RESEARCH IN THE FIELD OF IMIDAZO[1,2-a]BENZIMIDAZOLE DERIVATIVES: XXVII.
285
3. Anisimova, V.A., Levchenko, M.V., Koshchienko, Yu.V.,
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Soedin., 1987, p. 59.
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Spasov,A.A., Kovalev, S.G., and Dudchenko, G.P., Patent
2691462, 1995; French Bull. 95/23.
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Caignard, D.-H., Renard, P., and Manechez, D., French
Patent 2765223, 1998.
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Takagi, H., Kobayashi, Sh., Kamioka, T., and Kamoshi-
ta, K., J. Med. Chem., 1972, vol. 15, p. 923.
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Soedin., 1976, p. 121.
19. Anisimova, V.A., Spasov, A.A., Ostrovskii, O.V., Dud-
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benzimidazole (XVIIc). Asolution of 0.6 g (2 mmol) of
base IIIc and 0.65 g (8 mmol) of anhydrous AcONa in
10 ml of Ac2O was boiled for 1 h, and the hygroscopic
diacetyl derivative XVIIc was isolated similarly to
compound XVc. Yield 0.63 g (83%), mp 132–133°C
(decomp., from octane). IR spectrum, ν, cm–1: 1735
(OCOCH3), 1690 (CH2CO), 1675 (NCOCH3). 1H NMR
spectrum (CDCl3), δ, ppm: 1.85 s (3H, COCH3), 1.96 s
(3H, COCH3), 3.97 t (2H, CH2O), 4.28 t (2H, NCH2),
5.50 s (2H, CH2CO), 7.07–7.85 m (7HAr), 8.02 d (2H,
H2',6'). Found, %: C 66.33; H 5.67; N 11.00. C21H21N3O4.
Calculated, %: C 66.48; H 5.58; N 11.07.
The reaction in the absence of AcONa led to the
same result.
2-(N-Acetylamino-3-acetoxypropyl)-1-phenacyl-
benzimidazole (XVIIIc). A mixture of 0.62 g (2 mmol)
of base IVc, 0.65 g (8 mmol) of anhydrous AcONa, and
4 ml ofAc2O was boiled for 1 h. Oily substance separated
after the cautious decomposition of excess Ac2O and
the neutralization of the solution was extracted into CHCl3,
and the extract was passed through the bed of Al2O3
(eluent CHCl3). The residue after the evaporation of the
eluate was ground with hexane. Yield 0.67 g (87%).
Hygroscopic crystals, mp 47–48°C (from octane). IR
spectrum, ν, cm–1: 1733 (OCOCH3), 1700 (CH2CO),
1
1680 (NCOCH3). H NMR spectrum (CDCl3), δ, ppm:
1.88–2.10 m (8H, 2CH3, CH2), 3.94–4.15 m (4H, NCH2,
CH2O), 5.46 s (2H, CH2CO), 7.05–7.86 m (7HAr), 8.02 d
(2H, H2',6'). Found, %: C 67.03; H 5.75; N 10.74.
C22H23N3O4. Calculated, %: C 67.16; H 5.89; N 10.68.
2-(N-Acetylamino-2-acetoxyethyl)-1-(2-thenoyl-
methyl)benzimidazole (XVIIe) was obtained by boiling
1.15 g (3 mmol) of compound IIIe hydrobromide and
1.5 g of anhydrous AcONa in 15 ml of AC2O over 1–
1.5 h. Yield 1.02 g (88%), mp 100–102°C (EtOAc). IR
spectrum, ν, cm–1: 1753 (OCOCH3), 1720 (CH2CO),
1
1686 (NCOCH3), 1666 (C=N). H NMR spectrum
(CDCl3), δ, ppm: 2.00 s (6H, 2CH3), 3.68 t (2H, CH2),
4.25 t (2H, CH2), 5.08 s (2H, CH2CO), 7.00–7.80 m
(7HAr). Found, %: C 59.39; H 5.21; N 11.17; S 8.12.
C19H19N3O4S. Calculated, %: C 59.20; H 4.97; N 10.90;
S 8.32.
21. Anisimova, V.A., Osipova, M.M., Galenko-Yaroshev-
skii,A.P., Ponomarev, V.V., Popkov, V.L., Prikhod’ko,A.K.,
Kade, E.A., and Spasov, A.A., Khim.-Farm. Zh., 2002,
vol. 36, no. 8, p. 21.
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