chloride filtrate gave an addition 0.036 g (15%) chloride 1, mp 170–172°C. IR spectrum, , cm–1: 1618, 1589,
1533, 1373, 1273, 1194, 1039, 824, 762, 582. Found, %: C 44.47; H 2.42; N 5.75. C9H6ClNSe. Calculated, %:
C 44.58; H 2.49; N 5.78.
Reactions of 8-Quinolineselanyl Chloride 1 with Unsaturated Compounds 2 and 3. (General
Method). A solution of unsaturated compounds 2 or 3 (0.4 mmol) in methylene chloride (5 ml) was added to a
suspension of selanyl chloride 1 (0.097 g, 0.4 mmol) in methylene chloride (15 ml) at 20°C. In 48 h, after
complete dissolution of selanyl chloride 1, the solvent was evaporated in vacuum. Recrystallization of the
residue from methylene chloride gave compounds 4 or 5.
cis-8,12b-Dihydro-7aH-indeno[1',2':5,6][1,4]selenazino[2,3,4-i,j]quinolinium-13 Chloride (4) was
obtained in 91% yield; mp 230–232°C. IR spectrum, , cm–1: 1609, 1557, 1478, 1429, 1288, 1175, 788, 761.
2
2
3
1H NMR spectrum, , ppm (J, Hz): 3.27 (1H, d, J = 16.8, H-8); 3.63 (1H, dd, J = 16.8, J = 4.7, H-8); 4.88
3
3
3
3
(1H, t, J = 4.7, H-7a); 6.62 (1H, d, J = 7.6, H-12); 6.92 (1H, d, J = 4.7, H-12b); 7.16 (1H, t, J = 7.5, H-11);
7.36 (1H, t, J = 7.5, H-10); 7.50 (1H, d, J = 7.5, H-9); 7.85 (1H, t, J = 7.8, H-5); 8.25 (1H, dd, J = 7.5,
J = 1.3, H-6); 8.30 (1H, dd, J = 8.1, J = 1.3, H-4); 8.39 (1H, dd, J =8.3, J = 5.8, H-2); 9.49 (1H, dd, J = 8.4,
J = 1.4, H-3); 9.76 (1H, dd, J = 6.0, J = 1.3, H-1). Found, %: C 60.10; H 3.83; N 3.84. C18H14ClNSe.
3
3
3
3
3
3
3
3
3
Calculated, %: C 60.28; H 3.93; N 3.91.
3-Phenyl-2,3-dihydropyrido[1,4]selenazino[2,3,4,-i,j]quinolinium-4 Chloride (5) was obtained in
1
82% yield; mp 130–132°C. IR spectrum, , cm–1: 1608, 1552, 1481, 1431, 1292, 1170, 796, 765. H NMR
2
3
2
3
spectrum,, ppm (J, Hz): 3.87 (1H, dd, J = 13.2, J = 4.4, H-2); 4.12 (1H, dd, J = 13.2, J = 2.9, H-2); 6.77
3
3
3
3
(1H, t, J = 4.4, J = 2.9, H-3); 6.81, 7.07, and 7.35 (5H, all br. s, 1:1:3, C6H5); 7.89 (1H, t, J = 8.8, J = 7.3,
H-9); 8.23 (1H, dd, 3J = 8.8, 3J = 5.9, H-6); 8.33 (1H, d, 3J = 7.3, H-10); 8.45 (1H, d, 3J = 8.8, H-8); 9.45 (1H, d,
3J = 8.8, H-7); 9.63 (1H, d, J = 5.9, H-5). Found, %: C 58.81; H 3.98; N 3.95. C17H14ClNSe. Calculated, %:
3
C 58.90; H 4.07; N 4.04.
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2.
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4.
A. V. Borisov, V. K. Osmanov, G. N. Borisova, Zh. V. Matsulevich, and G. K. Fukin, Mendeleev
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