AVDEENKO et al.
936
N-[2,5-Dibromo-3-methyl-4-oxo-6-(propan-2-yl)-
2,5-dien-1-yl]benzimidamide (XXVb). Yield 75%,
1
cyclohexa-2,5-dien-1-ylidene]-N′-(phenylsulfonyl)-
mp 155–157°C. H NMR spectrum (CDCl3), δ, ppm:
1
benzimidamide (XXIVa). H NMR spectrum
0.98 d and 1.20 d (3H each, 3-CHMe2, J = 6.9 Hz),
2.17 s (3H, 6-Me), 3.03 s (3H, MeO), 3.21–3.29 m
(1H, 3-CH), 5.97 s (1H, NH), 7.35 d (2H, 3′-H, 5′-H,
J = 8.9 Hz), 7.49–7.73 m (5H, Ph), 7.53 d (2H, 2′-H,
6′-H, J = 8.9 Hz). Found, %: Br+Cl 30.78, 30.89;
N 4.40, 4.52; S 5.00, 5.10. C24H23Br2ClN2O4S. Calcu-
lated, %: Br+Cl 30.95; N 4.44; S 5.08.
(CDCl3), δ, ppm: 1.48 d.d (6H, 6-CHMe2, J = 7.2,
18 Hz), 2.24 s (3H, 3-Me), 3.76–3.85 m (1H, 6-CH),
7.43–7.96 m (10H, Ph).
N-[2,5-Dibromo-3-methyl-4-oxo-6-(propan-2-yl)-
cyclohexa-2,5-dien-1-ylidene]-N′-(4-methylphenyl-
sulfonyl)benzimidamide (XXIVb). Yield 68%,
1
mp 117–118°C. H NMR spectrum (CDCl3), δ, ppm:
REFERENCES
1.47 d.d (6H, 6-CHMe2, J = 7.2, 18 Hz), 2.24 s (3H,
3-Me), 2.42 s (3H, MeC6H4), 3.76–3.85 m (1H, 6-CH),
7.29 d (2H, 3′-H, 5′-H, J = 8.1 Hz), 7.43–7.78 m (5H,
Ph), 7.88 d (2H, 2′-H, 6′-H, J = 8.1 Hz). Found, %:
Br 27.64, 27.80; N 4.53, 4.69; S 5.16, 5.31.
C24H22Br2N2O3S. Calculated, %: Br 27.63; N 4.84;
S 5.54.
1. Avdeenko, A.P., Konovalova, S.A., Ledeneva, O.P.,
Ludchenko, O.N., Palamarchuk, G.V., Zubatyuk, R.I.,
and Shishkin, O.V., Russ. J. Org. Chem., 2011, vol. 47,
p. 1508.
2. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org.
Chem., 2006, vol. 42, p. 349.
3. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org.
Chem., 2006, vol. 42, p. 669.
N′-(4-Chlorophenylsulfonyl)-N-[2,5-dibromo-
3-methyl-4-oxo-6-(propan-2-yl)cyclohexa-2,5-dien-
1-ylidene]benzimidamide (XXIVc). Yield 71%,
4. Avdeenko, A.P., Konovalova, S.A., and Ludchen-
1
ko, O.N., Russ. J. Org. Chem., 2006, vol. 42, p. 683.
mp 131–133°C. H NMR spectrum (CDCl3), δ, ppm:
5. Avdeenko, A.P., Pirozhenko, V.V., Shishkin, O.V.,
Shishkina, S.V., Konovalova, S.A., and Ludchen-
ko, O.N., Russ. J. Org. Chem., 2008, vol. 44, p. 542.
6. Avdeenko, A.P., Pirozhenko, V.V., Shishkin, O.V., Pala-
marchuk, G.V., Zubatyuk, R.I., Konovalova, S.A., and
Ludchenko, O.N., Russ. J. Org. Chem., 2008, vol. 44,
p. 807.
