HETEROCYCLES, Vol. 87, No. 8, 2013
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NMR (DMSO-d6) δ 2.43 (s, 3H), 7.39 (d, 2H, J = 7.8 Hz), 7.46 (t, 1H, J = 2.4 Hz), 7.82 (d, 2H, J = 7.8
Hz), 8.42 (s, 1H), 8.86 (d, 1H, J = 3.6 Hz), 9.87 (d, 1H, J = 6.9 Hz); 13C NMR (DMSO-d6) δ 21.62,
112.26, 121.84, 129.48, 129.83, 135.79, 137.35, 143.30, 146.00, 151.36, 154.73, 184.21. MS m/z 237
(M+). Anal. Calcd for C14H11N3O: C, 70.87; H, 4.67; N, 17.71. Found: C, 70.84; H, 4.63; N, 17.68%.
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3-(4-Bromobenzoyl)imidazo[1,2-a]pyrimidine (5c): mp 248 ˚C; IR (KBr) νmax/cm-1 1698 (C=O); H
NMR (DMSO-d6) δ 7.45 (t, 1H, J = 7.8 Hz), 7.77-7.81 (m, 4H), 8.46 (s, 1H), 8.88 (d, 1H, J = 3.6 Hz),
9.85 (d, 1H, J = 6.9 Hz). MS m/z 302 (M+). Anal. Calcd for C13H8BrN3O: C, 51.68; H, 2.67; N, 13.91.
Found: C, 51.65; H, 2.66; N, 13.93%.
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3-(4-Chlorobenzoyl)imidazo[1,2-a]pyrimidines (5d): mp 240 ˚C; IR (KBr) νmax/cm-1 1699 (C=O); H
NMR (DMSO-d6) δ 7.46 (t, 1H, J = 2.4 Hz), 7.66 (d, 2H, J = 7.8 Hz), 7.92 (d, 2H, J = 7.8 Hz), 8.46 (s,
1H), 8.88 (d, 1H, J = 3.6 Hz), 9.86 (d, 1H, J = 6.9 Hz). MS m/z 257 (M+). Anal. Calcd for C13H8 ClN3O:
C, 60.60; H, 3.13; N, 16.31. Found: C, 60.62; H, 3.11; N, 16.34%.
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3-(4-Fluorobenzoyl)imidazo[1,2-a]pyrimidine (5e): mp 256 ˚C; IR (KBr) νmax/cm-1 1698 (C=O); H
NMR (DMSO-d6) δ 7.39 (t, 1H, J = 2.4 Hz), 7.46 (d, 2H, J = 7.8 Hz), 7.98 (d, 2H, J = 7.8 Hz), 8.44 (s,
1H), 8.88 (d, 1H, J = 3.6 Hz), 9.86 (d, 1H, J = 6.9 Hz). MS m/z 241 (M+). Anal. Calcd for C13H8 FN3O: C,
64.73; H, 3.34; N, 17.42. Found: C, 64.70; H, 3.32; N, 17.40%.
3-(4-Trifluoroacetamidobenzoyl)imidazo[1,2-a]pyrimidine (5f): mp 235 ˚C; IR (KBr) νmax/cm-1 3568,
(NH), 1737 (C=O), 1615 (C=O); 1H NMR (DMSO-d6) δ 7.46 (t, 1H, J = 2.4 Hz), 7.93 (d, 2H, J = 7.8 Hz),
7.99 (d, 2H, J = 7.8 Hz), 8.48 (s, 1H), 8.87 (d, 1H, J = 3.6 Hz), 9.87 (d, 1H, J = 6.9 Hz), 11.57 (s, 1H); 13C
NMR (DMSO-d6) δ 111.79, 117.53, 115.29, 121.06, 12171, 130.50, 135.12, 137.08, 140.57, 146.16,
150.74, 154.17 (q), 183.18. MS m/z 334 (M+). Anal. Calcd for C15H9 F3N4O2: C, 53.90; H, 2.71; N, 16.76.
Found: C, 53.88; H, 2.73; N, 16.72%.
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3-(Benzothiazol-2-oyl)imidazo[1,2-a]pyrimidine (8): mp 258 ˚C; IR (KBr) νmax/cm-1 1686 (C=O); H
NMR (DMSO-d6) δ 7.52-7.54 (m, 2H), 7.63 (t, 1H, J = 7.8 Hz), 8.29 (d, 1H, J = 7.8 Hz), 8.35 (d, 1H),
8.94 (d, 1H, J = 3.6 Hz), 9.59 (s, 1H), 9.96 (s, 1H). MS m/z 280 (M+). Anal. Calcd for C14H8N4OS: C,
59.99; H, 2.88; N, 19.99. Found: C, 59.97; H, 2.85; N, 19.96%.
Bis(imidazo[1,2-a]pyrimidines) 10a-d
10a: mp 261-262 ˚C; IR (KBr) νmax/cm-1 1624 (C=O); 1H NMR (DMSO-d6) δ 1.98 (m, 2H), 4.26 (m, 4H),
6.97 (d, 2H, J = 9 Hz), 7.03 (t, 2H, J = 9 Hz), 7.39-7.49 (m, 6H, J = 9 Hz), 8.08 (s, 2H), 8.86 (d, 2H, J = 9
Hz), 9.87 (d, 2H, J = 9 Hz); 13C NMR (DMSO-d6) δ 28.55, 65.44, 113.91, 120.94, 122.65, 128.08, 129.74,
132.62, 134.17, 136.98, 137.32, 146.89, 154.65, 156.20, 184.17. MS m/z 518 (M+). Anal. Calcd for
C29H22N6O4: C, 67.17; H, 4.28; N, 16.21. Found: C, 67.15; H, 4.25; N, 16.24%.
10b: mp 269-270 ˚C; IR (KBr) νmax/cm-1 1658 (C=O); 1H NMR (DMSO-d6) δ 1.47 (m, 4H), 3.92 (m, 4H),
6.98-7.09 (m, 4H, J = 9 Hz), 7.40-7.56 (m, 6H, J = 9 Hz), 8.07 (s, 2H), 8.84 (d, 2H, J = 9 Hz), 9.86 (d, 2H,