FEDOSEEV et al.
1664
3181, 3080 (NH), 1757–1708 (С=О). 1Н NMR spectrum,
δ, ppm: 1.62 s (3H, CH3), 1.75–1.90 m [6H, (CH2)3],
2.06 d (1H, CH2, J 14.1 Hz), 2.64–2.71 m (1H, CH2),
4.23 s (1H, СH), 11.67 s (1H, NH), 11.83 s (1H, NH).
Mass spectrum, m/z (Irel, %): 278 (27) [M]+. Found, %:
C 56.15; H 5.08; N 10.04. C13H14N2O5. Calculated, %:
C 56.11; H 5.07; N 10.07. M 278.26.
3a-(3-Oxobutan-2-yl)pyrrolo[3,4-c]pyrrole-
1,3,4,6(2H,3aH,5H,6aH)-tetraone (IIb). To a slurry of
0.238 g (1 mmol) of spirane IVa in 1 mL of ethanol was
added 3 mL of conc. HCl (HBr), and the mixture was
boiled for 1 h. The reaction mixture was evaporated, the
formed precipitate was filtered off, washed with water
and 2-propanol, and dried in a vacuum-desiccator over
CaCl2. Yield 0.086 g (36%), mp 256–257°С. IR spectrum,
ν, cm–1: 3238–3150 (NH), 1773–1664 (С=О). 1Н NMR
spectrum, δ, ppm: 1.19 d (3H, CH3, J 7.6 Hz), 2.15 s (3H,
CH3), 3.61 q (1H, CH, J 7.6 Hz), 4.19 s (1H, СH), 11.70
s (1H, NH), 11.95 s (1H, NH). Mass spectrum, m/z (Irel,
%): 238 (7) [M]+. Found, %: C 50.40; H 4.22; N 11.78.
C10H10N2O5. Calculated, %: C 50.42; H 4.23; N 11.76.
M 238.20.
3a-(1-Oxo-1-phenylpropan-2-yl)pyrrolo[3,4-c]-
pyrrole-1,3,4,6(2H,3aH,5H,6aH)-tetraone (IIf). Yield
0.144 g (48%), mp 319–320°С (decomp.). IR spectrum,
ν, cm–1: 3221, 3085 (NH), 1749–1668 (С=О). 1Н NMR
spectrum, δ, ppm: 1.23 d (3H, CH3, J 7.5 Hz), 4.42 s
(1H, СH), 4.51 q (1H, CH, J 7.5 Hz), 7.56 t (2H, C6H5,
J 7.6 Hz), 7.70 t (1H, C6H5, J 7.4 Hz), 7.99 d (2H, C6H5,
J 7.7 Hz), 11.80 s (1H, NH), 12.04 s (1H, NH). Mass
spectrum, m/z (Irel., %): 300 (41) [M]+. Found, %: 59.97;
H 4.02; N 9.36. C15H12N2O5. Calculated, %: C 60.00; H
4.03; N 9.33. M 300.27.
Compounds IIc–IIf were obtained analogously.
3a-(2-Oxopentan-3-yl)pyrrolo[3,4-c]pyrrole-
1,3,4,6(2H,3aH,5H,6aH)-tetraone (IIc). Yield 0.101
g (40%), mp 264–265°С. IR spectrum, ν, cm–1: 3170,
ACKNOWLEDGMENTS
1
3078 (NH), 1746–1668 (С=О). Н NMR spectrum, δ,
ppm: 0.93 t (3H, CH3, J 7.5 Hz), 1.47–1.56 m (1H, CH2),
1.65–1.73 m (1H, CH2), 2.19 s (3H, CH3), 3.58 d.d (1H,
СH, J 6.9, 5.7 Hz), 4.16 s (1H, СH), 11.75 s (1H, NH),
11.97 s (1H, NH). Mass spectrum, m/z (Irel, %): 252 (10)
[M]+. Found, %: C 52.39; H 4.81; N 11.08. C11H12N2O5.
Calculated, %: C 52.38; H 4.80; N 11.11. M 252.22.
The study was carried out under the financial support
of the Russian Foundation for Basic Research (grant no.
12-03-31600 mol_a).
REFERENCES
3a-(2-Methyl-3-oxobutan-2-yl)pyrrolo[3,4-c]-
pyrrole-1,3,4,6(2H,3aH,5H,6aH)-tetraone (IId).
Yield 0.103 g (41%), mp 335–336°С. IR spectrum ν,
1. Negoro, T., Murata, M., Ueda, Sh., Fujitani, B., OnoYo.,
Kuromiya, A., Komiya, M., Suzuki, K., and Matsumoto,
J., J. Med. Chem., 1998, vol. 41, p. 4118.
2. Frost, J.M., Dart, M.J., Tietje, K.R., Garrison, T.R., Gray-
son, G.K., Daza, A.V., El-Kouhen, O.F., Yao, B.B., Hsieh,
G.C., Pai, M., Zhu, Ch.Z., Chandran, P., and Meyer, M.D.,
J. Med. Chem., 2010, vol. 53, p. 295.
1
cm–1: 3187, 3076 (NH), 1763–1702 (С=О). Н NMR
spectrum, δ, ppm: 1.42 s (6H, 2CH3), 2.12 s (3H, CH3),
4.19 s (1H, СH), 11.74 s (2H, 2NH). Mass spectrum, m/z
(Irel, %): 252 (18) [M]+. Found, %: C 52.41; H 4.79; N
11.10. C11H12N2O5. Calculated, %: C 52.38; H 4.80; N
11.11. M 252.22.
3. Middleton, W.J. and Engelhardt, V.A. J. Am. Chem. Soc.,
1958, vol. 80, p. 2788.
4. De, Jongh, H.A.P., De, Jonge, C.R.H.I., and Mijs, W.J. J.
Org. Chem., 1971, 36, p. 3160.
5. Nasakin, O.E., Lyshchikov, A.N., Pavlov, V.V., Shishkin,
O.V., Nesterov, V.N., Khrustalev, V.N., Antipin, M.Yu.,
and Urman, Ya.G., Russ. J. Org. Chem., 1999, vol. 35, p.
1368.
6. Ershov, O.V. Lipin, K.V., Maksimova, V.N., Eremkin,A.V.,
Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem.,
2009, vol. 45, p. 484.
7. Belikov, M.Yu., Ershov, O.V., Lipovskaya, I.V., Nasakin,
O.E., Sattarova, L.F., Strunin, B.P., Antipov, V.A., and
Gurevich, P.A., Vestn. Kazan. Tekhn. Univ., 2010, vol. 9,
p. 112.
Crystallographic parameters of compound IId: a
8.6964(6), b 12.5540(6), c 20.4979(10) Å, V 2237.9(2) Å3,
Z 8, space group Pbca. The calculation of positions and
thermal parameters of nonhydrogen atoms was performed
in the full-matrix anisotropic approximation. The posi-
tions of the hydrogen atoms were determined from the
Fourier difference synthesis and refined freely and also
calculated and refined in isotropic approximation in
the rider model. The divergence factor R 0.044. CCDC
940654.
3a-(1-Methyl-2-oxocyclohexyl)pyrrolo[3,4-c]-
pyrrole-1,3,4,6(2H,3aH,5H,6aH)-tetraone (IIe). Yield
0.097 g (35%), mp 312–313°С. IR spectrum ν, cm–1:
8. Gurevich, P.A., Fedoseev, S.V., Lipin, K.V., Ershov, O.V.,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013