CASCADE CYCLIZATION OF 1,2-DIAMINO-4-PHENYLIMIDAZOLE
277
6.75–7.01 m (7Н, С6Н5, NH2), 7.24–7.85 d.d (4Н, С6Н4,
J 8.0, 8.0 Hz). Mass spectrum: m/z (Irel, %): 427.52 (100)
[M]+, 381 (12), 140 (15), 77 (25). Found, %: С 67.15;
Н 5.37; N 16.35. С24Н21N5O3. Calculated, %: С 67.15;
Н 5.36; N 16.32.
7.10–7.50 d.d (4Н, С6Н4, J 7.8 Hz), 7.22 m (5Н, С6Н5).
Mass spectrum: m/z (Irel, %): 392.45 [M + 2]+ (27), 390.45
[M]+ (80), 279 (100), 139 (15), 111 (18), 77 (24). Found,
%: С 67.60; Н 4.85; N 14.35. С22Н19СlN4O. Calculated,
%: С 67.61; Н 4.87; N 14.34.
Reaction of 1,2-diamino-4-phenylimidazole
(I) with benzaldehydes IIа, IIb, IId, IIe, IIg and
1,3-cyclohexanedione (IV). A mixture of 2 mmol of
amine I, 2 mmol of an appropriate aldehyde IIа, IIb, IId,
IIe, IIg, and 2 mmol of 1,3-cyclohexanedione (IV) in
5 ml of methanol was boiled for 2 h. The reaction mixture
was cooled, compound VI was filtered off.
3-Amino-1-phenyl-10-(4-nitrophenyl)-7,8-dihydro-
imidazo[1,5-b]cinnolin-9(5Н,6Н,10Н)-one (VIg). Yield
1.2 mmol (60%), mp 208–210°С (decomp.). IR spectrum,
cm–1: 3340–2872 (NH2, CH2), 1676 (СО), 1344 (NО2).
1Н NMR spectrum, δ, ppm: 1.79 m (2Н, СН2), 2.40 m
(4Н, СН2), 5.53 s (1Н, С10Н), 5.91 br.s (2Н, NH2), 7.25 m
(5Н, С6Н5), 8.04, 7.37 d.d (4Н, С6Н4, J 8.2, 8.2 Hz).
Found, %: С 65.83; Н 4.74; N 17.47. С22Н19N5O3.
Calculated, %: С 65.84; Н 4.74; N 17.46.
3-Amino-1,10-diphenyl-7,8-dihydroimidazo-[1,5-b]
cinnolin-9(5Н,6Н,10Н)-one (VIа). Yield 1.5 mmol
(74%), mp 188–190°С (decomp.). IR spectrum, cm–1:
1
3428–2844 (NH2, CH2), 1688 (СО). Н NMR spectrum,
REFERENCES
δ, ppm: 1.80 m (2Н, СН2), 2.36 m (4Н, СН2), 5.40 s (1Н,
С10Н), 5.75 br.s (2Н, NH2), 7.00–7.56 m (10Н, С6Н5,
С6Н5). Mass spectrum: m/z (Irel, %): 356.46 (100) [M]+,
279 (15), 176 (10), 103 (12), 77 (10). Found, %: С 74.19;
Н 5.63; N 15.71. С22Н20N4O. Calculated, %: С 74.16;
Н 5.62; N 15.73.
1. Orlov, V.D., Papiashvili, I.Z., Povstyanoi, M.V., Id-
zikovskii, V.A., and Tsyguleva, O.M., Khim. Geterotsikl.
Soedin., 1983, p. 93.
2. Povstyanoi, V.M., Klyuev, N.A., Dank, E.Kh., Idzikovskii,
V.A., and Kruglenko, V.P., Zh. Org. Khim., 1983, vol. 19,
p. 433.
3-Amino-1-phenyl-10-(4-methylphenyl)-7,8-
dihydroimidazo[1,5-b]cinnolin-9(5Н,6Н,10Н)-one
(VIb). Yield 1.3 mmol (65%), mp 187–189°С (decomp.).
IR spectrum, cm–1: 3432–2872 (NH2, CH2), 1688 (СО).
