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(s, 1H, CH), 7.60 (d, 1H, J ¼ 8.32 Hz, CH), 7.20 (t, 2H, J ¼ 7.72 Hz, CH), 6.97 (t, 1H,
J ¼ 7.49 Hz, CH), 6.87 (d, 1H, J ¼ 7.89 Hz, CH), 4.93 (s, 1H, CH2) ppm; IR (KBr,
cmꢀ1): 3220, 3140, 3080, 2930, 1680, 1610, 1480, 1420, 1320, 1220, 1140, 1100,
750, 730; EI-MS (m=z, %) 286 (Mþ, 3.83), 147 (C8H7N2Oþ, 100.00), 148
(C8H8N2Oþ, 21.21), 132 (C8H6NOþ, 3.31), 104 (C2H6Nþ, 3.95), 77 (C6Hþ5 , 3.58).
Anal. calcd. for C14H11ClN4O: 286.0626. Found: 286.0628.
3-[(Thiophene-3-yl-methylene)amino]-benzo[b]pyrimidin-2-one (13b). Yield:
75%; mp: 238.2–240.0 ꢁC; 1H NMR (DMSO-d6, 500 MHz): d 9.75 (s, 1H, NH), 8.13
(s, 1H, CH), 7.84 (d, 1H, J ¼ 2.23 Hz, CH), 7.61 (dd, 1H, J ¼ 3.07 Hz, 2.85 Hz, CH),
7.49 (d, 1H, J ¼ 5.03 Hz, CH), 7.23–7.18 (m, 2H, CH), 6.96 (t, 1H, J ¼ 7.46 Hz, CH),
6.87 (d, 1H, J ¼ 7.94 Hz, CH), 4.88 (s, 2H, CH2) ppm; IR (KBr, cmꢀ1): 3400, 3200,
3080, 2920, 2890, 1680, 1610, 1480, 1430, 1320, 1220, 750; EI-MS (m=z, %) 257 (Mþ,
3.83), 147 (C8H7N2Oþ, 100.00), 148 (C8H8N2Oþ, 21.21), 132 (C8H6NOþ, 3.31), 104
(C2H6Nþ, 3.95), 77 (C6H5þ, 3.58). Anal. calcd. for C13H11N3OS: 257.0620. Found:
257.0623.
3-[(2-Chloro-thiazole-3-yl-methylene)amino]-benzo[b]pyrimidin-2-one
1
(13c). Yield: 78%; Mp: 231.6–233.0 ꢁC; H NMR (DMSO-d6, 500 MHz): d 9.93 (s,
1H, NH), 8.24 (s, 1H, CH), 7.94 (s, 1H, CH), 7.19 (t, 2H, J ¼ 7.44 Hz, 7.54 Hz, CH),
6.97 (t, 1H, J ¼ 7.40 Hz, CH), 6.85 (d, 1H, J ¼ 7.91 Hz, CH), 4.89 (s, 2H, CH2) ppm;
IR (KBr, cmꢀ1): 3230, 3100, 2980, 1700, 1610, 1480, 1410, 1320, 1220, 1050, 750,
730, 600; EI-Ms(m=z, %) 292 (Mþ, 3.23), 147 (C8H7N2Oþ, 100.00), 148 (C8H8N2Oþ,
18.20), 132 (C8H6NOþ, 8.06), 104 (C2H6Nþ, 5.83), 77 (C6H5þ, 4.73). Anal. calcd. for
C12H9ClN4OS: 292.0194. Found: 292.0192.
3-[(Furan-3-yl-methylene)amino]-benzo[b]pyrimidin-2-one (13d). Yield:
70%; mp: 234.9–236.0 ꢁC; 1H NMR (DMSO-d6, 500 MHz): d 9.80 (s, 1H, NH), 8.16
(s, 1H, CH), 8.01 (d, 1H, J ¼ 1.57 Hz, CH), 7.17 (t, 2H, J ¼ 7.53 Hz, 7.56 Hz, CH),
7.13 (d, 1H, J ¼ 2.11 Hz, CH), 7.03 (d, 1H, J ¼ 1.63 Hz, CH), 6.90 (t, 1H, J ¼ 7.43 Hz,
Hz, CH), 6.83 (d, 1H, J ¼ 7.93 Hz, CH), 4.74 (s, 2H, CH2) ppm; IR (KBr, cmꢀ1):
3400, 3200, 3080, 2920, 2890, 1680, 1610, 1480, 1400, 1320, 1210, 750; EI-MS (m=
z, %) 241 (Mþ, 5.52), 147 (C8H7N2Oþ, 100.00), 148 (C8H8N2Oþ, 18.84), 132
(C8H6NOþ, 5.01), 104 (C2H6Nþ, 4.80), 77 (C6Hþ5 , 4.55). Anal. calcd. for
C13H11N3O2: 241.0852. Found: 241.0855.
3-[(Indole-3-yl-methylene)amino]-benzo[b]pyrimidin-2-one (13e). Yield:
90%; mp: 218.0–220.3 ꢁC; 1H NMR (DMSO-d6, 500 MHz): d 9.65 (s, 1H, NH), 8.39
(s, 1H, NH), 8.38 (s, 1H, CH), 7.84 (s, 1H, CH), 7.46 (d, 1H, J ¼ 8.03 Hz, CH),
7.27–7.14 (m, 5H, Ar-H), 6.95 (t, 1H, J ¼ 7.40 Hz, CH), 6.89 (d, 1H, J ¼ 7.91 Hz,
CH), 4.91 (s, 2H, J ¼ 1.63 Hz, CH2) ppm; IR (KBr, cmꢀ1): 3240, 3080, 2980, 2920,
1700, 1500, 1320, 1480, 1220, 1750; EI-MS (m=z, %) 290 (Mþ, 7.81), 147 (C8H7N2Oþ,
, 100.00), 148 (C8H8N2Oþ, 15.59), 132 (C8H6NOþ, 3.44), 104 (C2H6Nþ, 3.30), 77
(C6Hþ5 , 3.51). Anal. calcd. for C17H14N4O: 290.1176. Found: 290.1172.
ACKNOWLEDGMENTS
This work was financial supported by National Basic Research Program
of China (973 Program, 2010CB126100), National High Technology Research,