and 10 ml 10% aq. Na2CO3 was added. The solid was filtered off and thoroughly washed with water and a small
amount of 2-propanol. IR spectrum, ν, cm-1: 3065, 1600 (C=N), 1450, 1323, 755, 745, 693. 1H NMR spectrum,
3
3
δ, ppm (J, Hz): 8.97 (1H, s, H-4); 7.84 (1H, d, J = 8.0, H-6); 7.66 (2H, d, J = 8.0, H-2', H-6'); 7.56-7.54 (5H,
m, H-3', H-4', H-5', H-2", H-6"); 7.49 (2H, t, 3J = 8.0, H-3", H-5"); 7.36-7.35 (3H, m, H-8, H-9, H-4"); 7.15 (1H,
3
t, J = 8.0, H-7); 6.98 (1H, s, H-2). Chemical ionization mass spectrum, m/z (Irel, %): 321 [M+1]+ (100),
322 [M+2]+ (43).
1,3-Bis(4-chlorophenyl)pyrrolo[1,2-a]quinoxaline (6b) and 1,3-Bis(4-bromophenyl)pyrrolo-
[1,2-a]quinoxaline (6c) were obtained according to the procedure for quinoxaline 6a using 10 ml formic acid.
Quinoxaline 6b. IR spectrum, ν, cm-1: 3045, 1612 (C=N), 1491, 1470, 1425, 1324, 1090, 819, 766.
3
3
1H NMR spectrum, δ, ppm (J, Hz): 8.97 (1H, s, H-4); 7.86 (1H, d, J = 8.0, H-6); 7.67 (2H, d, J = 8.0, H-2',
H-6'); 7.57-7.56 (4H, m, H-3', H-5', H-2", H-6"); 7.48 (2H, t, 3J = 8.0, H-3", H-5"); 7.39-7.38 (2H, m, H-8, H-9);
7.22 (1H, t, 3J = 8.0, H-7); 7.00 (1H, s, H-2).
Quinoxaline 6с. IR spectrum, ν, cm–1: 3050, 1611 (C=N), 1470, 1422, 1324, 1075, 1006, 818, 765. 1Н
3
NMR spectrum, δ, ppm (J, Hz): 8.96 (1Н, s, Н-4); 7.85 (1Н, d, 3J = 8.0, Н-6); 7.69 (2Н, d, J = 8.0, H-2', H-6');
7.61 (4Н, m, H-3', H-5', H-2'', H-6''); 7.50 (2Н, t, 3J = 8.0, H-3'', H-5''); 7.39 (2Н, m, Н-8, H-9); 7.22 (1H, t, 3J =
8.0, Н-7); 7.00 (1H, s, H-2).
1-[7-(2,4-Diphenylpyrrol-1-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,4-diphenylpyrrole
(7).
A
mixture of γ-bromodypnone 2a (1.0 g, 3.32 mmol), sodium acetate (0.27 g), and (0.55 g, 3.32 mmol)
7-amino-2,3-dihydro-1,4-benzodioxin-6-ylamine was fused on an oil bath at 120-130°C for 5 min. After
cooling, 10 ml water was added to the melt and thoroughly triturated. The solid residue was filtered off,
thoroughly washed with water and 2-propanol, and recrystallized. IR spectrum, ν, cm-1: 1600, 1500, 1298, 1205
1
(C-O), 1065, 770, 700. H NMR spectrum, δ, ppm (J, Hz): 7.27-7.23 (9H, m, H Ar, 2H-α); 7.10-6.92 (11H, m,
H Ar); 6.73-6.71 (4H, m, H-5, H-8, 2H-4"); 6.38 (2H, br. s, 2H-β); 4.36-4.35 (4H, m, O(CH2)2O. Chemical
ionization mass spectrum, m/z (Irel, %): 571 [M+1]+ (100), 572 [M+2]+ (50).
1-{2-[(2,4-Diphenylpyrrol-1-yl)methyl]phenyl}-2,4-diphenylpyrrole (8) was obtained according to
the procedure described above for pyrrole 7 using 2-(aminomethyl)aniline (0.4 g, 3.32 mmol). IR spectrum,
ν, cm-1: 3027, 2937, 1600, 1490, 1395, 1230, 760, 690. 1H NMR spectrum, δ, ppm (J, Hz): 7.58 (2H, d, 3J = 8.5,
H-2', H-6'); 7.40 (2H, d, 3J = 8.0, H-2"', H-6"'); 7.35-7.33 (5H, m, H-3', H-4', H-5', H-2", H-6"); 7.26-7.24 (5H,
m, H-3'", H-4'", H-5'", H-2''", H-6'"'); 7.17-7.15 (6H, m, H-3", H-4", H-5", H-3"', H-4"', H-5"'); 7.08 (1H, t,
3J = 8.0, H-4); 6.99-6.97 (3H, m, H-5, H-6, H-α); 6.78 (1H, d, 3J = 1.6, H-β); 6.45 (1H, d, 3J = 1.6, H-β'); 4.94
(1H, d, 2J = 16.8, CHAHB); 4.73 (1H, d, 2J = 16.8, CHACHB).
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