1Н NMR spectrum, δ, ppm: 1.79 m (2Н, СН2), 2.15 s (3Н,
СН3), 2.36 m (4Н, СН2), 5.35 s (1Н, С10Н), 5.71 br.s (2Н,
NH2), 6.98–7.26 m (5Н, С6Н5), 7.20–7.55 d.d (4Н, С6Н4,
J 7.4 Hz). Mass spectrum: m/z (Irel, %): 370.49 (100) [M]+,
293 (13), 260 (10), 196 (10), 155 (13), 119 (17), 91 (43),
77 (11). Found, %: С 74.62; Н 5.95; N 15.15. С23Н22N4O.
Calculated, %: С 74.60; Н 5.95; N 15.14.
3. Kolos, N.N., Orlov, V.D., Paponov, B.V., and Shishkin, O.
V., Khim. Geterotsikl. Soedin., 1999, p. 1388.
4. Kolos, N.N., Orlov, V.D., Paponov, B.V., Baumer, V.N., and
Shishkin, O.V., Khim. Geterotsikl. Soedin., 1998, p. 1397.
5. Kolos, N.N., Beryozkina, T.V., and Orlov, V.D., Mendeleev
Commun., 2002, vol. 12, p. 91.
6. Lipson, V.V., Svetlichnaya, N.V., Shishkina, S.V., and
Shishkin, O.V., Mendeleev Commun., 2008, vol. 18, p. 141.
7. Kolos, N.N., Orlov, V.D., Paponov, B.V., Kvashnitskaya,
N.A., Baumer, V.N., and Shishkin, O.V., Khim. Geterotsikl.
Soedin., 1999, p. 796.
3-Amino-1-phenyl-10-(4-dimethylaminophenyl)-
7,8-dihydroimidazo[1,5-b]cinnolin-9(5Н,6Н,10Н)-one
(VId). Yield 1.2 mmol (62%), mp 218–220°С (decomp.).
IR spectrum, cm–1: 3492–2796 (NH2, CH2), 1688 (СО).
1Н NMR spectrum, δ, ppm: 1.79 m (2Н, СН2), 2.36 m
(4Н, СН2), 2.76 s (6Н, СН3), 5.36 s (1Н, С10Н), 5.68 br.s
(2Н, NH2), 6.51–7.23 m (5Н, С6Н5), 6.93–7.57 d.d (4Н,
С6Н4, J 7.6, 7.6 Hz). Found, %: С 72.23; Н 6.75; N 15.59.
С24Н25N5O. Calculated, %: С 72.18; Н 6.27; N 17.54.
8. Kolos, N.N., Orlov, V.D., Paponov, B.V., Khim. Get-
erotsikl. Soedin., 2001, p. 368.
9. Krimer, M.Z., Makaev, F.Z., Styngach, E.P., Koretskii,
A.G., Pogrebnoi, S.I., and Kochug,A.I.., Khim. Geterotsikl.
Soedin., 1996, p. 1209.
10. Gyoergydeak, Z., Szabo, G., and Holzer, W., Monatsh.
Chem., 2004, vol. 135, p. 173.
11. Burgi, H.-B. and Dunitz, J.D., Structure Correlation,
3-Amino-1-phenyl-10-(4-chlorophenyl)-7,8-
dihydroimidazo[1,5-b]cinnolin-9(5Н,6Н,10Н)-one
(VIe). Yield 1.4 mmol (72%), mp 228–230°С (decomp.).
IR spectrum, cm–1: 3340–2872 (NH2, CH2), 1672 (СО).
1Н NMR spectrum, δ, ppm: 1.79 m (2Н, СН2), 2.36 m
(4Н, СН2), 5.40 s (1Н, С10Н), 5.78 br.s (2Н, NH2),
Weinheim: VCH, 1994, vol. 2, p. 741.
12. Zefirov, N.S., Palyulin, V.A., and Dashevskaya, E.E.
J. Phys. Org. Chem., 1990, vol. 3, p. 147.
13. Zefirov, Yu.V. Kristallografiya., 1997, vol. 42, p. 936.
14. Sheldrick, G.M. Acta, Cryst. A., 2008, vol. 64, p. 112.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 2 2012