, CH). Found, %:
С 54.21; H 5.25; N 10.59. C12H14N2O5. Calculated, %:
C 54.13; H 5.30; N 10.52. M 266.09.
The purity of compounds obtained was checked by
TLC on Silufol-UV-254 plates, eluent ethyl acetate,
development under UV irradiation, in iodine vapor, or
by thermal decomposition. IR spectra were recorded
on a Fourier IR spectrophotometer FSM-1202 from
Compounds IIb–IIe were obtained similarly.
Dimethyl 2,3-dicyano-2-(2-oxocyclohexyl)suc-
cinate (IIb). Yield 1.11 g (76%), mp 165–168°С
(decomp.). IR spectrum, ν, cm–1: 2257 (C≡N), 1745
1
thin film (mull in mineral oil). Н NMR spectra were
1
(C=O). Н NMR spectrum (DMSO-d6), δ, ppm: 1.21–
registered on a spectrometer Bruker DRX-500,
operating frequency 500.13 MHz, solvent DMSO-d6,
internal reference TMS. Elemental analysis was
carried out on an analyzer Laboratorni Pristroje. XRD
study of a single crystal of compound IIe was carried
out on a diffractometer StadiVari Pilatus 100K (STOE
Co), MoKα radiation. Data collection, determination
and refining of the unit cell parameters, and the
processing of the diffraction data were carried out
applying the program package STOE X-Area. The
structure was solved by the direct method using
SHELXS-97 software [11]. The XRD study was
carried out using the equipment purchased from the
funds of the Program of development of Moscow
University and within the framework of the Agreement
on collaboration between the Chemical Department of
the Lomonsov Moscow State University and the
Chemical-Pharmaceutical Department of the I.N.
Ul’yanov Chuvash State University.
2.63 m (8H, 4CH2),* 1.21–2.63 m (8H, 4CH2), 3.39–
3.41 d.d (1Н, СН, J 7.3, 17.2 Hz), 3.54–3.50 d.d (1H,
CH, J 7.3, 17.3 Hz),* 3.78 s (3H, OCH3), 3.79 s (3H,
OCH3),* 3.81 s (3H, OCH3), 3.82 s (3H, OCH3),* 5.23
s (1H, CH),* 5.64 s (1H, CH). Found, %: С 57.59; H
5.48; N 9.65. C14H16N2O5. Calculated, %: C 57.53; H
5.52; N 9.58. M 292.11.
Dimethyl 2,3-dicyano-2-(2-oxocycloheptyl)suc-
cinate (IIc). Yield 1.07 g (70%), mp 139–141°С
(decomp.). IR spectrum, ν, cm–1: 2257 (C≡N), 1748
1
(C=O). Н NMR spectrum (DMSO-d6), δ, ppm: 1.21–
2.63 m (10H, 5CH2),* 1.23–2.63 m (10H, 5CH2), 3.52–
3.56 m (1H, CH), 3.52–3.56 m (1H, CH),* 3.78 s (3H,
OCH3), 3.79 s (3H, OCH3),* 3.83 s (3H, OCH3), 3,85 s
(3H, OCH3),* 5.24 s (1H, CH),* 5.43 s (1H, CH).
Found, %: С 58.72; H 5.99; N 9.21. C15H18N2O5.
Calculated, %: C 58.82; H 5.92; N 9.15. M 306.12.
Diethyl 2,3-dicyano-2-(2-oxocyclopentyl)suc-
cinate (IId). Yield 1.09 g (71%), mp 115–117°С
(decomp.). IR spectrum, ν, cm–1: 2256 (C≡N), 1736
The study was performed in the framework of the
basic part of the State contract with the Ministry of
Education and Science of the Russian Federation.
1
(C=O). Н NMR spectrum (DMSO-d6), δ, ppm: 1.23–
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 5 2014