9772
D.-Q. Shi et al. / Tetrahedron 63 (2007) 9764–9773
ꢁ
1
ꢁ1
IR (KBr, n, cm ): 3208, 3044, 2919, 1718, 1594, 1553,
1
9
IR (KBr, n, cm ): 3221, 3043, 2920, 1712, 1596, 1550,
1488, 1436, 1408, 1364, 1329, 1223, 1157, 1059, 840,
811, 753, 741.
500, 1475, 1435, 1364, 1311, 1211, 1169, 1076, 1020,
18, 879, 834, 816, 766, 751, 696.
1
1
H NMR (DMSO-d ) d: 7.23–7.29 (m, 3H, ArH), 7.43–7.47
6
H NMR (DMSO-d ) d: 7.15 (t, J¼8.8 Hz, 2H, ArH), 7.28
6
(m, 5H, ArH), 7.59–7.66 (m, 3H, ArH), 7.92–7.94 (m, 1H,
ArH), 8.17–8.19 (m, 1H, ArH), 11.86 (s, 1H, NH).
(t, J¼8.8 Hz, 2H, ArH), 7.37 (d, J¼8.4 Hz, 1H,
ArH), 7.46–7.52 (m, 4H, ArH), 7.60 (dd, J ¼2.4 Hz,
1
J ¼8.8 Hz, 1H, ArH), 8.17 (d, J¼2.4 Hz, 1H, ArH), 11.88
2
Anal. Calcd for C H ClN O: C 71.07, H 3.80, N 11.30;
3
(s, 1H, NH).
2
2
14
found: C 71.12, H 3.85, N 11.36.
Anal. Calcd for C H ClF N O: C 64.80, H 2.97, N 10.30;
2
2
12
2 3
4.6.7. 9-Chloro-2,3-di(4-methylphenyl)imidazo[1,2-
c]quinazolin-5(6H)-one (12g). Colorless crystals, mp
found: C 64.87, H 3.02, N 10.36.
ꢀ
>
300 C.
4.6.11. 8,9-Dimethoxy-2,3-diphenylimidazo[1,2-c]quin-
ꢀ
azolin-5(6H)-one (12k). Colorless crystals, mp >300 C.
ꢁ1
IR (KBr, n, cm ): 3215, 3038, 2917, 1710, 1592, 1549,
ꢁ
1
1
9
476, 1438, 1384, 1365, 1327, 1268, 1161, 1076, 1007,
11, 867, 839, 821, 753, 735, 712.
IR (KBr, n, cm ): 3198, 3056, 2998, 2934, 1725, 1667,
1612, 1560, 1507, 1441, 1413, 1389, 1349, 1279, 1217,
1
177, 1133, 1101, 1022, 999, 786, 743, 709, 697.
1
H NMR (DMSO-d ) d: 2.27 (s, 3H, CH ), 2.40 (s, 3H, CH ),
6
3
3
1
7
7
.08 (d, J¼8.0 Hz, 2H, ArH), 7.23 (d, J¼7.6 Hz, 2H, ArH),
H NMR (DMSO-d ) d: 3.84 (s, 3H, OCH ), 3.90 (s, 3H,
6 3
.31 (d, J¼8.0 Hz, 2H, ArH), 7.35–7.37 (m, 3H, ArH), 7.59
OCH ), 6.90 (s, 1H, ArH), 7.21–7.28 (m, 3H, ArH), 7.41–
3
7.47 (m, 7H, ArH), 7.61 (s, 1H, ArH), 11.50 (s, 1H, NH).
(
1
dd, J ¼2.0 Hz, J ¼8.4 Hz, 1H, ArH), 8.17 (d, J¼2.0 Hz,
1
2
H, ArH), 11.81 (s, 1H, NH).
Anal. Calcd for C H N O : C 72.53, H 4.82, N 10.57;
2
4 19 3 3
Anal. Calcd for C H ClN O: C 72.09, H 4.54, N 10.51;
2
found: C 72.64, H 4.86, N 10.63.
4
18
3
found: C 72.16, H 4.58, N 10.46.
4
.6.12. 8,9-Dimethoxy-2,3-di(4-bromophenyl)imid-
azo[1,2-c]quinazolin-5(6H)-one (12l). Pale yellow crystals,
4.6.8. 9-Chloro-2,3-di(4-methoxyphenyl)imidazo[1,2-
c]quinazolin-5(6H)-one (12h). Colorless crystals, mp
ꢀ
mp >300 C.