1.47 d.d (6H, 6-CHMe2, J = 7.2, 18 Hz), 2.26 s (3H,
3-Me), 3.76–3.84 m (1H, 6-CH), 7.44–7.77 m (5H,
Ph), 7.49 d (2H, 3′-H, 5′-H, J = 8.1 Hz), 7.94 d (2H,
2′-H, 6′-H, J = 8.1 Hz). Found, %: Br+Cl 32.30,
32.51; N 4.72, 4.88; S 5.19, 5.39. C23H19Br2ClN2O3S.
Calculated, %: Br+Cl 32.61; N 4.68; S 5.36.
Reaction of quinone imines XXIIIb and XXIIIc
with methanol (general procedure). A solution of
1.1 mmol of compound XXIIIb and XXIIIc in 4 ml of
methanol was heated under reflux with protection from
atmospheric moisture until the initial quinone imine
disappeared according to the TLC data (reaction time
36 and 30 h, respectively). The mixture was cooled,
and the colorless crystalline product was filtered off,
washed with methanol, and dried.
7. Avdeenko, A.P., Konovalova, S.A., Ludchenko, O.N.,
Palamarchuk, G.V., and Shishkin, O.V., Russ. J. Org.
Chem., 2009, vol. 45, p. 1651.
8. Avdeenko, A.P., Konovalova, S.A., and Ludchen-
ko, O.N., Russ. J. Org. Chem., 2009, vol. 45, p. 1799.
9. Burmistrov, K.S. and Burmistrov, S.I., Zh. Org. Khim.,
1980, vol. 16, p. 1487.
10. Burmistrov, K.S., Toropin, N.V., Vakulenko, A.V.,
Yurchenko, A.G., and Markov, V.I., Vopr. Khim. Khim.
Tekhnol., 2000, no. 2, p. 30.
11. Petrova, S.A., Burmistrov, K.S., Kolodyazhnyi, M.V.,
and Ksenzhek, O.S., Elektrokhimiya, 1979, vol. 15,
p. 1666.
N-[2,5-Dibromo-1-methoxy-6-methyl-4-oxo-
3-(propan-2-yl)cyclohexa-2,5-dien-1-yl]-N′-(4-meth-
ylphenylsulfonyl)benzimidamide (XXVa). Yield
1
80%, mp 164–167°C. H NMR spectrum (CDCl3), δ,
12. Avdeenko, A.P., Burmistrov, K.S., Dubina, V.L., and
ppm: 0.98 d and 1.18 d (3H each, 3-CHMe2, J =
6.9 Hz), 2.18 s (3H, 6-Me), 2.38 s (3H, MeC6H4),
3.01 s (3H, MeO), 3.20–3.30 m (1H, 3-CH), 5.90 br.s
(1H, NH), 7.17 d (2H, 3′-H, 5′-H, J = 8.2 Hz), 7.47–
7.75 m (5H, Ph), 7.48 d (2H, 2′-H, 6′-H, J = 8.2 Hz).
Found, %: Br 26.30, 26.25; N 4.40, 4.52; S 5.20, 5.10.
C25H26Br2N2O4S. Calculated, %: Br 26.18; N 4.59;
S 5.25.
Skripets, V.I., Ukr. Khim. Zh., 1980, vol. 46, p. 1081.
13. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A.,
Burmistrov, K.S., Nichvoloda, V.M., Shishkin, O.V.,
Zubatyuk, R.I., and Palamarchuk, G.V., Russ. J. Org.
Chem., 2009, vol. 45, p. 48.
14. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A.,
Ludchenko, O.N., and Marchenko, I.L., Russ. J. Org.
Chem., 2009, vol. 45, p. 383.
N′-(4-Chlorophenylsulfonyl)-N-[2,5-dibromo-1-
methoxy-6-methyl-4-oxo-3-(propan-2-yl)cyclohexa-
15. Avdeenko, A.P., Marchenko, I.L., and Konovalo-
va, S.A., Russ. J. Org. Chem., 2002, vol. 38, p. 546.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 7 2012