for compound 2c), when compared to the analogous signals for the corresponding perimidines (7.08 ppm for
compound 1a, 7.04 ppm for compound 1b, and 7.08 ppm for compound 1c). The chemical shifts for the other
protons agree within experimental error, i.e. 6.44 and 6.46 ppm for the H-4,9 protons (compound 1a) and
H-4,4',9,9' (compound 2a), 7.03 ppm for protons H-5,7 (compound 1a) and 7.01 ppm for protons H-8,8' (7.04 ppm
for protons H-5,5' in the case of compound 2a). This observation confirms the proposed regioselectivity.
IR spectra were recorded on a Specord 75 IR instrument in KBr pellets. 1H NMR spectra were recorded
on a Bruker WP-200 instrument (200 MHz) using DMSO-d6 with TMS as internal standard. Assignment of the
signals was carried out using the double resonance method. Elemental analysis was performed on a KOVO
CHN-1 CHN analyzer. Melting points were measured on a PTP-M apparatus (Khimlaborpribor). Monitoring of
the reaction course and purity of the synthesized compounds was carried out on Silufol UV-254 plates using
EtOAc–EtOH (1:1) as eluent.
6(7),6'(7')-Biperimidinyls 2a-c (General Method). A mixture of the corresponding 1H-perimidine
1a-c (1 mmol), AlCl3 (0.40 g, 3 mmol) and nitromethane (5 ml) was stirred at room temperature for 36-48 h. At
the end of the reaction the mixture was poured into water (30 ml), and the precipitate formed was filtered off,
washed on the filter with a small amount of EtOAc, and dried. If needed, the product may be recrystallized from
EtOAc.
1H,1'H-[6,6']Biperimidinyl (2a). Yield 0.32 g (96%); mp > 300ºC (EtOAc). IR spectrum, , cm-1:
1640 (C=N), 3420 (NH). 1H NMR spectrum, , ppm (J, Hz): 6.45-6.47 (4H, m, H-4,9,4',9'); 6.58 (2H, d, J = 7.7,
H-7,7'); 7.01 (2H, dd, J = 7.7, J = 8.4, H-8,8'); 7.04 (2H, d, J = 7.3, H-5,5'); 7.50 (2H, s, H-2,2'); 12.70 (2H, br.
s, 2NH). Found, %: C 79.10; H 4.17; N 16.73. C22H14N4. Calculated, %: C 79.02; H 4.22; N 16.76.
2,2'-Dimethyl-1H,1'H-[6,6']biperimidinyl (2b). Yield 0.35 g (97%); mp > 300ºC (EtOAc). IR
spectrum, , cm-1: 1638 (C=N), 3440 (NH). 1H NMR spectrum, , ppm (J, Hz): 2.35 (6H, s, 2CH3); 6.64 (2H, d,
J = 8.4, H-9,9'); 6.75 (2H, d, J = 7.7, H-7,7'); 6.85 (2H, d, J = 7.8, H-4,4'); 7.16 (2H, dd, J = 7.7, J = 8.4,
H-8,8'); 7.21 (2H, d, J = 7.8, H-5,5'); 12.70 (2H, br. s, 2NH). Found, %: C 79.61; H 4.98; N 15.41. C24H18N4.
Calculated, %: C 79.54; H 5.01; N 15.46.
2,2'-Diphenyl-1H,1'H-[6,6']biperimidinyl (2c). Yield 0.47 g (97%); mp > 300ºC (EtOAc). IR
1
spectrum, , cm-1: 1640 (C=N), 3435 (NH). H NMR spectrum, , ppm (J, Hz): 6.61 (2H, d, J = 8.4, H-9,9');
6.88 (2H, d, J = 7.8, H-7,7'); 6.98 (2H, d, J = 7.8, H-4,4'); 7.11 (2H, dd, J = 7.8, J = 8.4, H-8,8'); 7.17 (2H, d,
J = 7.8, H-5,5'); 7.58-7.61 (6H, m, H-3,4,5 2Ph); 8.15 (4H, d, J = 8.4, H-2,6 2Ph); 12.70 (2H, br. s, NH). Found,
%: C 83.87; H 4.58; N 11.55. C34H22N4. Calculated, %: C 83.93; H 4.56; N 11.51.
This work was carried out within the Federal Target Program "Scientific and scientific-pedagogical
personnel of the innovative Russia" 2009-2013 (state contract No. 16.740.11.0162) and with financial support
from the Russian Foundation for Basic Research (grant 10-03-00193a).
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