2174
SARAEVA et al.
2-Amino-1-(benzimidazol-2-yl)-3-(4-methoxybenz-
Table 2. Bond angles (ω, deg) in structure II
oyl)indolizine (I) was synthesized according to the
Angle
ω, deg
Angle
ω, deg
procedure described in [1].
C21O2C24
C1N1C5
C1N1C8
C5N1C8
C9N2C16
C9N2C10
C16N2C10
C7N3C10
C9N4C11
C2C1N1
C1C2C3
C4C3C2
C3C4C5
N1C5C6
N1C5C4
C6C5C4
C7C6C5
C7C6C9
C5C6C9
N3C7C6
N3C7C8
C6C7C8
C7C8N1
C7C8C17
N1C8C17
N4C9N2
N4C9C6
N2C9C6
N3C10N2
117.74(12)
120.46(11)
129.24(12)
110.29(10)
105.62(10)
124.15(10)
129.40(10)
121.19(12)
104.26(10)
119.89(14)
120.89(13)
119.63(13)
119.60(13)
107.00(11)
119.50(11)
133.47(12)
108.21(11)
120.18(11)
131.26(12)
120.03(12)
130.06(12)
109.48(10)
104.91(11)
132.27(12)
122.54(11)
113.98(11)
128.65(11)
117.37(11)
108.78(10)
N3C10C26
N2C10C26
N3C10C25
N2C10C25
C26C10C25
N4C11C12
N4C11C16
C12C11C16
C13C12C11
C12N13C14
C15C14C13
C14C15C16
N2C16C15
N2C16C11
C15C16C11
O1C17C8
O1C17C18
C8C17C18
C23C18C19
C23C18C17
C19C18C17
C20C19C18
C19C20C21
O2C21C22
O2C21C20
C22C21C20
C23C22C21
C22C23C18
106.67(12)
111.45(12)
109.60(12)
108.13(11)
112.15(13)
128.63(12)
110.68(11)
120.68(12)
118.36(14)
120.91(14)
122.17(13)
117.14(14)
133.91(13)
105.37(10)
120.72(13)
121.68(13)
119.61(13)
118.70(11)
118.00(13)
118.82(13)
123.17(13)
120.89(13)
119.91(13)
124.75(13)
115.52(13)
119.73(13)
119.48(14)
121.71(14)
8-(4-Methoxybenzoyl)-6,6-dimethyl-6,7-dihydro-
benzo[4′,5′]imidazo[1′,2′ : 1,6]pyrimido[5,4-a]indo-
lizine (II). Indolizine I, 1 mmol, was dispersed in 15
ml of acetone, 3.0 mmol of methyl or ethyl iodide was
added, and the mixture was heated for 8 h under reflux.
After 24 h, the precipitate was filtered off and washed
with acetone. Yield 0.281 g (67%, MeI), 0.320 g (76%,
EtI), yellow powder, mp 240°C (from EtOH). IR
spectrum, ν, cm–1: 3410 (NH), 1644 (C=O). H NMR
1
spectrum, δ, ppm: 1.80 s (6H, Me), 3.86 s (3H, OMe),
5.46 s (1H, NH), 6.96 t (1H, 11-H, J = 6.94 Hz), 7.01–
7.31 m (4H, 4-H, 1-H, m-H), 7.46 t (1H, 12-H, J =
7.59 Hz), 7.54–7.64 m (2H, 3-H, 2-H), 7.70 d (2H, o-
H, J = 8.70 Hz), 8.08 d (1H, 13-H, J = 8.53 Hz), 9.30 d
(1H, 10-H, J = 7.02 Hz). Mass spectrum, m/z (Irel, %):
422 (82) [M]+, 407 (95.5) [M – CH3]+. Found, %: C
73.90; H 5.28; N 13.22. C26H22N4O2. Calculated, %: C
73.92; H 5.25; N 13.26.
X-Ray diffraction data for compound II.
Monoclinic crystals, C26H22N4O2; unit cell parameters
(298 K): a = 10.1901(3), b = 8.5336(3), c = 24.0462(7)
Å; β = 94.562(3)°; V = 2084.41(11) Å3; Mr = 422.48; Z
= 4; space group P21/c; dcalc = 1.346 g/cm3; μ(MoKα) =
0.088 mm–1; F(000) = 888. The unit cell parameters
and intensities of 23244 reflections (7001 independent
reflections, Rint = 0.026) were measured on an Xcalibur
3 automatic four-circle diffractometer (MoKα irradia-
tion, graphite monochromator, CCD detector, ω-
scanning, 2θmax = 65.06°). The structure was solved by
the direct method using SHELX-97 software package
[11]. The positions of hydrogen atoms attached to
carbon atoms were calculated on the basis of geometry
considerations and were refined according to the riding
model (Uiso = nUeq; n = 1.5 for methyl groups, and n =
1.2 for aromatic carbon atoms). The position of the
hydrogen atom on N3 was refined independently in
isotropic approximation. The structure was refined by
F2 using the full-matrix least-squares procedure in
anisotropic approximation for non-hydrogen atoms;
wR2 = 0.139 for 7001 reflections and R1 = 0.053 for
3967 reflections with F > 4σ(F); s = 1.00. The bond
lengths and bond angles in molecule II are given in
Tables 1 and 2, respectively. The complete set of
crystallographic parameters, coordinates of atoms, and
all bond lengths and bond angles were deposited to the
Cambridge Crystallographic Data Centre (entry no.
CCDC 771465).
EXPERIMENTAL
The IR spectra were recorded in KBr on a Perkin–
Elmer Spectrum One spectrometer. The 1H NMR
spectra were measured on a Bruker DRX-200 (200
MHz) and Bruker Avance II-400 (400 MHz)
instruments using DMSO-d6 as solvent and tetra-
methylsilane as internal reference. The mass spectra
(electron impact, 70 eV) were obtained on MKh-1321
and Varian 1200 L spectrometers with direct sample
admission into the ion source. The melting points were
determined on a Kofler hot stage. The progress of
reactions and the purity of products were monitored by
TLC on Silufol UV-254 plates using acetone–hexane
(3:5) as eluent; the chromatograms were developed by
treatment with iodine vapor or under UV light.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 10 2011