VELIKORODOV et al.
404
Scheme 3.
O
O
O
O
O
Me
Me
O
+
MeNHCH2COOH
N
O
N
–H2O
–CO2
CH2
O–
O
IR spectra (4000 to 400 cm–1) were measured on
an InfraLUM FT-02 spectrometer with Fourier trans-
form from samples prepared as KBr pellets. The purity
of the isolated compounds was checked by thin-layer
chromatography using Silufol UV-254 plates; spots
were detected by treatment with iodine vapor.
Methyl 4-[(1′-methyl-1,2″,3-trioxo-1,1″,2″,3-
tetrahydrodispiro[indole-2,2′-pyrrolidine-3′,3″-in-
dol]-4′-yl)carbonyl]phenylcarbamate (IV). A mix-
ture of 1.13 g (3.5 mmol) of chalcone I, 0.31 g
(3.5 mmol) of sarcosine, and 0.69 g (3.5 mmol) of
ninhydrin in 15 ml of methanol–water (3:1 by volume)
was heated for 24 h under reflux. The mixture was
cooled and poured into 50 ml of water, and the precip-
itate was filtered off, dried in air, and purified by chro-
matography on a glass column charged with activated
silica gel (Silicagel, 100–400 μm) using acetone as
eluent. Yield 1.29 g (72%), light brown crystals,
mp 222–224°C. IR spectrum, ν, cm–1: 3370, 3340
(NH); 1720, 1705 (C=O); 1620, 1575, 1565 (C=Carom).
1H NMR spectrum, δ, ppm: 2.80 s (3H, NMe), 3.71 s
(3H, OMe), 3.86–3.88 m and 4.35–4.38 m (1H each,
5′-H), 4.45 t (1H, 4′-H, J = 7.2 Hz), 7.20–7.35 m (5H,
Methyl 4-[(1′-methyl-2,2″-dioxo-1,1″,2,2″-tetra-
hydrodispiro[indole-3,2′-pyrrolidine-3′,3″-indol]-
4′-yl)carbonyl]phenylcarbamate (II). A mixture of
1.13 g (3.5 mmol) of chalcone I, 0.31 g (3.5 mmol) of
sarcosine, and 0.52 g (3.5 mmol) of isatin in 25 ml of
aqueous propan-2-ol (3:2 by volume) was heated for
8 h under reflux. After cooling, the precipitate was
filtered off, dried in air, and recrystallized from
propan-2-ol. Yield 1.24 g (73%), colorless crystals,
mp 256–258°C. IR spectrum, ν, cm–1: 3380, 3340
(NH); 1718, 1710 (C=O); 1620, 1580, 1575 (C=Carom).
1H NMR spectrum, δ, ppm: 2.49 s (3H, NMe), 3.71 s
(3H, OMe), 3.85–3.88 m (1H, 5′-H), 4.10 t (1H, 4′-H,
J = 8.20 Hz), 4.38–4.43 m (1H, 5′-H), 6.97–7.23 m
(8H, Harom), 7.76 d (1H, Harom, J = 8.6 Hz), 7.94 d (1H,
Harom), 7.71 d (2H, Harom, J = 7.4 Hz), 7.81 d (1H, Harom
,
J = 7.2 Hz), 8.19–8.25 m (2H, Harom), 8.43 d (2H,
Harom, J = 8.6 Hz), 9.52 br.s (1H, NHCO2Me), 10.46 s
(1H, NHCO). Found, %: C 68.22; H 4.35; N 7.99.
C29H23N3O6. Calculated, %: C 68.37; H 4.52; N 8.25.
H
arom, J = 8.6 Hz), 8.38 d (2H, Harom, J = 8.6 Hz),
9.54 br.s (1H, NHCO2Me), 10.21 s (2H, NHCO).
Found, %: C 67.55; H 4.86; N 11.08. C28H24N4O5. Cal-
culated, %: C 67.74; H 4.84; N 11.29.
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chalcone I, 0.40 g (3.5 mmol) of L-proline, and 0.52 g
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1′-H, J = 8.8 Hz), 6.97–7.32 m (8H, Harom), 7.41 d (1H,
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NHCO2Me), 10.54 s (2H, NHCO). Found, %: C 68.82;
H 5.01; N 10.63. C30H26N4O5. Calculated, %: C 68.97;
H 4.98; N 10.73.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 3 2011