THREE-COMPONENT HETEROCYCLIZATION OF 2-BENZYLIDENEMALONONITRILE
625
using benzene (VI, VIII) or chloroform (VII, IX) as
eluent.
[M – CN – C2H2]+, 167 (5) [M – C6H5]+, 91 (58)
[C7H7]+. Found, %: C 83.42; H 4.74; N 11.29.
C17H12N2. Calculated, %: C 83.61; H 4.92; N 11.48.
M 244.31.
2-(3,4-Dimethoxyphenyl)-1-methyl-4-phenyl-1H-
pyrrole-3-carbonitrile (VI). Yield 41%, mp 95–97°C.
IR spectrum (CHCl3): ν 2230 cm–1 (C≡N). UV spec-
The IR spectra were recorded on an IKS-29 spec-
trometer from solutions in chloroform with a concen-
1
trum, λmax, nm (logε): 245 (4.28), 373 (4.43). H NMR
1
spectrum, δ, ppm: 7.62–7.65 d (1H, Harom), 7.48 m
tration of 40 mg/ml using 0.1-mm cells. The H NMR
(5H, Harom), 7.20–7.23 d (1H, Harom), 7.10 s (1H,
spectra were measured on a Tesla BS-487C spectrom-
eter (80 MHz) using acetone-d6 as solvent and hexa-
methyldisiloxane as internal reference. The electronic
absorption spectra were obtained on an SF-8 spectro-
photometer from solutions in carbon tetrachloride. The
mass spectra (electron impact, 70 eV) were recorded
on a Finnigan SSQ-7000 instrument with direct sample
admission into the ion source (vaporizer temperature
90–150°C). The progress of reactions and the purity of
products were monitored by TLC on Silufol UV-254
plates using acetone–hexane (2:3) as eluent; develop-
ment with iodine vapor.
H
arom), 6.70 s (1H, CH), 3.85 s (3H, CH3O), 3.80 s
(3H, CH3O), 3.77 s (3H, CH3). Mass spectrum, m/z
(Irel, %): 317 (22) [M – 1]+, 303 (16) [M – CH3]+, 292
(47) [M – CN]+, 287 (10) [M – CH3O]+, 190 (100)
[M – CN – C8H6]+, 130 (7) [M – CN – C10H10O2]+, 91
(60) [C7H7]+. Found, %: C 75.24; H 5.45; N 8.67.
C20H18N2O2. Calculated, %: C 75.47; H 5.66; N 8.81.
M 318.38.
1-Methyl-4-phenyl-1H-pyrrole-3-carbonitrile
(VII). Yield 53%, mp 135–137°C. IR spectrum
(CHCl3): ν 2230 cm–1 (C≡N). UV spectrum, λmax, nm
1
(logε): 245 (4.29), 310 (4.41). H NMR spectrum, δ,
REFERENCES
ppm: 7.46 m (5H, Harom), 7.05 s (1H, CH), 6.72 s (1H,
CH), 3.76 s (3H, CH3). Mass spectrum, m/z (Irel, %):
181 (25) [M – 1]+, 168 (20) [M – CH3]+, 130 (100)
[M – CN – C2H2]+, 91 (55) [C7H7]+. Found, %:
C 78.94; H 5.32; N 15.21. C12H10N2. Calculated, %:
C 79.12; H 5.49; N 15.39. M 182.24.
1. Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V.,
Osnovy organicheskoi khimii lekarstvennykh veshchestv
(Principles of Organic Chemistry of Drugs), Moscow:
Mir, 2007, p. 107.
2. Granik, V.G., Osnovy meditsinskoi khimii (Foundations of
Medicinal Chemistry), Moscow: Vuzovskaya Kniga,
2001, p. 278.
3. Baran’ski, A. and Kelarev, V.I., Khim. Geterotsikl.
Soedin., 1990, p. 435.
4. Zlotin, S.G., Varnaeva, G.N., and Luk’yanov, O.A., Usp.
Khim., 1989, vol. 58, p. 796.
2-(3,4-Dimethoxyphenyl)-1,4-diphenyl-1H-pyr-
role-3-carbonitrile (VIII). Yield 51%, mp 162–
163°C. IR spectrum (CHCl3): ν 2230 cm–1 (C≡N). UV
spectrum, λmax, nm (logε): 245 (4.25), 380 (4.42).
1H NMR spectrum, δ, ppm: 7.52 m (10H, Harom), 7.63–
7.66 d (1H, Harom), 7.20–7.24 d (1H, Harom), 7.12 s (1H,
Harom), 6.71 s (1H, CH), 3.85 s (3H, CH3O), 3.80 s
(3H, CH3O). Mass spectrum, m/z (Irel, %): 379 (20)
[M – 1]+, 354 (35) [M – CN]+, 349 (10) [M – CH3O]+,
303 (6) [M – C6H5]+, 252 (100) [M – CN – C8H6]+, 192
(20) [M – CN – C10H10O2]+, 91 (62) [C7H7]+. Found,
%: C 78.74; H 5.06; N 7.18. C25H20N2O2. Calculated,
%: C 78.95; H 5.26; N 7.37. M 380.45.
5. Parham, W.E. and Bleasdale, J.L., J. Am. Chem. Soc.,
1951, vol. 73, p. 4664.
6. Schubert-Zsilavecz, M., Vichelitsch, A., Likussar, W., and
Gusterhuber, D., Justus Liebigs Ann. Chem., 1993,
p. 147.
7. Perekalin, V.V. and Sopova, A.S., Nepredel’nye nitro-
soedineniya (Unsaturated Nitro Compounds), Moscow:
Khimiya, 1966, p. 194.
8. Structure Determination of Organic Compounds. Tables
of Spectral Data, Pretsch, E., Bühlmann, P., and Af-
folter, C., Eds., Berlin: Springer, 2000, 3rd ed. Translated
under the title Opredelenie stroeniya organicheskikh
soedinenii. Tablitsy spektral’nykh dannykh, Moacow:
Mir, 2006, p. 195.
1,4-Diphenyl-1H-pyrrole-3-carbonitrile (IX).
Yield 55%, mp 157–158°C. IR spectrum (CHCl3):
ν 2230 cm–1 (C≡N). UV spectrum, λmax, nm (logε): 245
1
(4.26), 320 (4.40). H NMR spectrum, δ, ppm: 7.51 m
(10H, Harom), 7.06 s (1H, CH), 6.74 s (1H, CH). Mass
spectrum, m/z (Irel, %): 243 (15) [M – 1]+, 192 (100)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 4 2009