ꢀ
>
300 C.
ꢁ
1
IR (KBr, n, cm ): 3163, 3010, 2929, 1703, 1668, 1628,
1572, 1506, 1474, 1438, 1420, 1392, 1357, 1282, 1237,
1219, 1135, 1109, 1069, 1009, 828, 788, 753, 715.
ꢁ1
IR (KBr, n, cm ): 3208, 3090, 2955, 2834, 1701, 1612,
553, 1518, 1482, 1448, 1365, 1287, 1246, 1170, 1067,
037, 907, 867, 841, 827, 751, 741.
1
1
1
H NMR (DMSO-d ) d: 3.84 (s, 3H, OCH ), 3.89 (s, 3H,
6
3
1
H NMR (DMSO-d ) d: 3.73 (s, 3H, OCH ), 3.84 (s, 3H,
6
OCH ), 6.89 (s, 1H, ArH), 7.39 (d, J¼8.0 Hz, 4H, ArH),
3
3
OCH ), 6.85 (d, J¼8.8 Hz, 2H, ArH), 6.99 (d, J¼8.8 Hz,
7.50 (d, J¼8.0 Hz, 2H, ArH), 7.58 (s, 1H, ArH), 7.61 (d,
J¼8.0 Hz, 2H, ArH), 11.59 (s, 1H, NH).
3
2
2
8
H, ArH), 7.34–7.36 (m, 3H, ArH), 7.42 (d, J¼8.8 Hz,
H, ArH), 7.58 (dd, J ¼1.6 Hz, J ¼8.8 Hz, 1H, ArH),
1
2
.15 (d, J¼1.6 Hz, 1H, ArH), 11.78 (s, 1H, NH).
Anal. Calcd for C H Br N O : C 51.92, H 3.09, N 7.57;
2
found: C 51.96, H 3.04, N 7.61.
4
17
2 3 3
Anal. Calcd for C H ClN O : C 66.75, H 4.20, N 9.73;
3 3
24
18
found: C 66.82, H 4.16, N 9.81.
Acknowledgements
4
azolin-5(6H)-one (12i). Pale yellow crystals, mp >300 C.
.6.9. 9-Chloro-2,3-di(4-bromophenyl)imidazo[1,2-c]quin-
ꢀ
We are grateful to the National Natural Science Foundation
of China (20472062 and 20672079), the Natural Science
Foundation of Jiangsu Province (BK2006048), and the Nat-
ural Science Foundation of Jiangsu Education Department
(06KJA15007) for financial support.
ꢁ1
IR (KBr, n, cm ): 3216, 3041, 2919, 1715, 1596, 1549,
1
7
493, 1473, 1435, 1362, 1331, 1069, 1006, 841, 826, 799,
52, 734, 699.
1
H NMR (DMSO-d ) d: 7.36–7.42 (m, 5H, ArH), 7.52
6
(
d, J¼8.4 Hz, 2H, ArH), 7.59–7.62 (dd, J ¼2.0 Hz,
References and notes
1
J ¼8.8 Hz, 1H, ArH), 7.64 (d, J¼8.4 Hz, 2H, ArH), 8.17
2
(
d, J¼2.0 Hz, 1H, ArH), 11.91 (s, 1H, NH).
1. (a) McMurry, J. E. Acc. Chem. Res. 1974, 7, 281; (b) McMurry,
J. E. Acc. Chem. Res. 1983, 16, 405; (c) McMurry, J. E. Chem.
Rev. 1989, 89, 1513; (d) Lenoir, D. Synthesis 1989, 883; (e)
F €u rstner, A.; Bogdanovi, B. Angew. Chem., Int. Ed. 1996, 35,
Anal. Calcd for C H Br ClN O: C 49.89, H 2.28, N 7.93;
3
found: C 50.01, H 2.25, N 7.98.
2
2
12
2
2
443; (f) Shi, D. Q.; Chen, J. X.; Chai, W. Y.; Chen, W. X.;
4.6.10. 9-Chloro-2,3-di(4-fluorophenyl)imidazo[1,2-
c]quinazolin-5(6H)-one (12j). Colorless crystals, mp
Kao, T. Y. Tetrahedron Lett. 1993, 34, 2963.
2. Zhou, L. H.; Shi, D. Q.; Gao, Y.; Shen, W. B.; Dai, G. Y.; Chen,
W. X. Tetrahedron Lett. 1997, 38, 2729.
ꢀ
>
300 C.