3612
Kovtunenko, Potikha, and Turov
C(3)HAHB), 4.08 (d, 1 H, 2J ¼ 18.6 Hz, C(3)HAHB); 13C NMR (DMSO-d6):
d 197.12 (CO); 155.22 (C-8a); 145.14 (C-5); 143.96, 137.75, 136.77,
134.06, 129.18 (3C), 128.61 (2C), 128.14, 125.85 (2C) (2C6H5); 114.06
(C-8); 109.91 (C-6); 96.28 (C-7); 65.86 (C-2); 63.38 (C-3); 48.88
(CH2CO). Anal. calcd for C21H19BrN2O: C 63.81, H 4.84, Br 20.21, N
7.09. Found: C 63.79, H 4.80, Br 20.20, N 7.13.
2-Phenacyl-2-phenyl-2,3-dihydro-1H 1-imidazo[1,2-a]pyrimidinium
bromide (4). Compound 4 was prepared by the procedure described for 3,
using 3.38 g (35.5 mmol) of 2-aminopyrimidine. Yield, 7.03 g (50%); Mp:
209–2118C (CH3CN); IR (KBr): n 3440 (N–H), 1680 (C55O), 1645
1
(C55Nþ) cm21; H NMR (DMSO-d6): d 10.85 (s, 1 H, NH), 8.95 (m, 1 H,
3
5-H), 8.89 (m, 1 H, 7-H), 7.92 (d, 2 H, J ¼ 8.0 Hz, 200-H, 600-H), 7.60
3
3
(t, 1 H, J ¼ 7.2 Hz, 400-H), 7.59 (d, 2 H, J ¼ 8.0 Hz, 20-H, 60-H), 7.48
3
3
(t, 2 H, J ¼ 8.0 Hz, 300-H, 500-H), 7.42 (t, 2H, J ¼ 7.6 Hz, 30-H, 50-H),
3
7.32 (t, 1 H, J ¼ 7.6 Hz, 40-H), 7.16 (m, 1 H, 6-H), 5.34 (d, 1 H,
2J ¼ 13.6 Hz, CHAHBCO), 4.93 (d, 1 H, J ¼ 13.6 Hz, CHAHBCO), 4.25
2
2
2
(d, 1 H, J ¼ 18.8 Hz, C(3)HAHB), 4.06 (d, 1 H, J ¼ 18.8 Hz, C(3)HAHB);
13C NMR (DMSO-d6): d 197.69 (CO); 168.31 (C-8a); 157.67 (C-7);
148.59 (C-5); 144.20, 136.81, 134.47, 129.50 (2C), 129.45 (2C), 128.69
(2C), 128.56, 126.03 (2C) (2C6H5); 111.27 (C-6); 63.71 (C-2); 61.29 (C-
3); 48.91 (CH2CO). Anal. calcd for C20H18BrN3O: C 60.62, H 4.58, Br
20.16, N 10.60. Found: C 60.59, H 4.56, Br 20.19, N 10.63.
2-Phenynacyl-2-phenyl-2,3-dihydro-1H 1-imidazo[2,1-b]benzothia-
zolium bromide (5). Compound 5 was prepared as described for 3, using
5.33 g (35.5 mmol) of 2-aminobenzothiazole. Yield, 9.77 g (61%); Mp:
144–1468C (CH3CN); IR (KBr): n 3440 (N–H), 1675 (C55O), 1640
1
(C55Nþ) cm21; H NMR (DMSO-d6): d 8.40 (bs, 1 H, NH), 8.06 (d, 1 H,
3
3J ¼ 8.0 Hz, 5-H), 7.97 (d, 2 H, J ¼ 8.0 Hz, 200-H, 600-H), 7.67 (d, 1 H,
3
3J ¼ 8.0 Hz, 8-H), 7.62 (t, 1 H, J ¼ 7.2 Hz, 400-H), 7.59 (d, 2 H,
3J ¼ 8.0 Hz, 20-H, 60-H), 7.55–7.48 (m, 2 H, 300-H, 500-H), 7.43–7.34 (m, 2
3
3
H, 30-H, 50-H), 7.32 (t, 1 H, J ¼ 7.6 Hz, 40-H), 7.26 (t, 1 H, J ¼ 8.0 Hz,
7-H), 7.09 (t, 1 H, 3J ¼ 8.0 Hz, 6-H), 5.03 (d, 1 H, 2J ¼ 10.8 Hz,
CHAHBCO), 4.66 (d, 1 H, 2J ¼ 10.8 Hz, CHAHBCO), 4.63 (d, 1 H,
2J ¼ 19.2 Hz, C(3)HAHB), 4.30 (d, 1 H, 2J ¼ 19.2 Hz, C(3)HAHB); 13C
NMR (DMSO-d6): d 197.54 (CO); 170.06 (C-9a); 168.04, 147.55, 142.83,
136.52, 135.21, 134.48, 129.41, 128.61(2C), 127.96, 126.83, 125.77,
125.47, 125.21, 122.77, 122.38, 116.81, 113.44 (C6H4, 2C6H5); 74.35 (C-
2); 59.01 (C-3); 48.09 (CH2CO). Anal. calcd for C23H19BrN2OS: C 61.20,
H 4.24, Br 17.70, N 6.21, S 7.10. Found: C 61.19, H 4.27, Br 17.71, N
6.26, S 7.13.
2-Phenylimidazo[1,2-a]pyridine (6). To a solution of 2-phenacyl-2-phenyl-
2,3-dihydro-1Hþ-imidazo[1,2-a]pyridinium bromide 3 (1 g, 2.5 mmol) in