VASYUNKINA et al.
744
1H NMR spectrum, d, ppm: 1.4 t (3H, CH3), 2.3 s (6H,
2CH3), 4.3 m (2H, CH2), 5.1 s (1H, CH), 6.78.2 m (6H,
thioph.), 7.28.0 m (10H, 2C6H5), 8.5 s (1H, CH). Found,
%: C 66.36; H 4.45; N 11.01. C35H29N5O3S. Calculated,
%: C 66.56; H 4.60; N 11.09.
8.0 m (10H, 2C6H5). Found, %: C 68.65; H 5.30; N 12.48.
C25H23N4O3. Calculated, %: C 68.97; H 5.29; N 12.87.
b. A mixture of 0.99 ml (12 mmol) of furfural and
1.28 ml (12 mmol) of ethyl cyanoacetate in 40 ml of
ethanol was heated to 40°C and a solution of 2 g
(12 mmol) of compound I in 40 ml of ethanol and 0.1 ml
of diethylamine was added. The mixture was stirred at
70°C for 40 min and was left overnight. On the next day
the separated precipitate was isolated as described for
procedure a. Yield 2.1 g (85%), mp 165°C (from 45%
ethanol). IR and 1H NMR spectra were identical to those
of compound prepared along procedure a. No depression
of the melting point was observed for a mixture of
samples prepared by methods a and b.
c. A mixture of 1 g (4 mmol) of compound VI and
0.64 ml (6 mmol) of ethyl cyanoacetate in 40 ml of ethanol
was heated to 40°C, 0.1 ml of diethylamine was added,
and the mixture was left standing for 2 h. On the next
day the separated precipitate was isolated as described
for procedure a. Yield 0.6 g (72%), mp 165°C (from
45% ethanol). IR and 1H NMR spectra were identical to
those of compounds prepared along procedures a and
b. No depression of the melting point was observed for
a mixture of samples prepared by methods a and c and
also b and c.
3,5-Dimethyl-4-(2-thienyl)-1,7-diphenyl-4,8-
dihydropyrano[2,3-c, 5,6-c]dipyrazole (V). A solution
of 0.1 g (0.14 mmol) of the molecular complex of
compound V with piperidine in 15 ml of 35% ethanol was
heated to boiling. On cooling the separated precipitate
was filtered off and washed with ethanol. Yield 0.55 g
1
(82%), mp 180°C. IR spectrum, cm : 740, 940, 1090,
1
1210, 1280, 1415, 1510, 1600, 2850. H NMR spectrum
,
d, ppm: 2.3 s (6H, 2CH3), 5.1 s (1H, CH), 6.78.0 m
(3H, thioph.), 7.28.0 m (10H, 2C6H5). Found, %:
C 70.66; H 4.80; N 13.19. C25H20N4OS. Calculated, %:
C 70.75; H 4.72; N 13.21.
3-Methyl-1-phenyl-4-furfurylidene-5-pyrazolone
(VI). In 35 ml of ethanol was dissolved at heating 1 g
(5.7 mmol) of compound I and 0.47 ml (5.7 mmol) of
furfural. One drop of diethylamine was added, and the
mixture was stirred for 1 h at 70°C. On cooling the
separated precipitate was filtered off and washed with
ethanol. Yield 0.6 g (44%), mp 105°C. IR spectrum,
1
cm : 760, 800, 980, 1100, 1480, 1500, 1620, 1700. Found,
REFERENCES
%: C 71.24; H 4.68; N 11.06. C15H12N2O2. Calculated,
%: C 71.43; H 4.76; N 11.11.
1. Sharanina, L.G., Marshtupa, V.P., and Sharanin, Yu.A., Khim.
Geterotsikl. Soed., 1980, p. 1420.
2. Nawwar, G. A. M., Abdelrazek, F. M., and Swellam, R.H.,
Arch. Pharm., 1991, vol. 324, p. 875.
3. Abdelrazek, F. M., Kandeel, Z. E. S., Himly, K. , M. H., and
Elnagdi, M. H., Synthesis, 1985, p. 432.
4. Sharanin, Yu.A., Sharanina, L.G., and Puzanova, V.V., Zh.
Org. Khim., 1983, vol. 19, p. 2609.
3,5-Dimethyl-4-(2-furyl)-1,7-diphenyl-4,8-
dihydropyrano[2,3-c, 5,6-c]dipyrazole (complex with
water) (VII). a. A mixture of 0.46 g (2.62 mmol) of
compound I, 0.5 g (2.62 mmol) of 1-ethoxycarbonyl-2-
(2-furyl)acrylonitrile, and 0.01 ml of diethylamine in
18 ml of ethanol was stirred for 80 min at 50°C. The
solution was evaporated by ~1/3 of its volume, the
separated precipitate was filtered off, washed with
ethanol, and dried in a vacuum desiccator. Yield 0.43 g
(74%), mp 165°C (from 45% ethanol). IR spectrum,
5. Tacconi, G., Gatti, G., Desimoni, G., and Messori, V., J. Pract.
Chem., 1980, vol. 322, p. 831.
6. Abdel-Latif, F. F., Z. Naturfors. B, 1990, vol. 45, p. 1675.
7. Sharanina, L.G., Promonenkov, V.K., Marshtupa, V.P.,
Pashchenko, A.V., , Puzanova, V.V., Sharanin, Yu.A., Klyu-
ev, N.A., Gusev, L.F., and Gnatusina,A.P., Khim. Geterotsikl.
Soed., 2004, p. 801.
1
cm : 810, 880, 1020, 1080, 1200, 1290, 1400, 1510, 1610,
1
1800, 2940, 3400. H NMR spectrum, d, ppm: 2.2 s (6H,
2CH3), 4.9 s (1H, CH), 6.06.5 m (3H, furan), 7.0
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 5 2005